Table of the impacts of the COVID-19 pandemic on our financial results and business operations are currently unknown and cannot be estimated with any degree of certainty. Impacts to our financial results may include, without limitation, (1) negative impacts to our current and prospective users’ purchases or renewals of paid licenses for access to our platform, delays or defaults on payment obligations, which could negatively affect our revenues and cash flows, (2) modifications to net payment terms or invoice frequency, which could negatively affect our cash flows, (3) fluctuations in foreign currency exchange rates, which have and may in the future negatively impact our results of operations and cash flows, and (4) decreases in interest rates, which have and may continue to reduce interest income. Impacts to our business operations may include, without limitation, (1) disruptions to our sales operations and marketing efforts, (2) negative impacts to the financial condition or operations of our vendors and business partners, as well as disruptions to the supply chain of hardware needed to offer our services, (3) disruptions to our ability to conduct product development and other important business activities, and (4) potential postponement or cancellation of previously planned investments or other initiatives. In addition, economic effects related to the COVID-19 pandemic, such as ongoing supply chain disruption and labor shortages may affect us or our customers and vendors. Accordingly, the COVID-19 pandemic may have a negative impact on our financial results as well as our business operations, the magnitude and duration of which we are currently unable to predict. Additionally, concerns over the economic impact of the COVID-19 pandemic have caused extreme volatility in financial and other capital markets which may adversely impact our stock price.Contents

We generate revenue from sales of subscriptions to our platform, and any decline in demand for our platform or for content collaboration solutions in general could negatively impact our business.

We generate, and expect to continue to generate, revenue from the sale of subscriptions to our platform. As a result, widespread acceptance and use of content collaboration solutions in general, and our platform in particular, is critical to our future growth and success. If the content collaboration market fails to grow or grows more slowly than we currently anticipate, or if the current shift to remote or distributed work does not materialize into a longer-term trend, demand for our platform could be negatively affected.

Changes in user preferences for content collaboration may have a disproportionately greater impact on us than if we offered multiple platforms or disparate products. Demand for content collaboration solutions in general, and our platform in particular, is affected by a number of factors, many of which are beyond our control. Some of these potential factors include:

•awareness of the content collaboration category generally;

•availability of products and services that compete with ours;

•the impact, scale, and duration, of trends towards or away from remote or distributed work;

•ease of adoption and use;

•features and platform experience;

•performance;

~~Table of Contents~~

•brand;

•security and privacy;

•customer support; and

•pricing.

The content collaboration market is subject to rapidly changing user demand and trends in preferences. If we fail to successfully predict and address these changes and trends, meet user demands, or achieve more widespread market acceptance of our platform, our business, results of operations, and financial condition could be harmed.

~~Our business depends upon the interoperability of our platform across devices, operating systems, and third-party applications that we do not control.~~

One of the most important features of our platform is its broad interoperability with a range of diverse devices, operating systems, and third-party applications. Our platform is accessible from the web and from devices running Windows, Mac OS, iOS, Android, WindowsMobile, and Linux. We also have integrations with Microsoft, Adobe, Apple, Salesforce, Atlassian, Slack, BetterCloud, Google, IBM, Cisco, VMware, Okta, Symantec, Palo Alto Networks, Zoom, and a variety of other productivity, collaboration, data management, and security vendors. We are dependent on the accessibility of our platform across these third-party operating systems and applications that we do not control. Several of our competitors own, develop, operate, or distribute operating systems, app stores, third-party datacenter services, and other software, and also have material business relationships with companies that own, develop, operate, or distribute operating systems, applications markets, third-party datacenter services, and other software that our platform requires in order to operate. Moreover, some of these competitors have inherent advantages developing products and services that more tightly integrate with their software and hardware platforms or those of their business partners.

Third-party services and products are constantly evolving, and we may not be able to modify our platform to assure its compatibility with that of other third parties following development changes. In addition, some of our competitors may be able to disrupt the operations or compatibility of our platform with their products or services, or exert strong business influence on our ability to, and terms on which we, operate and distribute our platform. For example, we currently offer products that directly compete with several large technology companies that we rely on to ensure the interoperability of our platform with their products or services. We also rely on these companies to make our mobile applications available through their app stores. As our respective products evolve, we expect this level of competition to increase. Should any of our competitors modify their products or standards in a manner that degrades the functionality of our platform or gives preferential treatment to competitive products or services, whether to enhance their competitive position or for any other reason, the interoperability of our platform with these products could decrease and our business, results of operations, and financial condition could be harmed.

Failure to respond to rapid technological changes, extend our platform, or develop new features or products may harm our ability to compete effectively which would adversely affect our business.

The content collaboration market is characterized by rapid technological change and frequent new product and service introductions. Our ability to grow our user base and increase revenue from existing users will depend heavily on our ability to enhance and improve our platform, introduce new features and products, increase our strategic partnerships with third parties, and interoperate across an increasing range of devices, operating systems, and third-party applications. Users may require features and capabilities that our current platform does not have. In addition, while we believe current trends towards remote or distributed work will prove to be significant and long lasting, and that these trends will open up increased market opportunities for us, such trends or opportunities may not materialize or, if they do, we may not be able to develop new features or products, or enhance our existing offerings, sufficiently to take advantage of them. We invest significantly in research and development, and our goal is to focus our spending on measures that improve quality and ease of adoption and create organic user demand for our platform. For example, in 2020, we introduced Dropbox Passwords and Vault to provide additional security features for our users to safely store and access content on our platform. More recently, in 2021 we launched Dropbox Transfer as a way for users to safely and securely send large ~~files.~~files, Dropbox Shop which allows creators to easily sell content directly to their customers, Dropbox Replay, which allows users to review, approve and collaborate on video workflows, Backup, which allows users to securely back up their computer or external hard drives with an automated cloud backup solution, and Dropbox Capture which allows users to visually present their work through easy-to-take screen recordings, GIFs, and screenshots. There is no assurance that our enhancements to our platform or our new product experiences, partnerships, features, or capabilities will be compelling to our users or gain market acceptance. If our research and development investments do not accurately anticipate user demand, we are unsuccessful in establishing or maintaining our strategic partnerships, or if we fail to develop our platform

Table of Contents

in a manner that satisfies user preferences in a timely and cost-effective manner, we may fail to retain our existing users or increase demand for our platform.

The introduction of new products and services by competitors or the development of entirely new technologies to replace existing offerings could make our platform obsolete or adversely affect our business, results of operations, and financial

~~Table of Contents~~

condition. We may experience difficulties with software development, design, or marketing that could delay or prevent our development, introduction, or implementation of new product experiences, features, or capabilities. We also may experience broad-based business or economic disruptions that could adversely affect the productivity of our employees and result in delays in the development or implementation process. For example, as a result of the ongoing COVID-19 pandemic, we are temporarily requiring substantially all of our employees to work remotely, which may lead to disruptions and decreased productivity that could result in delays in our product development process. The risk of such disruptions and decreased productivity may persist as we continue to transition to a Virtual First workforce. We have in the past experienced delays in our internally planned release dates of new features and capabilities, and there can be no assurance that new product experiences, features, or capabilities will be released according to schedule. Any delays could result in adverse publicity, loss of revenue or market acceptance, or claims by users brought against us, all of which could have a material and adverse effect on our reputation, business, results of operations, and financial condition. Moreover, new features may require substantial investment, and we have no assurance that such investments will be successful. If users do not widely adopt our new product experiences, features, and capabilities, we may not be able to realize a return on our investment. If we are unable to develop, license, or acquire new features and capabilities to our platform on a timely and cost-effective basis, or if such enhancements do not achieve market acceptance, our business, results of operations, and financial condition could be adversely affected.

The full extent of the impacts of the COVID-19 pandemic on our business is currently unknown, but it may adversely affect our financial results as well as our business operations.

Although we did not experience material impacts to our financial condition and results of operations during the three months ended March 31, 2022, as a result of the on-going COVID-19 pandemic, the full extent of the impacts of the COVID-19 pandemic on our financial results and business operations are currently unknown and cannot be estimated with any degree of certainty. Impacts to our financial results may include, without limitation, (1) negative impacts to our current and prospective users’ purchases or renewals of paid licenses for access to our platform, delays or defaults on payment obligations, which could negatively affect our revenues and cash flows, (2) modifications to net payment terms or invoice frequency, which could negatively affect our cash flows, and (3) fluctuations in foreign currency exchange rates, which have and may in the future negatively impact our results of operations and cash flows. Impacts to our business operations may include, without limitation, (1) disruptions to our sales operations and marketing efforts, (2) negative impacts to the financial condition or operations of our vendors and business partners, as well as disruptions to the supply chain of hardware needed to offer our services, (3) disruptions to our ability to conduct product development and other important business activities, and (4) potential postponement or cancellation of previously planned investments or other initiatives. In addition, economic effects related to the COVID-19 pandemic, such as ongoing supply chain disruption, a competitive labor market and labor shortages have impacted, and may continue to impact, us and our customers and vendors. Accordingly, the COVID-19 pandemic may have a negative impact on our financial results as well as our business operations, the magnitude and duration of which we are currently unable to predict. Additionally, concerns over the economic impact of the COVID-19 pandemic have caused extreme volatility in financial and other capital markets which may adversely impact our stock price.

We have seen, and expect to continue to see, cost savings from the shift to remote work for all of our employees as a result of the COVID-19 pandemic in areas that include events, travel, utilities, and other benefits. Although we anticipate that some of these cost savings will continue beyond the resolution of the COVID-19 pandemic as result of our continuing shift to a Virtual First work model, we expect that some expenses in these areas will increase relative to current levels as we become more able to offer our employees opportunities for in-person collaboration, and this may impact our rate of profitability in future periods.

We may not successfully manage our growth or successfully execute our plan for future growth.

~~Since our founding in 2007, we have experienced rapid growth.~~ The growth and expansion of our business, including the introduction of new features and products, places a continuous significant strain on our management, operational, and financial resources. As we introduce new products and features, and our user base and third-party relationships expand, our information technology systems, organizational structures, and internal controls and procedures may not be adequate to support our operations. In addition, we face challenges of integrating, developing, and motivating an increasingly distributed employee base in various countries around the world. These challenges may be heightened ~~as we~~in connection with our transition to a Virtual First workforce and seek to align our resources in order to create a more nimble and streamlined organization. Certain members of our management ~~have not previously worked together for an extended period of time and some~~ do not have prior experience

Table of Contents

managing a public company, which may affect how they manage our growth. Managing our growth will also require significant expenditures and allocation of valuable management resources.

In addition, the expansion of our business may make it difficult to evaluate our future prospects. Our ability to forecast our future results of operations is subject to a number of uncertainties, including our ability to effectively plan for and model future growth. We have encountered in the past, and may encounter in the future, risks and uncertainties frequently experienced by growing companies in rapidly changing industries. If we fail to achieve the necessary level of efficiency in our organization as it grows, or if we are not able to accurately forecast future growth, our business, results of operations, and financial condition could be harmed.

We depend on our key personnel and other highly qualified personnel, and if we fail to attract, integrate, and retain our personnel, and maintain our unique corporate culture, our business could be harmed.

We depend on the continued service and performance of our key personnel. In particular, Andrew W. Houston, our Chief Executive Officer and one of our co-founders, is critical to our vision, strategic direction, culture, and offerings. From time to time, there have been changes in our management team resulting from the hiring or departure of our executives, and there may be additional changes in the future. While we seek to manage these transitions carefully, such changes may result in a loss of institutional knowledge and may cause disruptions to our business. If we fail to successfully integrate new key personnel into our organization or if key employees are unable to successfully transition into new roles, our business could be adversely affected.

All of our officers and key personnel are at-will employees. In addition, many of our key technologies and systems are custom-made for our business by our key personnel. The loss of key personnel, including key members of our management team, as well as certain of our key marketing, sales, product development, or technology personnel, could disrupt our operations and have an adverse effect on our ability to grow our business. In addition, while we believe our ~~new~~ Virtual First strategy will give us the opportunity to realign our resources in order to create a more nimble and streamlined organization, we can provide no assurance that we will be able to successfully execute on these plans, and failure to successfully manage these transitions may cause disruptions to our business. Additionally, we will need to adapt and respond to frequently changing circumstances that may impact our workforce, such as natural disasters or pandemics (including the ongoing COVID-19 pandemic), or our ability to maintain an effective workforce may be impacted.

To execute our business plan, we must attract and retain highly qualified personnel. Competition for these employees is intense and has recently intensified as a result of industry trends and we may not be successful in attracting and retaining qualified personnel. We have experienced, and we may continue experience, difficulty in hiring and retaining highly skilled employees with appropriate qualifications. As we transition to a Virtual First workforce, our recent hires and planned hires may

~~Table of Contents~~

not become as productive as we expect, and we may be unable to hire, integrate, or retain sufficient numbers of qualified individuals. Many of the companies with which we compete for experienced personnel have greater resources than we have. In addition, in making employment decisions, particularly in the internet and high-technology industries, job candidates often consider the value of the equity they are to receive in connection with their employment. Employees may be more likely to leave us if the shares they own or the shares underlying their equity incentive awards have significantly appreciated or significantly reduced in value. Many of our employees may receive significant proceeds from sales of our equity in the public markets, which may reduce their motivation to continue to work for us. Furthermore, our workforce reduction in January 2021 may result in increased attrition beyond our intended reduction-in-force, reduce employee morale and negatively impact employee recruiting and retention. If we fail to attract new personnel, or fail to retain and motivate our current personnel, our business and growth prospects could be harmed.

Additionally, if we do not maintain and continue to develop our corporate culture as we grow and evolve, it could harm our ability to foster the innovation, creativity, and teamwork we believe that we need to support our growth. Additions of executive-level management, significant numbers of new and remote employees, ~~our workforce reduction~~ and higher employee turnover could significantly and adversely impact our culture, as could our transition to a Virtual First workforce.

Our lack of a significant outbound sales force may limit the potential growth of our business.

Historically, our business model has been driven by organic adoption and viral growth, with more than 90% of our revenue generated from self-serve channels. As a result, we do not have a significant outbound sales force, which has enabled us to be more efficient with our sales and marketing spend. Furthermore, as part of our workforce reduction in January 2021 we have reduced the size of our outbound sales force to simplify and drive further efficiencies in our outbound sales operations. Although we believe our business model can continue to scale without a large outbound sales force, our word-of-mouth and user referral marketing model may not continue to be as successful as we anticipate, and our limited experience selling directly to large organizations through our outbound sales force may impede our future growth. As we continue to scale our business, an enhanced sales infrastructure could assist in reaching larger organizations and growing our revenue. Identifying and recruiting

Table of Contents

additional qualified sales personnel and training them would require significant time, expense, and attention, and would significantly impact our business model. Further, adding more sales personnel would change our cost structure and results of operations, and we may have to reduce other expenses in order to accommodate a corresponding increase in sales and marketing expenses. If our limited outbound sales force and lack of experience selling and marketing to large organizations prevents us from reaching larger organizations and growing our revenue, and if we are unable to hire, develop, and retain talented sales personnel in the future, our business, results of operations, and financial condition could be adversely affected.

We may expand sales to large organizations, which could lengthen sales cycles and result in greater deployment challenges.

As our business evolves, we may need to invest more resources into sales to large organizations. Large organizations may undertake a significant evaluation and negotiation process, which can lengthen our sales cycle. We may also face unexpected deployment challenges with large organizations or more complicated deployment of our platform. Large organizations may demand more configuration and integration of our platform or require additional security management or control features. We may spend substantial time, effort, and money on sales efforts to large organizations without any assurance that our efforts will produce any sales. Additionally, our ability to sell via an outbound sales force has been, and may continue to be, impeded by catastrophic events, including public health epidemics such as the ongoing COVID-19 pandemic, that limit our ability to travel or meet in person, as well as the reduction in the size of our outbound sales force as part of our workforce reduction in January 2021. As a result, sales to large organizations may lead to greater unpredictability in our business, results of operations, and financial condition.

Any failure to offer high-quality customer support may harm our relationships with our users and our financial results.

We have designed our platform to be easy to adopt and use with minimal to no support necessary. Any increased user demand for customer support could increase costs and harm our results of operations. In addition, as we continue to grow our operations and support our global user base, we need to be able to continue to provide efficient customer support that meets our customers’ needs globally at scale. Paying users receive additional customer support features and the number of our paying users has grown significantly, which will put additional pressure on our support organization. For example, the number of paying users has grown from 8.81 million as of December 31, 2016, to ~~16.49~~17.09 million as of ~~September 30, 2021.~~March 31, 2022. If we are unable to provide efficient customer support globally at scale, our ability to grow our operations may be harmed and we may need to hire additional support personnel, which could harm our results of operations. Our new user signups are highly dependent on our business reputation and on positive recommendations from our existing users. Any failure to maintain high-quality customer support, or a market perception that we do not maintain high-quality customer support, could harm our reputation, business, results of operations, and financial condition.

~~Table of Contents~~

Our business depends on a strong brand, and if we are ~~not able~~unable to maintain and enhance our brand, our ability to expand our base of users will be impaired and our business, results of operations, and financial condition will be harmed.

We believe that our brand identity and awareness have contributed to our success and have helped fuel our efficient go-to-market strategy. We also believe that maintaining and enhancing the Dropbox brand is critical to expanding our base of users. We anticipate that, as our market becomes increasingly competitive, maintaining and enhancing our brand may become increasingly difficult and expensive. Any unfavorable publicity or consumer perception of our platform or the providers of content collaboration solutions generally could adversely affect our reputation and our ability to attract and retain users. Additionally, if we fail to promote and maintain the Dropbox brand, our business, results of operations, and financial condition will be materially and adversely affected.

We are continuing to expand our operations outside the United States, where we may be subject to increased business and economic risks that could impact our results of operations.

We have paying users across 180 countries and approximately half of our revenue in the year ended December 31, ~~2020~~2021 was generated from paying users outside the United States. We expect to continue to expand our international operations, which may include employees working in new jurisdictions and providing our platform in additional languages. Any new markets or countries into which we attempt to sell subscriptions to our platform may not be receptive. For example, we may not be able to expand further in some markets if we are ~~not able~~unable to satisfy certain government- and industry-specific requirements. In addition, our ability to manage our business and conduct our operations internationally requires considerable management attention and resources and is subject to the particular challenges of supporting a rapidly growing business in an environment of multiple languages, cultures, customs, legal and regulatory systems, alternative dispute systems, and commercial markets. International expansion has required, and will continue to require, investment of significant funds and other resources. Operating internationally subjects us to new risks and may increase risks that we currently face, including risks associated with:

Table of Contents

•compliance with applicable international laws, regulations, and standards including laws and regulations with respect to privacy, data protection, consumer protection, and unsolicited email, and the risk of penalties to our users and individual members of management or employees if our practices are deemed to be out of compliance;

•recruiting and retaining talented and capable employees outside the United States, and maintaining our company culture across all of our locations, including as we shift to Virtual First and an increasingly distributed workforce;

•providing our platform and operating our business across a significant distance, in different languages and among different cultures, including the potential need to modify our platform and features to ensure that they are culturally appropriate and relevant in different countries;

•management of an employee base in jurisdictions that may not give us the same employment and retention flexibility as does the United States;

•operating in jurisdictions that do not protect intellectual property rights to the same extent as does the United States;

•compliance by us and our business partners with anti-corruption laws, import and export control laws, tariffs, trade barriers, economic sanctions, and other regulatory limitations on our ability to provide our platform in certain international markets;

•foreign exchange controls that might require significant lead time in setting up operations in certain geographic territories and might prevent us from repatriating cash earned outside the United States;

•political and economic ~~instability;~~instability, such as the conflict between Russia and Ukraine and its regional and global ramifications;

•changes in diplomatic and trade relationships, including the imposition of new trade restrictions, trade protection measures, import or export requirements, trade embargoes and other trade barriers;

•double taxation of our international earnings and potentially adverse tax consequences due to changes in the income and other tax laws of the United States or the international jurisdictions in which we operate;

~~Table of Contents~~

•higher costs of doing business internationally, including increased accounting, travel, infrastructure, and legal compliance costs; and

•the impact of natural disasters and public health epidemics on employees, travel and the global economy, including the ongoing global COVID-19 pandemic.

Compliance with laws, regulations, and standards applicable to our global operations substantially increases our cost of doing business in international jurisdictions. We may be unable to keep current with changes in laws, regulations, or standards as they change. Although we have implemented policies and procedures designed to support compliance with these laws, regulations, and standards there can be no assurance that we will always maintain compliance or that all of our employees, contractors, partners, and agents will comply. Any violations could result in regulatory investigations and enforcement actions, fines, civil and criminal penalties, damages, injunctions, restrictions on our ability to conduct business, or reputational harm. If we are unable comply with these laws and regulations or manage the complexity of our global operations successfully, our business, results of operations, and financial condition could be adversely affected.

We depend on our infrastructure and third-party datacenters, and any disruption in the operation of these facilities or failure to renew the services could adversely affect our business.

We host our services and serve all of our users using a combination of our own custom-built infrastructure that we lease and operate in co-location facilities and third-party datacenter services such as Amazon Web Services. While we typically control and have access to the servers we operate in co-location facilities and the components of our custom-built infrastructure that are located in those co-location facilities, we control neither the operation of these facilities nor our third-party service providers. Furthermore, we have no physical access or control over the services provided by Amazon Web Services.

Table of Contents

Datacenter leases and agreements with the providers of datacenter services expire at various times. The owners of these datacenters and providers of these datacenter services may have no obligation to renew their agreements with us on commercially reasonable terms, or at all. Problems faced by datacenters, with our third-party datacenter service providers, with the telecommunications network providers with whom we or they contract, or with the systems by which our telecommunications providers allocate capacity among their users, including us, could adversely affect the experience of our users or result in unexpected increases in our costs. Our third-party datacenter operators could decide to close their facilities or cease providing services without adequate notice. In addition, any financial difficulties, such as bankruptcy, faced by our third-party datacenter operators or any of the service providers with whom we or they contract may have negative effects on our business, the nature and extent of which are difficult to predict.

If the datacenters and service providers that we use are unable to keep up with our growing needs for capacity, or if we are unable to renew our agreements with datacenters, and service providers on commercially reasonable terms, we may be required to transfer servers or content to new datacenters or engage new service providers, and we may incur significant costs, and possible service interruption in connection with doing so. Any changes in third-party service levels at datacenters or any real or perceived errors, defects, disruptions, or other performance problems with our platform could harm our reputation and may result in damage to, or loss or compromise of, our users’ content. Interruptions in our platform might, among other things, reduce our revenue, cause us to issue refunds to users, subject us to potential liability, harm our reputation, or decrease our renewal rates.

We have relationships with third parties to provide, develop, and create applications that integrate with our platform, and our business could be harmed if we are ~~not able~~unable to continue these relationships.

We use software and services licensed and procured from third parties to develop and offer our platform. We may need to obtain future licenses and services from third parties to use intellectual property and technology associated with the development of our platform, which might not be available to us on acceptable terms, or at all. Any loss of the right to use any software or services required for the development and maintenance of our platform could result in delays in the provision of our platform until equivalent technology is either developed by us, or, if available from others, is identified, obtained, and integrated, which could harm our platform and business. Any errors or defects in third-party software or services could result in errors or a failure of our platform, which could harm our business, results of operations, and financial condition.

We also depend on our ecosystem of developers to create applications that will integrate with our platform. As of December 31, ~~2020,~~2021, Dropbox was receiving over 6075 billion API calls per month, and ~~more than 750,000~~just under 1,000,000 developers had registered and built applications on our platform. Our reliance on this ecosystem of developers creates certain business risks

~~Table of Contents~~

relating to the quality of the applications built using our APIs, service interruptions of our platform from these applications, lack of service support for these applications, and possession of intellectual property rights associated with these applications.

We may not have the ability to control or prevent these risks. As a result, issues relating to these applications could adversely affect our business, brand, and reputation.

Our use of open source software could negatively affect our ability to offer and sell subscriptions to our platform and subject us to possible litigation.

A portion of the technologies we use incorporates open source software, and we may incorporate open source software in the future. Open source software is generally licensed by its authors or other third parties under open source licenses. These licenses may subject us to certain unfavorable conditions, including requirements that we offer our platform that incorporates the open source software for no cost, that we make publicly available source code for modifications or derivative works we create based upon, incorporating or using the open source software, or that we license such modifications or derivative works under the terms of the particular open source license. Additionally, if a third-party software provider has incorporated open source software into software that we license from such provider, we could be required to disclose any of our source code that incorporates or is a modification of our licensed software. If an author or other third party that distributes open source software that we use or license were to allege that we had not complied with the conditions of the applicable license, we could be required to incur significant legal expenses defending against those allegations and could be subject to significant damages, enjoined from offering or selling our solutions that contained the open source software, and required to comply with the foregoing conditions. Any of the foregoing could disrupt and harm our business, results of operations, and financial condition.

Our ability to sell subscriptions to our platform could be harmed by real or perceived material defects or errors in our platform.

Table of Contents

The software technology underlying our platform is inherently complex and may contain material defects or errors, particularly when first introduced or when new features or capabilities are released. We have from time to time found defects or errors in our platform, and new defects or errors in our existing platform or new software may be detected in the future by us or our users. There can be no assurance that our existing platform and new software will not contain defects. Any real or perceived errors, failures, vulnerabilities, or bugs in our platform could result in negative publicity or lead to data security, access, retention, or other performance issues, all of which could harm our business. The costs incurred in correcting such defects or errors may be substantial and could harm our results of operations and financial condition. Moreover, the harm to our reputation and legal liability related to such defects or errors may be substantial and could harm our business, results of operations, and financial condition.

We also utilize hardware purchased or leased and software and services licensed from third parties on our platform. Any defects in, or unavailability of, our or third-party software, services, or hardware that cause interruptions to the availability of our services, loss of data, or performance issues could, among other things:

•cause a reduction in revenue or delay in market acceptance of our platform;

•require us to issue refunds to our users or expose us to claims for damages;

•cause us to lose existing users and make it more difficult to attract new users;

•divert our development resources or require us to make extensive changes to our platform, which would increase our expenses;

•increase our technical support costs; and

•harm our reputation and brand.

We have acquired, and may in the future acquire, other businesses, and we may also receive offers to be acquired, any of which could require significant management attention, disrupt our business, or dilute stockholder value.

As part of our business strategy, we have acquired, and may in the future acquire, other companies, employee teams, or technologies to complement or expand our products, obtain personnel, or otherwise grow our business. For example, in the first fiscal quarter of 2021, we acquired DocSend, a secure document sharing platform, to expand our content collaboration capabilities to include additional business critical workflows. Additionally, in the fourth fiscal quarter of 2021, we acquired Command E, a universal search and productivity company, to enhance our search capability. The pursuit of acquisitions may divert the attention of

~~Table of Contents~~

management and cause us to incur various expenses in identifying, investigating, and pursuing suitable acquisitions, whether or not they are consummated.

We have limited experience making acquisitions. We may not be able to find suitable acquisition candidates and we may not be able to complete acquisitions on favorable terms, if at all, and even if we are able to identify suitable acquisition candidates, we may not be able to receive approval from the applicable competition authorities, or such target may be acquired by another company, including one of our ~~competitors~~.competitors. If we do complete acquisitions, we may not ultimately strengthen our competitive position or achieve the anticipated benefits from such acquisitions, due to a number of factors, including:

•acquisition-related costs, liabilities, or tax impacts, some of which may be unanticipated;

•difficulty integrating and retaining the personnel, intellectual property, technology infrastructure, and operations of an acquired business;

•ineffective or inadequate, controls, procedures, or policies at an acquired business;

•multiple product lines or services offerings, as a result of our acquisitions, that are offered, priced, and supported differently;

•potential unknown liabilities or risks associated with an acquired business, including those arising from existing contractual obligations or litigation matters;

•inability to maintain relationships with key customers, suppliers, and partners of an acquired business;

Table of Contents

•lack of experience in new markets, products or technologies;

•diversion of management's attention from other business concerns; and

•use of resources that are needed in other parts of our business.

In addition, a significant portion of the purchase price of companies we acquire may be allocated to acquired goodwill. We review goodwill for impairment at least annually. In the future, if our acquisitions do not yield expected returns, we may be required to record impairment charges based this assessment, which could adversely affect our results of operations.

We may not be able to integrate acquired businesses successfully or effectively manage the combined company following an acquisition. If we fail to successfully integrate acquisitions, or the people or technologies associated with those acquisitions, the results of operations of the combined company could be adversely affected. Any integration process will require significant time, resources, and attention from management, and disrupt the ordinary functioning of our business, and we may not be able to manage the process successfully, which could adversely affect our business, results of operations, and financial condition.

Any acquisition we complete could be viewed negatively by users, developers, partners, or investors, and could have adverse effects on our existing business relationships. In addition, we may not successfully evaluate or utilize acquired technology or accurately forecast the financial impact of an acquisition transaction, including accounting charges.

We may have to pay a substantial portion of our available cash, incur debt, or issue equity securities to pay for any such acquisitions, each of which could affect our financial condition or the value of our capital stock. The sale of equity to finance any such acquisitions could result in dilution to our stockholders. If we incur more debt, it would result in increased fixed obligations and could also subject us to covenants or other restrictions that would impede our ability to flexibly operate our business.

Our business may be significantly impacted by a change in ~~the economy,~~general economic, political, and market conditions, including any resulting effect on consumer or business spending.

Our business may be affected by ~~changes in the economy generally,~~general economic, political, and market conditions, including any resulting effect on spending by our business and consumer users. Some of our users may view a subscription to our platform as a discretionary purchase, and our paying users may reduce their discretionary spending on our platform during an economic ~~downturn. If an economic~~ downturn, ~~were to occur, we may experience such a reduction in the future,~~ especially in the event of a prolonged recessionary period. ~~For example,~~Concerns about inflation, geopolitical issues, such as the conflict between Russia and Ukraine, the ongoing COVID-19 pandemic ~~and efforts to control such pandemic have resulted in~~or a widespread economic ~~uncertainty worldwide and may cause, or have already caused, an economic recession in~~slowdown (in the United States or internationally) have and ~~elsewhere,~~could continue to lead to increased market volatility and economic uncertainty, which could

~~Table of Contents~~

cause current and prospective paying users to delay, decrease, or cancel purchases of our products and services, or delay or default on their payment obligations. As a result, our business, results of operations, and financial condition may be significantly affected by changes in the economy generally.

Our current and future indebtedness may limit our operating flexibility or otherwise affect our business.

Our current indebtedness, including our 2026 Notes, 2028 Notes and our revolving credit facility, place significant restrictions on our business and could have important consequences to our stockholders and effects on our business, as could any future indebtedness.

For example, the terms of our revolving credit and guarantee agreement, as amended, contain a number of covenants that limit our ability and our subsidiaries’ ability to, among other things, incur additional indebtedness, pay dividends, make redemptions and repurchases of stock, make investments, loans and acquisitions, create liens, engage in transactions with affiliates, merge or consolidate with other companies, or sell substantially all of our assets. We are also required to maintain certain financial covenants, including a consolidated leverage ratio incurrence covenant and a minimum liquidity balance.

In addition, such current and future indebtedness could:

•make it more difficult for us to satisfy our debt obligations, including the 2026 Notes and the 2028 Notes;

•increase our vulnerability to general adverse economic and industry conditions;

Table of Contents

•require us to dedicate a substantial portion of our cash flow from operations to payments on our indebtedness, thereby reducing the availability of our cash flow to fund working capital and other general corporate purposes;

•limit our flexibility in planning for, or reacting to, changes in our business and the industry in which we operate;

•restrict our current and future operations, make it more difficult to successfully execute our business strategy, or restrict us from exploiting business opportunities;

•place us at a competitive disadvantage compared to our competitors that have less indebtedness or are not subject to restrictive covenants;

•restrict or otherwise impact the pace and timing of repurchases under our stock repurchase program; and

•limit our availability to borrow additional funds for working capital, capital expenditures, acquisitions, debt service requirements, execution of our business strategy, or other general purposes.

Any of the foregoing could have a material adverse effect on our business, cash flows, results of operations, and financial condition.

Our operations may be interrupted and our business, results of operations, and financial condition could be adversely affected if we default on our leasing or credit obligations.

We finance a significant portion of our expenditures through leasing arrangements, and we may enter into additional similar arrangements in the future. As of December 31, ~~2020,~~2021, we had an aggregate of ~~$1,624.1~~$1,342.0 million of commitments to settle contractual obligations. In particular, we utilize both finance and operating leases to finance some of our equipment, datacenters and offices. In addition, we may draw upon our revolving credit facility to finance our operations or for other corporate purposes. If we default on these leasing or credit obligations, our leasing partners and lenders may, among other things:

•require repayment of any outstanding lease obligations;

•terminate our leasing arrangements;

•terminate our access to the leased datacenters we utilize;

•stop delivery of ordered equipment;

•sell or require us to return our leased equipment;

~~Table of Contents~~

•require repayment of any outstanding amounts drawn on our revolving credit facility;

•terminate our revolving credit facility; or

•require us to pay significant fees, penalties, or damages.

If some or all of these events were to occur, our operations may be interrupted and our ability to fund our operations or obligations, as well as our business, results of operations, and financial condition, could be adversely affected. In particular, if the debt under our revolving credit facility were to be accelerated, we may not have sufficient cash or be able to borrow sufficient funds to refinance the debt or sell sufficient assets to repay the debt, which could immediately materially and adversely affect our business, cash flows, results of operations, and financial condition. Even if we were able to obtain new financing, it may not be on commercially reasonable terms or on terms that are acceptable to us.

Risks Related to Our Financial Performance or Results

Our revenue growth rate has declined in recent periods and may continue to slow in the future.

We have experienced significant revenue growth in prior periods. However, our rates of revenue growth have slowed and may continue to slow in future periods. Many factors may contribute to declines in our growth rates, including higher market

Table of Contents

penetration, increased competition, particularly from the availability of less expensive and bundled competitive products, slowing demand for our platform, a decrease in the growth of the overall content collaboration market, a failure by us to continue capitalizing on growth opportunities, the impact of catastrophic events on economic conditions or on our current and prospective paying users, and the maturation of our business, among others. You should not rely on the revenue growth of any prior quarterly or annual period as an indication of our future performance. If our growth rates decline further, investors’ perceptions of our business and the trading price of our Class A common stock could be adversely affected.

We have a history of net losses, we may increase expenses in the future, and we may not be able to achieve or maintain profitability.

We have incurred net losses on an annual basis since our inception. We incurred net losses of $256.3 million, $52.7 million, and $484.9 million in the years ended December 31, 2020, 2019, and 2018, respectively, and we had an accumulated deficit of $2,241.4 million as of December 31, 2020. While we have been profitable on a GAAP basis in prior fiscal quarters, ~~we have not been~~2021 was our first profitable ~~for a~~ full fiscal ~~year, and we~~year. We may, however, not achieve or maintain profitability in future periods. We incurred net losses on an annual basis from our inception until 2020. We incurred net losses of $256.3 million and $52.7 million in the years ended December 31, 2020 and 2019, respectively. We generated net income of $335.8 million in the year ended December 31, 2021 and we had an accumulated deficit of $2,739.4 million as of December 31, 2021. As we strive to grow our business, expenses may increase, particularly as we continue to make investments to scale our business. For example, we will need an increasing amount of technical infrastructure to continue to satisfy the needs of our user base. Our research and development expenses may also increase as we plan to continue to hire employees for our engineering, product, and design teams to support these efforts. These investments may not result in increased revenue or growth in our business or our revenue may not grow to the extent we expect and expense growth may outpace revenue. Further, we have created mobile applications and mobile versions of Dropbox that are distributed to users primarily through app stores operated by Apple and Google, each of whom charge us in-application purchase fees. As a result, if more of our users subscribe to our products through mobile applications, these fees may have an adverse impact on our results of operations. In addition, although we anticipate that our shift to a ~~new~~ Virtual First work model will have a long-term positive impact on our financial results and business operations, the impact remains uncertain. We have incurred impairment charges related to our facilities and may incur additional or unanticipated expense related to subleasing our facilities, including lower than anticipated sublease income that may result in additional or higher impairment charges than we have currently estimated, particularly if we are unable to sublease our unused office space on favorable terms or at all or if our subtenants fail to make lease payments to us in connection with our shift to a Virtual First model. We may also encounter unforeseen or unpredictable factors, including unforeseen operating expenses, complications, or delays, which may result in increased costs, or cause us to generate less sublease income than we have currently estimated. Furthermore, it is difficult to predict the size and growth rate of our market, user demand for our platform or for any new features or products we develop, user adoption and renewal of our platform or of any new features or products we develop, the entry of competitive products and services, or the success of existing competitive products and services. As a result, we may not achieve or maintain profitability in future periods. If we fail to grow our revenue sufficiently to keep pace with our investments and other expenses, our results of operations and financial condition would be adversely affected.

~~Table of Contents~~

Servicing our 2026 Notes and 2028 Notes may require a significant amount of cash, and we may not have sufficient cash flow or the ability to raise the funds necessary to satisfy our obligations under the 2026 Notes or 2028 Notes.

Our ability to make scheduled payments of the principal of, to pay interest on or to refinance our indebtedness, including the 2026 Notes and 2028 Notes, or to make cash payments in connection with any conversion of the 2026 Notes, 2028 Notes or upon any fundamental change if holders of the applicable series of notes require us to repurchase their notes for cash, depends on our future performance, which is subject to economic, financial, competitive and other factors beyond our control. Our business may not generate cash flow from operations in the future sufficient to service our indebtedness and make necessary capital expenditures. If we are unable to generate such cash flow, we may be required to adopt one or more alternatives, such as selling assets, restructuring indebtedness or obtaining additional equity capital on terms that may be onerous or highly dilutive. Our ability to refinance our indebtedness will depend on the capital markets and our financial condition at such time. We may not be able to engage in any of these activities or engage in these activities on desirable terms, which could result in a default on our debt obligations, which would materially and adversely impact our business, financial condition and operating results.

Our quarterly results may fluctuate significantly and may not fully reflect the underlying performance of our business.

Our quarterly results of operations, including our revenue, gross margin, operating margin, profitability, cash flow from operations, and deferred revenue, may vary significantly in the future and period-to-period comparisons of our results of operations may not be meaningful. Accordingly, the results of any one quarter should not be relied upon as an indication of future performance. For example, while we have been profitable on a GAAP basis in prior fiscal quarters, our quarterly operating results have fluctuated in the past and will fluctuate in the future. Our quarterly results of operations may fluctuate as a result of a variety of factors, many of which are outside of our control, and as a result, may not fully reflect the underlying

Table of Contents

performance of our business. Fluctuation in quarterly results may negatively impact the value of our securities. Factors that may cause fluctuations in our quarterly results of operations include, without limitation, those listed below:

•our ability to retain and upgrade paying users;

•our ability to attract new paying users and convert registered to paying users;

•the timing of expenses and recognition of revenue;

•the amount and timing of operating expenses related to the maintenance and expansion of our business, operations, and infrastructure, as well as entry into operating and finance leases;

•the timing of expenses related to acquisitions;

•any large indemnification payments to our users or other third parties;

•changes in our pricing policies or those of our competitors;

•the timing and success of new product feature and service introductions by us or our competitors;

•network outages or actual or perceived security breaches;

•changes in the competitive dynamics of our industry, including consolidation among competitors;

•changes in laws and regulations that impact our business;

•general economic and market conditions;

•catastrophic events, including earthquakes, fires, floods, tsunamis, or other weather events, power loss, telecommunications failures, software or hardware malfunctions, cyber-attack, war, or terrorist attacks, and pandemics such as the ongoing COVID-19 pandemic;

•changes in reserves or other non-cash credits or charges, such as the impairment charges related to certain of our unused office space in connection with our shift to a ~~new~~ Virtual First work model and releases of deferred tax asset valuation allowances; and

•any other impacts of shifting our operations to a ~~new~~ Virtual First work model.

~~Table of Contents~~

Our results of operations may not immediately reflect downturns or upturns in sales because we recognize revenue from our users over the term of their subscriptions with us.

We recognize revenue from subscriptions to our platform over the terms of these subscriptions. Our subscription arrangements generally have monthly or annual contractual terms, and we also have a small percentage of multi-year contractual terms. Amounts that have been billed are initially recorded as deferred revenue until the revenue is recognized. As a result, a large portion of our revenue for each quarter reflects deferred revenue from subscriptions entered into during previous quarters, and downturns or upturns in subscription sales, or renewals and potential changes in our pricing policies may not be reflected in our results of operations until later periods. Our subscription model also makes it difficult for us to rapidly increase our revenue through additional sales in any period, as subscription revenue from new users is recognized over the applicable subscription term. By contrast, a significant majority of our costs are expensed as incurred, which occurs as soon as a user starts using our platform. As a result, an increase in users could result in our recognition of more costs than revenue in the earlier portion of the subscription term. We may not attain sufficient revenue to maintain positive cash flow from operations or achieve profitability in any given period.

Our results of operations, which are reported in U.S. dollars, could be adversely affected if currency exchange rates fluctuate substantially in the future.

We conduct our business across 180 countries around the world. As we continue to expand our international operations, we will become more exposed to the effects of fluctuations in currency exchange rates. This exposure is the result of selling in

Table of Contents

multiple currencies and operating in foreign countries where the functional currency is the local currency. In ~~2020, 29%~~2021, 30% of our sales were denominated in currencies other than U.S. dollars. Our expenses, by contrast, are primarily denominated in U.S. dollars. As a result, any increase in the value of the U.S. dollar against these foreign currencies, including those resulting from the impact of the COVID-19 pandemic, could cause our revenue to decline relative to our costs, thereby decreasing our gross margins. Our results of operations are primarily subject to fluctuations in the Euro and British pound sterling. Because we conduct business in currencies other than U.S. dollars, but report our results of operations in U.S. dollars, we also face translation exposure to fluctuations in currency exchange rates, which could hinder our ability to predict our future results and earnings and could materially impact our results of operations. We do not currently maintain a program to hedge exposures to non-U.S. dollar currencies.

We are subject to counterparty risk with respect to the convertible note hedge transactions.

In connection with the pricing of the 2026 Notes and 2028 Notes, we entered into convertible note hedge transactions with certain financial institutions or affiliates of financial institutions, which we refer to as the “option counterparties,” and we will be subject to the risk that one or more of such option counterparties may default under the convertible note hedge transactions. Our exposure to the credit risk of the option counterparties will not be secured by any collateral. If any option counterparty becomes subject to insolvency proceedings, we will become an unsecured creditor in those proceedings with a claim equal to our exposure at that time under the convertible note hedge transaction. Our exposure will depend on many factors but, generally, the increase in our exposure will be correlated to the increase in the market price of our Class A common stock and in the volatility of the market price of our Class A common stock. In addition, upon a default by the option counterparty, we may suffer adverse tax consequences and dilution with respect to our Class A common stock. We can provide no assurance as to the financial stability or viability of any option counterparty.

Our ability to use our net operating loss carryforwards and certain other tax attributes may be limited.

As of December 31, ~~2020,~~2021, we had ~~$697.7~~$623.8 million of federal, ~~$292.8~~$352.1 million of state, and ~~$430.5~~$310.1 million of foreign net operating loss carryforwards available to reduce future taxable income. Of our federal net operating loss carryforwards, ~~$71.8~~$5.1 million will begin to expire in 2032 and ~~$625.9~~$618.7 million will carryforward indefinitely, while state net operating losses begin to expire in 2029. As of December 31, ~~2020,~~2021, we had research credit carryforwards of ~~$207.9~~$246.1 million and ~~$113.8~~$130.0 million for federal and state income tax purposes. The federal credit ~~carryforward~~carryforwards will begin to expire in ~~2027.~~2031. The state research credits have no expiration date. ~~The Company~~We also had ~~$2.1~~$3.6 million of state enterprise zone credit carryforwards as of December 31, 2021, which will begin to expire in ~~2023. We also had $0.5~~2023 and $0.6 million of foreign tax credit carryforwards as of December 31, 2021, which will carryforward indefinitely. It is possible that we will not generate taxable income in time to use these net operating loss carryforwards before their expiration or at all. Under Sections 382 and 383 of the Internal Revenue Code of 1986, as amended, or the Code, if a corporation undergoes an “ownership change,” the corporation’s ability to use its pre-change net operating loss carryforwards and other pre-change attributes, such as research tax credits, to offset its post-change income may be limited. In general, an “ownership change” will occur if there is a cumulative change in our ownership by “5-percent stockholders” that exceeds 50 percentage points over a rolling three-year period. Similar rules and other limitations may apply under state tax laws. We have determined that we have experienced multiple ownership changes and, as a result, the annual utilization of our net operating loss carryforwards and other

~~Table of Contents~~

pre-change attributes will be subject to limitation. However, we do not expect that the annual limitations will significantly impact our ability to utilize our net operating loss or tax credit carryforwards prior to expiration.

Our operating results may be harmed if we are required to collect sales or other related taxes for our subscription services in jurisdictions where we have not historically done so.

We collect sales and value-added tax as part of our subscription agreements in a number of jurisdictions. One or more states or countries may seek to impose incremental or new sales, use, or other tax collection obligations on us, including for past sales by us or our resellers and other partners. A successful assertion by a state, country, or other jurisdiction that we should have been or should be collecting additional sales, use, or other taxes on our services could, among other things, result in substantial tax liabilities for past sales, create significant administrative burdens for us, discourage users from purchasing our platform, or otherwise harm our business, results of operations, and financial condition.

Our results of operations and financial condition could be materially affected by the enactment of legislation implementing changes in the U.S. or foreign taxation of international business activities or the adoption of other tax reform policies.

In March 2022, the Biden Administration’s budget for fiscal year 2023 was released. The budget includes, but is not limited to, the following tax proposals, (1) raising the corporate income tax rate to 28%, (2) repealing the Base Erosion and Anti-Abuse Tax (“BEAT”) and replacing it with a new undertaxed profits rule (“UTPR”) that is intended to be consistent with

Table of Contents

the UTPR described in the OECD Pillar Two Model Rules. If enacted, certain proposed changes could have an adverse impact on our business, results of operations, financial condition and cash flow.

In October 2021, an update to the Build Back Better Act (the “Bill”) was released. The Bill, as revised, includes, but is not limited to, (1) reducing benefits included in the Global Intangible Low-Taxed Income (“GILTI”) regime and Foreign-Derived Intangible Income (“FDII”) deductions, (2) amending the ~~Base Erosion and Anti-Abuse Tax (“BEAT”)~~BEAT tax rates from 10% up to 18% through 2025, and (3) delaying the capitalization of research expenditures ~~to take~~that took effect in 2022. If enacted, certain proposed changes could have an adverse impact on our business, results of operations, financial condition and cash flow.

On June 5, 2021 the G7 Finance Ministers announced an agreement in which the participating countries committed to new taxing rights that allow countries to reallocate some portion of profits of large multinational companies with global revenues exceeding EUR20 billion to markets where sales arise (“Pillar One”), as well as enact a global minimum tax rate of at least 15% for multinationals with global revenue exceeding EUR750 million (“Pillar Two”). The meeting marked an early test of whether the US position on the OECD's Inclusive Framework ~~(“OECD IF”)~~ “Taxation of the Digital Economy” project would provide momentum to finding a common base for agreement. On ~~October~~December 8, 2021, the OECD ~~announced~~released Pillar Two model rules for implementation of a 15% global minimum tax, after previously announcing in October 2021 that ~~136~~137 member jurisdictions have politically committed to the potential changes to the international corporate tax system.

~~In 2018, the~~ On March 14, 2022, OECD released technical commentary. The European Commission (“EC”) introduced proposals addressing taxation of digital businesses operating within the European Union (“EU”) but has not reached an agreement on a sales tax with a scope limited to digital advertising services. As a result, certain countries, including the UK, Italy and France, unilaterally moved to introduce their own digital service tax. In January 2021, the EC released an Inception Impact Assessment to inform stakeholders about proposed legislative changes to the taxation of the digital economy. It is intended that the new initiative will help mitigate potential distortions and fragmentation of tax rules arising in the EU single market by designing a single set of rules which is consistent with the Digital Services Act package and the EC's digital strategy. In June 2021, as part of the OECD-IF'stargeting Pillar Two ~~there was an agreement~~ to ~~support efforts through~~take effect from the ~~G20/OECD-IF and provide for appropriate coordination between the application~~beginning of ~~the new international tax rules and the removal of all digital services taxes, and other similar measures, on all companies.~~2024.

Due to the increasing focus by government taxing authorities on multinational companies, the tax laws of certain countries in which we do business could change on a prospective or retroactive basis, and any such changes could increase our liabilities for taxes, interest and penalties, lead to higher effective tax rates, and harm our cash flows, results of operations and financial condition.

We have publicly disclosed market opportunity estimates, growth forecasts, and key metrics, including the key metrics included in this Quarterly Report on Form 10-Q which could prove to be inaccurate, and any real or perceived inaccuracies may harm our reputation and negatively affect our business.

Market opportunity estimates and growth forecasts are subject to significant uncertainty and are based on assumptions and estimates that may not prove to be accurate. The estimates and forecasts we disclose relating to the size and expected growth of our target market may prove to be inaccurate. Even if the markets in which we compete meet the size estimates and growth we have forecasted, our business could fail to grow at similar rates, if at all. We also rely on assumptions and estimates to calculate certain of our key metrics, such as annual recurring revenue, paying users, average revenue per paying user and free cash flow. We regularly review and may adjust our processes for calculating our key metrics to improve their accuracy. Our key metrics may differ from estimates published by third parties or from similarly titled metrics of our competitors due to differences in methodology. We have found that aggregate user activity metrics are not leading indicators of revenue or conversion. For that reason, we do not comprehensively track user activity across the Dropbox platform for financial planning and forecasting

~~Table of Contents~~

purposes. If investors or analysts do not perceive our metrics to be accurate representations of our business, or if we discover material inaccuracies in our metrics, our reputation, business, results of operations, and financial condition would be harmed.

Risks Related to Legal and Regulatory Compliance

We are subject to a variety of U.S. and international laws that could subject us to claims, increase the cost of operations, or otherwise harm our business due to changes in the laws, changes in the interpretations of the laws, greater enforcement of the laws, or investigations into compliance with the laws.

We are subject to compliance with various laws, including those covering copyright, indecent content, child protection, consumer protection, and similar matters. There have been instances where improper or illegal content has been stored on our platform without our knowledge. As a service provider, we do not regularly monitor our platform to evaluate the legality of content stored on it. While to date we have not been subject to material legal or administrative actions as result of this content, the laws in this area are currently in a state of flux and vary widely between jurisdictions. Accordingly, it may be possible that in the future we and our competitors may be subject to legal actions, along with the users who uploaded such content. In addition, regardless of any legal liability we may face, our reputation could be harmed should there be an incident generating extensive negative publicity about the content stored on our platform. Such publicity could harm our business and results of operations.

We are also subject to consumer protection laws that may impact our sales and marketing efforts, including laws related to subscriptions, billing, and auto-renewal. These laws, as well as any changes in these laws, could adversely affect our self-serve model and make it more difficult for us to retain and upgrade paying users and attract new ones. Additionally, we have in the past, are currently, and may from time to time in the future become the subject of inquiries and other actions by regulatory

Table of Contents

authorities as a result of our business practices, including our policies and practices around subscriptions, billing, auto-renewal, ~~intermediate~~intermediary liability, privacy, and data protection. Consumer protection laws may be interpreted or applied by regulatory authorities in a manner that could require us to make changes to our operations or incur fines, penalties or settlement expenses, which may result in harm to our business, results of operations, and brand.

Our platform depends on the ability of our users to access the internet and our platform has been blocked or restricted in some countries for various reasons. For example, our platform is blocked in the People’s Republic of China. If we fail to anticipate developments in the law, or fail for any reason to comply with relevant law, our platform could be further blocked or restricted and we could be exposed to significant liability that could harm our business.

We are also subject to various U.S. and international anti-corruption laws, such as the U.S. Foreign Corrupt Practices Act, the U.K. Bribery Act, and Irish Criminal Justice (Corruption Offences) Act 2018, as well as other similar anti-bribery and anti-kickback laws and regulations. These laws and regulations generally prohibit companies and their employees and intermediaries from authorizing, offering, or providing improper payments or benefits to officials and other recipients for improper purposes. Although we take precautions to prevent violations of these laws, our exposure for violating these laws increases as we continue to expand our international presence and any failure to comply with such laws could harm our reputation and our business.

We are subject to export and import control laws and regulations that could impair our ability to compete in international markets or subject us to liability if we violate such laws and regulations.

We are subject to U.S. export controls and sanctions regulations that prohibit the shipment or provision of certain products and services to certain countries, governments, and persons targeted by U.S. sanctions. While we take precautions to prevent our products and services from being exported in violation of these laws, including implementing IP address blocking, we may have experienced violations in the past and we cannot guarantee that the precautions we take will prevent future violations of export control and sanctions laws. For example, in 2017, we discovered that our platform had been accessed by certain users in apparent violation of United States sanctions regulations. We filed an Initial Voluntary Self Disclosure in October 2017 with the Office of Foreign Assets Control, or OFAC, and a Final Voluntary Self Disclosure with OFAC in February 2018. In October 2018, OFAC notified us that it had completed its review of these matters and closed its review with the issuance of a Cautionary Letter. No monetary penalties were assessed with respect to the 2018 filing. If in the future we are found to be in violation of U.S. sanctions or export control laws, it could result in substantial fines and penalties for us and for the individuals working for us, particularly in light of warning letters we previously received from OFAC.

In addition, various countries regulate the import and export of certain encryption and other technology, including import and export permitting and licensing requirements, and have enacted laws that could limit our ability to distribute our products or could limit our users’ ability to access our platform in those countries. Changes in our platform or client-side software, or future changes in export and import regulations may prevent our users with international operations from deploying our platform

~~Table of Contents~~

globally or, in some cases, prevent the export or import of our platform to certain countries, governments, or persons altogether. Any change in export or import regulations, economic sanctions or related legislation, or change in the countries, governments, persons or technologies targeted by such regulations, could result in decreased use of our platform by, or in our decreased ability to export or sell subscriptions to our platform to, existing or potential users with international operations. Any decreased use of our platform or limitation on our ability to export or sell our products would likely adversely affect our business, results of operations, and financial results.

Our actual or perceived failure to comply with privacy, data protection, and information security laws, regulations, and obligations could harm our business.

We receive, store, process, and use personal information and other user content. There are numerous federal, state, local, and international laws and regulations regarding privacy, data protection, information security, and the storing, sharing, use, processing, transfer, disclosure, and protection of personal information and other content, the scope of which are changing, subject to differing interpretations, and may be inconsistent among countries, or conflict with other rules. We also post privacy policies and are subject to contractual obligations to third parties related to privacy, data protection, and information security. We strive to comply with applicable laws, regulations, policies, and other legal obligations relating to privacy, data protection, and information security to the extent possible. However, the regulatory framework for privacy and data protection worldwide is, and is likely to remain, uncertain for the foreseeable future, and it is possible that these or other actual or alleged obligations may be interpreted and applied in a manner that is inconsistent from one jurisdiction to another and may conflict with other rules or our practices.

We also expect that there will continue to be new laws, regulations, and industry standards concerning privacy, data protection, and information security proposed and enacted in various jurisdictions. For example, in May 2018, the General Data

Table of Contents

Protection Regulation, or GDPR, went into effect in the EU. The GDPR imposed more stringent data protection requirements and provides greater penalties for noncompliance than previous data protection laws.

Additionally, although we have self-certified under the U.S.-EU and U.S.-Swiss Privacy Shield Frameworks with regard to our transfer of certain personal data from the European Economic Area ("EEA") and Switzerland to the United States, on July 16, 2020, the Court of Justice of the European Union ("CJEU") invalidated Decision 2016/1250 on the adequacy of the protection provided by the U.S.-EU Privacy Shield Framework, and on September 8, 2020, the Swiss Federal Data Protection and Information Commissioner ~~has stated~~announced that it no longer considers the U.S.-Swiss Privacy Shield adequate for the purposes of transfers of personal data from Switzerland to the U.S. While we rely on additional legal mechanisms to transfer data from the EEA and Switzerland to the United States, there is some regulatory uncertainty surrounding the future of data transfers from these locations to the United States, and we are closely monitoring regulatory developments in this area. In its decision invalidating the U.S.-EU Privacy Shield Framework, the CJEU also imposed additional obligations on companies relying on standard contractual clauses approved by the European Commission (“SCCs”) to transfer personal data. The CJEU decision may result in European data protection regulators applying differing standards for, and requiring additional measures in connection with, transfers of personal data from the EEA and Switzerland to the United States. The European Commission issued revised SCCs in June 2021 that are required to be implemented. The revised SCCs and other developments relating to cross-border data transfer may require us to implement additional contractual and technical safeguards for any personal data transferred out of the EEA and Switzerland, which may increase our costs, lead to increased regulatory scrutiny or liability, necessitate additional contractual negotiations, and adversely impact our business, results of operations, and financial results.

Additionally, several states in the U.S. have begun enacting new data privacy laws.For example, the California Consumer Privacy Act of 2018 (the "CCPA"), which affords consumers expanded privacy protections, went into effect on January 1, 2020. However, certain aspects of the CCPA and its enforcement remain uncertain. Additionally, a new privacy law, the California Privacy Rights Act ("CPRA"), which will go into effect on January 1, 2023, significantly modified the CCPA, potentially resulting in further uncertainty and requiring us to incur additional costs and expenses. The effects of the CCPA and the CPRA remain far-reaching, and depending on final regulatory guidance and other related developments, potentially may require us to modify our data processing practices and policies and to incur substantial costs and expenses in an effort to comply. The enactment of the CCPA has prompted similar legislative developments in other states, such as Virginia, which in March 2021 enacted a Consumer Data Protection Act that will go into effect January 1, 2023, and Colorado, which in June 2021 enacted a Colorado Privacy Act that will go into effect July 1, 2023. Similar laws are being considered by other state legislatures. These developments create the potential for a patchwork of overlapping but different state laws. Similarly, a number of legislative proposals in the European Union, the United States, at both the federal and state level, as well as other jurisdictions could impose new obligations in areas affecting our business. In addition, some countries are considering or have passed legislation implementing data protection requirements or requiring local storage and processing of data, or similar requirements, that could increase the cost and complexity of delivering our services.

With laws and regulations such as the GDPR in the EU and the California Consumer Privacy Act in the U.S. imposing new and relatively burdensome obligations, and with substantial uncertainty over the interpretation and application of these and other laws and regulations, we may face challenges in addressing their requirements and making necessary changes to our policies and practices, and may incur significant costs and expenses in an effort to do so. Any failure or perceived failure by us to comply with our privacy policies, our privacy-related obligations to users or other third parties, or any of our other legal obligations relating to privacy, data protection, or information security may result in governmental investigations or enforcement actions, litigation, claims, or public statements against us by consumer advocacy groups or others, and could result in significant liability or cause our users to lose trust in us, which could have an adverse effect on our reputation and business.

~~Table of Contents~~

Furthermore, the costs of compliance with, and other burdens imposed by, the laws, regulations, and policies that are applicable to the businesses of our users may limit the adoption and use of, and reduce the overall demand for, our services. In addition to government regulation, self-regulatory standards, industry-specific regulations and other industry standards or requirements may legally or contractually apply to us or be argued to apply to us, or we may elect to comply with, or to facilitate our customers’ compliance with, such regulations, standards, requirements, or other actual or asserted obligations. If we are unable or are perceived to be unable to comply with any of these regulations, standards, requirements, or other actual or asserted obligations, if we are unable to maintain certifications or standards relevant to our customers, or if our customers are unable to obtain regulatory approval to use our services where required, our business may be harmed. In addition, an inability to satisfy the standards of certain government agencies that our customers may expect may have an adverse impact on our business and results.

Additionally, if third parties we work with, such as vendors or developers, violate applicable laws or regulations or our policies, such violations may also put our users’ content at risk and could in turn have an adverse effect on our business. Any significant change to applicable laws, regulations, or industry practices regarding the collection, use, retention, security, or disclosure of our users’ content, or regarding the manner in which the express or implied consent of users for the collection,

Table of Contents

use, retention, or disclosure of such content is obtained, could increase our costs and require us to modify our services and features, possibly in a material manner, which we may be unable to complete, and may limit our ability to store and process user data or develop new services and features.

Our business could be adversely impacted by changes in internet access for our users or laws specifically governing the internet.

Our platform depends on the quality of our users’ access to the internet. Certain features of our platform require significant bandwidth and fidelity to work effectively. Internet access is frequently provided by companies that have significant market power that could take actions that degrade, disrupt or increase the cost of user access to our platform, which would negatively impact our business. We could incur greater operating expenses and our user acquisition and retention could be negatively impacted if network operators:

•implement usage-based pricing;

•discount pricing for competitive products;

•otherwise materially change their pricing rates or schemes;

•charge us to deliver our traffic at certain levels or at all;

•throttle traffic based on its source or type;

•implement bandwidth caps or other usage restrictions; or

•otherwise try to monetize or control access to their ~~networks.~~networks

On June 11, 2018, the repeal of the Federal Communications Commission’s, or FCC, “net neutrality” rules took effect and returned to a “light-touch” regulatory framework. The prior rules were designed to ensure that all online content is treated the same by internet service providers and other companies that provide broadband services. Additionally, California and a number of other states are considering or have enacted legislation or executive actions that would regulate the conduct of broadband providers. We cannot predict whether the FCC order or state initiatives will be modified, overturned, or vacated by legal action of the court, federal legislation, or the FCC. With the repeal of net neutrality rules in effect, we could incur greater operating expenses, which could harm our results of operations. As the internet continues to experience growth in the number of users, frequency of use, and amount of data transmitted, the internet infrastructure that we and our users rely on may be unable to support the demands placed upon it. The failure of the internet infrastructure that we or our users rely on, even for a short period of time, could undermine our operations and harm our results of operations.

In addition, there are various laws and regulations that could impede the growth of the internet or other online services, and new laws and regulations may be adopted in the future. These laws and regulations could, in addition to limiting internet neutrality, involve taxation, tariffs, privacy, data protection, content, copyrights, distribution, electronic contracts and other communications, consumer protection, and the characteristics and quality of services, any of which could decrease the demand for, or the usage of, our platform. Legislators and regulators may make legal and regulatory changes, or interpret and apply existing laws, in ways that require us to incur substantial costs, expose us to unanticipated civil or criminal liability, or cause us to change our business practices. These changes or increased costs could materially harm our business, results of operations, and financial condition.

We are currently, and may be in the future, party to intellectual property rights claims and other litigation matters and, if resolved adversely, they could have a significant impact on our business, results of operations, or financial condition.

We own a large number of patents, copyrights, trademarks, domain names, and trade secrets and, from time to time, are subject to litigation based on allegations of infringement, misappropriation or other violations of intellectual property, or other

~~Table of Contents~~

rights. As we face increasing competition and gain an increasingly high profile, the possibility of intellectual property rights claims, commercial claims, and other assertions against us grows. We have in the past been, are currently, and may from time to time in the future become, a party to litigation and disputes related to our intellectual property, our business practices, transactions involving our securities and our platform. For example, we were recently subject to a number of putative class action lawsuits in state and federal court alleging federal securities law violations in connection with our IPO. Although the lawsuits in both the federal and state courts have since been dismissed, we may not be successful in an appeal proceeding or in winning dismissal of an amended complaint. The costs of supporting litigation and dispute resolution proceedings are

Table of Contents

considerable, and there can be no assurances that a favorable outcome will be obtained. Our business, results of operations, and financial condition could be materially and adversely affected by such costs and any unfavorable outcomes in current or future litigation. We may need to settle litigation and disputes on terms that are unfavorable to us, or we may be subject to an unfavorable judgment that may not be reversible upon appeal. The terms of any settlement or judgment may require us to cease some or all of our operations or pay substantial amounts to the other party. With respect to any intellectual property rights claim, we may have to seek a license to continue practices found to be in violation of third-party rights, which may not be available on reasonable terms and may significantly increase our operating expenses. A license to continue such practices may not be available to us at all, and we may be required to develop alternative non-infringing technology or practices or discontinue the practices. The development of alternative, non-infringing technology or practices could require significant effort and expense.

Our failure to protect our intellectual property rights and proprietary information could diminish our brand and other intangible assets.

We rely and expect to continue to rely on a combination of patents, patent licenses, trade secrets, domain name protections, trademarks, and copyright laws, as well as confidentiality and license agreements with our employees, consultants, and third parties, to protect our intellectual property and proprietary rights. In the United States and abroad, we have over ~~1,200~~1,400 issued patents and more than ~~450~~350 pending patent applications. However, third parties may knowingly or unknowingly infringe our proprietary rights, third parties may challenge our proprietary rights, pending and future patent, trademark, and copyright applications may not be approved, and we may not be able to prevent infringement without incurring substantial expense. We have also devoted substantial resources to the development of our proprietary technologies and related processes. In order to protect our proprietary technologies and processes, we rely in part on trade secret laws and confidentiality agreements with our employees, consultants, and third parties. These agreements may not effectively prevent disclosure of confidential information and may not provide an adequate remedy in the event of unauthorized disclosure of confidential information. In addition, others may independently discover our trade secrets, in which case we would not be able to assert trade secret rights, or develop similar technologies and processes. Further, laws in certain jurisdictions may afford little or no trade secret protection, and any changes in, or unexpected interpretations of, the intellectual property laws in any country in which we operate may compromise our ability to enforce our intellectual property rights. Costly and time-consuming litigation could be necessary to enforce and determine the scope of our proprietary rights. If the protection of our proprietary rights is inadequate to prevent use or appropriation by third parties, the value of our platform, brand, and other intangible assets may be diminished and competitors may be able to more effectively replicate our platform and its features. Any of these events could materially and adversely affect our business, results of operations, and financial condition.

Risks Related to Ownership of Our Class A Common Stock

The trading price of our Class A common stock may be volatile, and you could lose all or part of your investment.

The trading price of our Class A common stock may be volatile and could be subject to fluctuations in response to various factors, some of which are beyond our control. Factors that could cause fluctuations in the trading price of our Class A common stock include the following:

•price and volume fluctuations in the overall stock market from time to time;

•volatility in the trading prices and trading volumes of technology stocks;

•changes in operating performance and stock market valuations of other technology companies generally, or those in our industry in particular;

•sales of shares of our Class A common stock by us or our stockholders;

•failure of securities analysts to maintain coverage of us, changes in financial estimates by securities analysts who follow our company, or our failure to meet these estimates or the expectations of investors;

~~Table of Contents~~

•the financial projections we may provide to the public, any changes in those projections, or our failure to meet those projections;

•announcements by us or our competitors of new products, features, or services;

•the public’s reaction to our press releases, other public announcements, and filings with the SEC;

Table of Contents

•rumors and market speculation involving us or other companies in our industry;

•actual or anticipated changes in our results of operations or fluctuations in our results of operations;

•actual or anticipated changes in our key metrics;

•actual or anticipated developments in our business, our competitors’ businesses or the competitive landscape generally;

•actual or perceived breaches of, or failures related to, privacy, data protection or data security;

•litigation involving us, our industry, or both, or investigations by regulators into our operations or those of our competitors;

•developments or disputes concerning our intellectual property or other proprietary rights;

•announced or completed acquisitions of businesses, products, services, or technologies by us or our competitors;

•new laws or regulations or new interpretations of existing laws or regulations applicable to our business;

•changes in accounting standards, policies, guidelines, interpretations, or principles;

•any significant change in our management; and

•general economic conditions and slow or negative growth of our markets and catastrophic events, including earthquakes, fires, floods, tsunamis, or other weather events, power loss, telecommunications failures, software or hardware malfunctions, cyber-attack, war, such as the conflict between Russia and Ukraine, or terrorist attacks, and pandemics such as the ongoing COVID-19 pandemic.

In addition, in the past, following periods of volatility in the overall market and the market price of a particular company’s securities, securities class action litigation has often been instituted against these companies. For example, we were recently subject to a number of putative class action lawsuits in state and federal court alleging federal securities law violations in connection with our IPO. Although the lawsuits in both the federal and state courts have since been dismissed, we may not be successful in an appeal proceeding or in winning dismissal of an amended complaint. This recent litigation, and any securities litigation that may be instituted against us in the future, could result in substantial costs and a diversion of our management’s attention and resources.

The multi-class structure of our common stock has the effect of concentrating voting control with those stockholders who held our capital stock prior to the completion of our IPO, and it may depress the trading price of our Class A common stock.

Our Class A common stock has one vote per share, our Class B common stock has ten votes per share, and our Class C common stock has no voting rights, except as otherwise required by law. As of ~~September 30, 2021,~~March 31, 2022, our directors, executive officers and holders of more than 5% of our common stock, and their respective affiliates, held in the aggregate ~~78.1%~~79.0% of the voting power of our capital stock, with Mr. Houston holding approximately ~~72.2%~~73.3% of the voting power of our capital stock. We are including Mr. Houston's Co-Founder Grant in this calculation since the shares underlying such grant are legally issued and outstanding shares of our Class A common stock and Mr. Houston is able to vote these shares prior to their vesting. Because of the ten-to-one voting ratio between our Class B and Class A common stock, the holders of our Class B common stock collectively will continue to control a majority of the combined voting power of our common stock and therefore be able to control all matters submitted to our stockholders for approval so long as the shares of Class B common stock represent at least 9.1% of all outstanding shares of our Class A and Class B common stock. This concentrated control will limit or preclude other

~~Table of Contents~~

stockholders' ability to influence corporate matters for the foreseeable future, including the election of directors, amendments of our organizational documents, and any merger, consolidation, sale of all or substantially all of our assets, or other major corporate transaction requiring stockholder approval. In addition, this may prevent or discourage unsolicited acquisition proposals or offers for our capital stock that other stockholders may feel are in their best interests as one of our stockholders.

Future transfers or sales by holders of Class B common stock will generally result in those shares converting to Class A common stock, except for certain transfers described in our amended and restated certificate of incorporation, including

Table of Contents

transfers effected for estate planning purposes where sole dispositive power and exclusive voting control with respect to the shares of Class B common stock is retained by the transferring holder and transfers between our co-founders. In addition, each outstanding share of Class B common stock held by a stockholder who is a natural person, or held by the permitted entities or permitted transferees of such stockholder (as described in our amended and restated certificate of incorporation), will convert automatically into one share of Class A common stock upon the death of such natural person. In the event of Mr. Houston's death or permanent and total disability, shares of Class B common stock held by Mr. Houston, his permitted entities or permitted transferees will convert to Class A common stock, provided that the conversion will be deferred for nine months, or up to 18 months if approved by a majority of our independent directors, following his death or permanent and total disability. Transfers between our co-founders are permitted transfers and will not result in conversion of the shares of Class B common stock that are transferred; however, upon the death or total and permanent disability of the transferring co-founder, the transferred shares would convert to Class A common stock following the deferral period of nine months, or up to 18 months if approved by a majority of our independent directors. The conversion of Class B common stock to Class A common stock will have the effect, over time, of increasing the relative voting power of those individual holders of Class B common stock who retain their shares in the long term.

In addition, because our Class C common stock carries no voting rights (except as otherwise required by law), if we issue Class C common stock in the future, the holders of Class B common stock may be able to elect all of our directors and to determine the outcome of most matters submitted to a vote of our stockholders for a longer period of time than would be the case if we issued Class A common stock rather than Class C common stock in such transactions.

Additionally, in July 2017, FTSE Russell and Standard & Poor’s announced that they would cease to allow most newly public companies utilizing dual or multi-class capital structures to be included in their indices. Affected indices include the Russell 2000 and the S&P 500, S&P MidCap 400, and S&P SmallCap 600, which together make up the S&P Composite 1500. Although we have since met the requirements to be included, and are now included, in an FTSE Russell index, our multi-class capital structure still makes us ineligible for inclusion in any of the above listed S&P indices, and as a result, mutual funds, exchange-traded funds, and other investment vehicles that attempt to passively track these S&P indices will not be investing in our stock. It is as of yet unclear what effect, if any, these policies will have on the valuations of publicly traded companies excluded from one or more of these indices, but it is possible that they may depress these valuations compared to those of other similar companies that are included.

Substantial future sales could depress the market price of our Class A common stock.

The market price of our Class A common stock could decline as a result of a large number of sales of shares of such stock, and the perception that these sales could occur may also depress the market price of our Class A common stock.

In addition, we have filed registration statements to register shares reserved for future issuance under our equity compensation plans. As a result, subject to the satisfaction of applicable exercise periods, the shares issued upon exercise of outstanding stock options or upon settlement of outstanding RSU awards are available for immediate resale in the United States in the open market.

Sales of our shares may make it more difficult for us to sell equity securities in the future at a time and at a price that we deem appropriate. These sales also could cause the trading price of our Class A common stock to fall and make it more difficult for you to sell shares of our Class A common stock.

Transactions relating to our 2026 Notes and 2028 Notes may dilute the ownership interest of stockholders, or may otherwise depress the price of our common stock.

If the 2026 Notes or the 2028 Notes are converted by holders of such series, we have the ability under the applicable indenture to deliver cash, common stock, or any combination of cash or common stock, at our election upon conversion of the applicable series of convertible notes. If we elect to deliver common stock upon conversion of the 2026 Notes or the 2028 Notes, it would dilute the ownership interests of existing stockholders. Any sales in the public market of the Class A common stock issuable upon such conversion could adversely affect prevailing market prices of our Class A common stock. In addition,

~~Table of Contents~~

certain holders of the 2026 Notes or the 2028 Notes may engage in short selling to hedge their position in the convertible notes. Anticipated future conversions of the 2026 Notes or 2028 Notes into shares of our Class A common stock could depress the price of our Class A common stock.

Table of Contents

Delaware law and provisions in our restated certificate of incorporation and restated bylaws could make a merger, tender offer, or proxy contest difficult, thereby depressing the market price of our Class A common stock.

Our status as a Delaware corporation and the anti-takeover provisions of the Delaware General Corporation Law may discourage, delay, or prevent a change in control by prohibiting us from engaging in a business combination with an interested stockholder for a period of three years after the person becomes an interested stockholder, even if a change of control would be beneficial to our existing stockholders. In addition, our restated certificate of incorporation and restated bylaws contain provisions that may make the acquisition of our company more difficult, including the following:

•any transaction that would result in a change in control of our company requires the approval of a majority of our outstanding Class B common stock voting as a separate class;

•our multi-class common stock structure, which provides our holders of Class B common stock with the ability to significantly influence the outcome of matters requiring stockholder approval, even if they own significantly less than a majority of the shares of our outstanding Class A common stock, Class B common stock, and Class C common stock;

•when the outstanding shares of Class B common stock represent less than a majority of the total combined voting power of our Class A and Class B common stock, or the Voting Threshold Date, our Board of Directors will be classified into three classes of directors with staggered three-year terms, and directors will only be able to be removed from office for cause;

•until the Class B common stock, as a class, converts to Class A common stock, any amendments to our restated certificate of incorporation will require the approval of two-thirds of the combined vote of our then-outstanding shares of Class A common stock and Class B common stock; and following the conversion of our Class B common stock, as a class, to Class A common stock, certain amendments to our amended and restated certificate of incorporation will require the approval of two-thirds of our then outstanding voting power;

•our amended and restated bylaws will provide that approval of stockholders holding two-thirds of our outstanding voting power voting as a single class is required for stockholders to amend or adopt any provision of our bylaws;

•after the Voting Threshold Date our stockholders will only be able to take action at a meeting of stockholders, and will not be able to take action by written consent for any matter;

•until the Voting Threshold Date, our stockholders will be able to act by written consent only if the action is first recommended or approved by the Board of Directors;

•vacancies on our Board of Directors will be able to be filled only by our Board of Directors and not by stockholders;

•only the chairman of our Board of Directors, our chief executive officer, a majority of our Board of Directors, or, until the Class B common stock, as a class, converts to Class A common stock, a stockholder holding thirty percent of the combined voting power of our Class A and Class B common stock are authorized to call a special meeting of stockholders;

•certain litigation against us may be required to be brought in Delaware;

•our restated certificate of incorporation authorizes undesignated preferred stock, the terms of which may be established and shares of which may be issued, without the approval of the holders of Class A common stock; and

•advance notice procedures apply for stockholders to nominate candidates for election as directors or to bring matters before an annual meeting of stockholders.

~~Table of Contents~~

These anti-takeover defenses could discourage, delay, or prevent a transaction involving a change in control of our company. These provisions could also discourage proxy contests and make it more difficult for stockholders to elect directors of their choosing and to cause us to take other corporate actions they desire, any of which, under certain circumstances, could

Table of Contents

limit the opportunity for our stockholders to receive a premium for their shares of our capital stock, and could also affect the price that some investors are willing to pay for our Class A common stock.

Our amended and restated bylaws designate a state or federal court located within the State of Delaware as the exclusive forum for substantially all disputes between us and our stockholders, and also provide that the federal district courts will be the exclusive forum for resolving any complaint asserting a cause of action arising under the Securities Act, each of which could limit our stockholders’ ability to choose the judicial forum for disputes with us or our directors, officers, or employees.

Our amended and restated bylaws provide that, unless we consent in writing to the selection of an alternative forum, the sole and exclusive forum for (1) any derivative action or proceeding brought on our behalf, (2) any action asserting a claim of breach of a fiduciary duty owed by any of our directors, officers, or other employees to us or our stockholders, (3) any action arising pursuant to any provision of the Delaware General Corporation Law, or the certificate of incorporation or the amended and restated bylaws, or (4) any other action asserting a claim that is governed by the internal affairs doctrine shall be the Court of Chancery of the State of Delaware (or, if the Court of Chancery does not have jurisdiction, the federal district court for the District of Delaware), in all cases subject to the court having jurisdiction over indispensable parties named as defendants.

Our amended and restated bylaws also provide that the federal district courts of the United States of America will be the exclusive forum for resolving any complaint asserting a cause of action arising under the Securities Act, or a Federal Forum Provision.

Any person or entity purchasing or otherwise acquiring any interest in any of our securities shall be deemed to have notice of and consented to this provision. These exclusive-forum provisions may limit a stockholder’s ability to bring a claim in a judicial forum of its choosing for disputes with us or our directors, officers, or other employees, which may discourage lawsuits against us and our directors, officers, and other employees.

If we face relevant litigation and are unable to enforce these provisions, we may incur additional costs associated with resolving the dispute in other jurisdictions, which could harm our results of operations.

We cannot guarantee that our stock repurchase program will be fully implemented or that it will enhance long-term stockholder value.

In February 2020, our Board of Directors approved a stock repurchase program for the repurchase of up to $600 million of the outstanding shares of our Class A common stock, ~~and~~ in February 2021 our Board of Directors authorized the repurchase of up to an additional $1 billion of the outstanding shares of our Class A common stock and in February 2022 our Board of Directors further authorized the repurchase of up to an additional $1.2 billion of the outstanding shares of our Class A common stock. The repurchase program does not have an expiration date and we are not obligated to repurchase a specified number or dollar value of shares. Share repurchases will be made from time to time in private transactions or open market purchases, as permitted by securities laws and other legal requirements. Although we have previously announced an intention to increase the pace of our share repurchases, any share repurchases remain subject to the circumstances in place at that time, including prevailing market prices. As a result, there can be no guarantee around the timing of our share repurchases, or that the volume of such repurchases will increase. The stock repurchase program could affect the price of our Class A common stock, increase volatility and diminish our cash reserves. Our repurchase program may be suspended or terminated at any time and, even if fully implemented, may not enhance long-term stockholder value.

We do not intend to pay dividends for the foreseeable future.

We have never declared nor paid cash dividends on our capital stock. We currently intend to retain any future earnings to finance the operation and expansion of our business and fund our stock repurchase program, and we do not expect to declare or pay any dividends in the foreseeable future. As a result, stockholders must rely on sales of their Class A common stock after price appreciation as the only way to realize any future gains on their investment. In addition, our revolving credit facility contains restrictions on our ability to pay dividends.

~~Table of Contents~~

General Risk Factors

Our business could be disrupted by catastrophic events.

Occurrence of any catastrophic event, including earthquake, fire, flood, tsunami, or other weather event, power loss, telecommunications failure, software or hardware malfunctions, cyber-attack, war, or terrorist attack, could result in lengthy interruptions in our service or result in unexpected increases in our costs. Further, outbreaks of pandemic diseases, such as

Table of Contents

COVID-19, or the fear of such events, have resulted in responses, including government-imposed travel restrictions, grounding of flights, and shutdown of workplaces. As a result, we are conducting business with substantial modifications, including modifications to employee travel and employee work locations. These modifications may disrupt important business operations, such as our product development and sales and marketing activities, and the productivity of our employees.

Additionally, our U.S. headquarters and some of the datacenters we utilize are located in the San Francisco Bay Area, a region known for seismic activity, and our insurance coverage may not compensate us for losses that may occur in the event of an earthquake or other significant natural disaster. In addition, acts of terrorism could cause disruptions to the internet or the economy as a whole. Even with our disaster recovery arrangements, our service could be interrupted. If our systems were to fail or be negatively impacted as a result of a natural disaster or other event, our ability to deliver products to our users would be impaired, we could lose critical data and we may be subject to increased costs. If we are unable to develop adequate plans to mitigate the impact of a disaster or to ensure that our business functions continue to operate during and after a disaster, and successfully execute on those plans in the event of a disaster or emergency, our business, results of operations, financial condition, and reputation would be harmed.

We may have exposure to greater than anticipated tax liabilities, which could adversely impact our results of operations.

While to date we have not incurred significant income taxes in operating our business, we are subject to income taxes in the United States and various jurisdictions outside of the United States. Our effective tax rate could fluctuate due to changes in the mix of earnings and losses in countries with differing statutory tax rates. Our tax expense could also be impacted by changes in non-deductible expenses, changes in excess tax benefits of stock-based compensation, changes in the valuation of deferred tax assets and liabilities and our ability to utilize them, the applicability of withholding taxes and effects from acquisitions.

Our tax provision could also be impacted by changes in accounting principles, changes in U.S. federal, state, or international tax laws applicable to corporate multinationals such as the recent legislation enacted in the United States, other fundamental law changes currently being considered by many countries, and changes in taxing jurisdictions’ administrative interpretations, decisions, policies, and positions. Additionally, the Organization for Economic Co-Operation and Development has released guidance covering various topics, including digital economy, transfer pricing, country-by-country reporting, and definitional changes to permanent establishment that could ultimately impact our tax liabilities.

We are subject to review and audit by U.S. federal, state, local, and foreign tax authorities. Such tax authorities may disagree with tax positions we take and if any such tax authority were to successfully challenge any such position, our financial results and operations could be materially and adversely affected. We may also be subject to additional tax liabilities due to changes in ~~non income-based~~non-income-based taxes resulting from changes in federal, state, or international tax laws, changes in taxing jurisdictions’ administrative interpretations, decisions, policies, and positions, results of tax examinations, settlements or judicial decisions, changes in accounting principles, changes to the business operations, including acquisitions, as well as the evaluation of new information that results in a change to a tax position taken in a prior period.

If we fail to maintain an effective system of disclosure controls and internal control over financial reporting, our ability to produce timely and accurate financial statements or comply with applicable regulations could be impaired.

We are subject to the reporting requirements of the Exchange Act, the Sarbanes-Oxley Act of 2002, or the Sarbanes-Oxley Act, and the rules and regulations of the applicable listing standards of the Nasdaq Global Select Market, or Nasdaq. We expect that the requirements of these rules and regulations will continue to increase our legal, accounting, and financial compliance costs, make some activities more difficult, time-consuming and costly, and place significant strain on our personnel, systems, and resources.

The Sarbanes-Oxley Act requires, among other things, that we maintain effective disclosure controls and procedures and internal control over financial reporting. We are also required to provide an annual management report on the effectiveness of our disclosure controls and procedures over financial reporting. We are continuing to develop and refine our disclosure controls and other procedures that are designed to ensure that information required to be disclosed by us in the reports that we will file

~~Table of Contents~~

with the SEC is recorded, processed, summarized, and reported within the time periods specified in SEC rules and forms and that information required to be disclosed in reports under the Exchange Act is accumulated and communicated to our principal executive and financial officers. We are also continuing to improve our internal control over financial reporting. In order to maintain and improve the effectiveness of our disclosure controls and procedures and internal control over financial reporting, we have expended, and anticipate that we will continue to expend, significant resources, including accounting-related costs and significant management oversight. In addition, our independent registered public accounting firm is required to audit the effectiveness of our internal control over financial reporting pursuant to Section 404(b) of the Sarbanes-Oxley Act annually. Testing, or the subsequent testing by our independent registered public accounting firm, may reveal material weaknesses or

Table of Contents

significant deficiencies. If material weaknesses are identified or we are not able to comply with the requirements of Section 404 in a timely manner, our reported financial results could be materially misstated, we could receive an adverse opinion regarding our internal control over financial reporting from our independent registered public accounting firm, we could be subject to investigations or sanctions by regulatory authorities and we could incur substantial expenses.

Our current controls and any new controls that we develop may become inadequate because of changes in conditions in our business. Additionally, to the extent we acquire other businesses, the acquired company may not have a sufficiently robust system of internal controls and we may uncover new deficiencies. Weaknesses in our disclosure controls and internal control over financial reporting may be discovered in the future. Any failure to develop or maintain effective controls or any difficulties encountered in their implementation or improvement that could harm our results of operations or cause us to fail to meet our reporting obligations and may result in a restatement of our financial statements for prior periods. Any failure to implement and maintain effective internal control over financial reporting also could adversely affect the results of periodic management evaluations and annual independent registered public accounting firm attestation reports regarding the effectiveness of our internal control over financial reporting that are required to be included in our periodic reports that will be filed with the SEC. Ineffective disclosure controls and procedures and internal control over financial reporting could also cause investors to lose confidence in our reported financial and other information, which would likely have a negative effect on the trading price of our Class A common stock. In addition, if we are unable to continue to meet these requirements, we may not be able to remain listed on Nasdaq.

Our reported results of operations may be adversely affected by changes in accounting principles generally accepted in the United States.

Generally accepted accounting principles in the United States are subject to interpretation by the Financial Accounting Standards Board, or FASB, the SEC, and various bodies formed to promulgate and interpret appropriate accounting principles. A change in these principles or interpretations could have a significant effect on our reported results of operations, and may even affect the reporting of transactions completed before the announcement or effectiveness of a change. It is difficult to predict the impact of future changes to accounting principles or our accounting policies, any of which could negatively affect our results of operations.

We may need additional capital, and we cannot be certain that additional financing will be available on favorable terms, or at all.

Historically, we have funded our operations and capital expenditures primarily through equity issuances, cash generated from our operations, and debt financing for capital purchases. Although we currently anticipate that our existing cash, cash equivalents and short-term investments, amounts available under our existing credit facilities, and cash flow from operations will be sufficient to meet our cash needs for the foreseeable future, we may require additional financing. We evaluate financing opportunities from time to time, and our ability to obtain financing will depend, among other things, on our development efforts, business plans, operating performance, and condition of the capital markets at the time we seek financing. We cannot assure you that additional financing will be available to us on favorable terms when required, or at all. If we raise additional funds through the issuance of equity or equity-linked or debt securities, those securities may have rights, preferences or privileges senior to the rights of our Class A common stock, and our stockholders may experience dilution.

Our Class A common stock market price and trading volume could decline if securities or industry analysts do not publish research or publish inaccurate or unfavorable research about our business.

The trading market for our Class A common stock will depend in part on the research and reports that securities or industry analysts publish about us or our business. The analysts’ estimates are based upon their own opinions and are often different from our estimates or expectations. If one or more of the analysts who cover us downgrade our Class A common stock or publish inaccurate or unfavorable research about our business, the price of our securities would likely decline. If few securities analysts commence coverage of us, or if one or more of these analysts cease coverage of us or fail to publish reports

~~Table of Contents~~

on us regularly, demand for our securities could decrease, which might cause the price and trading volume of our Class A common stock to decline.

9584

Table of Contents

ITEM 2. UNREGISTERED SALES OF EQUITY SECURITIES AND USE OF PROCEEDS

Issuer Purchases of Equity Securities

The following table presents information with respect to Dropbox's repurchases of Class A common stock during the

quarter ended ~~September 30, 2021.~~March 31, 2022.

Period
Total Number of Shares Purchased (in millions)(1)
Average Price Paid per Share(2)
Total Number of Shares Purchased as Part of Publicly Announced Programs
(in millions)(1)
Approximate Dollar Value of Shares that May Yet Be Purchased Under Publicly Announced Programs
(in millions)(1)
July 1 - 31 1.03 $ 30.67 1.03 $ 787.96
August 1 - 31 2.15 $ 31.31 2.15 $ 720.52
September 1 - 30 2.65 $ 30.91 2.65 $ 638.50
Total 5.83 $ 31.00 5.83


Period	Total Number of Shares Purchased (in millions)(1)	Average Price Paid per Share(2)		Total Number of Shares Purchased as Part of Publicly Announced Programs (in millions)(1)	Approximate Dollar Value of Shares that May Yet Be Purchased Under Publicly Announced Programs (in millions)(1)
January 1 - 31	4.72	$	23.95	4.72	$	230.48
February 1 - 28	3.82(3)	$	24.07	3.59	$	1,344.10
March 1 - 31	2.72	$	22.24	2.72	$	1,283.53
Total	11.26	$	23.57	11.03

(1) On February 20, 2020, we announced that our Board of Directors approved a stock repurchase program for the repurchase of up to $600 million of the Company's outstanding shares of Class A common stock. On February 18, 2021, we announced that our Board of Directors authorized the repurchase of an additional $1 billion of the outstanding shares of our Class A common stock. We completed the February 2020 authorization of ~~$600~~$600 million during the three months ended March 31, 2021 and continued stock repurchases under the February 2021 authorization. On February 17, 2022, we announced that our Board of Directors authorized the repurchase of an additional $1.2 billion of the outstanding shares of our Class A common stock. Under this program, shares may be repurchased, subject to general business and market conditions and other investment opportunities, through open market purchases or privately held negotiated transactions, including through Rule 10b5-1 plans, in each case as permitted by securities laws and other legal requirements. The repurchase program does not have an expiration date. See Note 12 "Stockholders' ~~(Deficit) Equity" of~~Deficit to our condensed consolidated financial statements included elsewhere in this Quarterly Report on Form 10-Q for additional information related to share repurchases.

(2) Average price paid per share includes costs associated with the repurchases.

(3) Includes 228,677 shares of restricted common stock withheld by the Company upon vesting of restricted stock awards to satisfy tax withholding requirements.

ITEM 6. EXHIBITS

We have filed the exhibits listed on the accompanying Exhibit Index, which is incorporated herein by reference.

9685

Table of Contents

EXHIBIT INDEX

Exhibit
Number

Description

Form

File Number

Incorporated by Reference from Exhibit Number

Filed with SEC

31.1

Certification of Principal Executive Officer pursuant to Exchange Act Rules 13a-14(a) and 15d-14(a), as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.

31.2

Certification of Principal Financial Officer pursuant to Exchange Act Rules 13a-14(a) and 15d-14(a), as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.

32.1†

Certifications of Principal Executive Officer and Principal Financial Officer pursuant to 18 U.S.C. Section 1350 as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.

101

The following financial statements from the Company's Quarterly Report on Form 10-Q for the quarter ended ~~September 30, 2021,~~March 31, 2022, formatted in Inline XBRL: (i) Condensed Consolidated Balance Sheets, (ii) Condensed Consolidated Statement of Operations, (iii) Condensed Consolidated Statements of Comprehensive Income, (iv) Condensed Consolidated Statements of Cash Flows, (v) Condensed Consolidated Statements of Stockholders' ~~(Deficit) Equity,~~Deficit, and (vi) Notes to Unaudited Condensed Consolidated Financial Statements.

104

Cover Page Interactive Data File (formatted as inline XBRL and contained in Exhibit 101)

† The certifications attached as Exhibit 32.1 that accompany this Quarterly Report on Form 10-Q are deemed furnished and not filed with the Securities and Exchange Commission and are not to be incorporated by reference into any filing of Dropbox, Inc. under the Securities Act of 1933, as amended, or the Securities Exchange Act of 1934, as amended, whether made before or after the date of this Quarterly Report on Form 10-Q, irrespective of any general incorporation language contained in such filing.

9786

Table of Contents

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

DROPBOX, INC.

Date:

~~November 5, 2021~~May 6, 2022

By:

/s/Andrew W. Houston

Andrew W. Houston

Chief Executive Officer

(Principal Executive Officer)

Date:

~~November 5, 2021~~May 6, 2022

By:

/s/ Timothy J. Regan

Timothy J. Regan

Chief Financial Officer

(Principal Accounting and Financial Officer)

9887


Delaware						26-0138832
(State or other jurisdiction of incorporation or organization)						(I.R.S. Employer Identification Number)


		Page
	PART I. FINANCIAL INFORMATION
Item 1.	Condensed Consolidated Financial Statements (Unaudited)	76
	Condensed Consolidated Balance Sheets as of Se ~~ptember~~ ~~30, 2021~~March 31, 2022 and December 31, ~~2020~~2021	76
	Condensed Consolidated Statements of Operations for the Three ~~and~~ ~~Nine~~Months Ended ~~September~~March 31 , 202 2 ~~30, 2021~~ and ~~2020~~202 1	87
	Condensed Consolidated Statements of Comprehensive Income for the Three ~~and~~ ~~Nine~~Months Ended ~~September~~March 31 , 202 2 ~~30, 2021~~ and ~~2020~~202 1	98
	Condensed Consolidated Statements of Stockholders' ~~(Deficit) Equity~~Deficit for the Three ~~and~~ ~~Nine~~ Months Ended ~~September~~March 31 , 202 2 ~~30, 2021~~ and ~~2020~~202 1	109
	Condensed Consolidated Statements of Cash Flows for the ~~Nine~~Three Months Ended ~~September~~March 3 1 , 202 2 ~~30, 2021~~ and ~~2020~~202 1	1210
	Notes to Condensed Consolidated Financial Statements	1311
Item 2.	Management's Discussion and Analysis of Financial Condition and Results of Operations	4338
Item 3.	Quantitative and Qualitative Disclosures About Market Risk	6654
Item 4.	Controls and Procedures	6755

	PART II. OTHER INFORMATION
Item 1.	Legal Proceedings	6856
Item 1A.	Risk Factors	6957
Item 2.	Unregistered Sales of Equity Securities and Use of Proceeds	9785
Item 6.	Exhibits	9785
	Exhibit Index	9886
	Signatures	9987


		As of					As of
		September 30, 2021		December 31, 2020			March 31, 2022		December 31, 2021

Assets	Assets					Assets
Current assets:	Current assets:					Current assets:
Cash and cash equivalents	Cash and cash equivalents	$	688.9	$	314.9	Cash and cash equivalents	$	445.5	$	533.0
Short-term investments	Short-term investments	1,239.8		806.4		Short-term investments	1,050.1		1,185.1
Trade and other receivables, net	Trade and other receivables, net	40.9		43.4		Trade and other receivables, net	44.6		49.6
Prepaid expenses and other current assets	Prepaid expenses and other current assets	86.7		62.8		Prepaid expenses and other current assets	82.7		82.1
Total current assets	Total current assets	2,056.3		1,227.5		Total current assets	1,622.9		1,849.8
Property and equipment, net	Property and equipment, net	345.8		338.7		Property and equipment, net	316.1		322.0
Operating lease right-of-use asset	Operating lease right-of-use asset	464.8		470.5		Operating lease right-of-use asset	420.3		413.9
Intangible assets, net	Intangible assets, net	49.6		33.5		Intangible assets, net	50.0		53.6
Goodwill	Goodwill	347.2		236.9		Goodwill	355.9		356.6
Other assets	Other assets	75.4		80.1		Other assets	86.8		95.4
Total assets	Total assets	$	3,339.1	$	2,387.2	Total assets	$	2,852.0	$	3,091.3
Liabilities and stockholders' (deficit) equity
Liabilities and stockholders' deficit						Liabilities and stockholders' deficit
Current liabilities:	Current liabilities:					Current liabilities:
Accounts payable	Accounts payable	$	23.0	$	18.7	Accounts payable	$	24.4	$	25.7
Accrued and other current liabilities	Accrued and other current liabilities	170.9		156.7		Accrued and other current liabilities	155.2		140.8
Accrued compensation and benefits	Accrued compensation and benefits	107.1		113.6		Accrued compensation and benefits	44.6		139.1
Operating lease liability	Operating lease liability	85.2		88.7		Operating lease liability	82.6		78.3
Finance lease obligation	Finance lease obligation	120.9		99.6		Finance lease obligation	118.9		120.4
Deferred revenue	Deferred revenue	668.0		610.5		Deferred revenue	691.7		671.5
Total current liabilities	Total current liabilities	1,175.1		1,087.8		Total current liabilities	1,117.4		1,175.8
Operating lease liability, non-current	Operating lease liability, non-current	743.6		759.6		Operating lease liability, non-current	632.3		632.0
Finance lease obligation, non-current	Finance lease obligation, non-current	182.2		171.6		Finance lease obligation, non-current	156.6		167.7
Convertible senior notes, net, non-current	Convertible senior notes, net, non-current	1,369.3		—		Convertible senior notes, net, non-current	1,371.2		1,370.3
Other non-current liabilities	Other non-current liabilities	31.5		34.4		Other non-current liabilities	37.8		39.4
Total liabilities	Total liabilities	3,501.7		2,053.4		Total liabilities	3,315.3		3,385.2
Commitments and contingencies (Note 10)	Commitments and contingencies (Note 10)	0		0		Commitments and contingencies (Note 10)	0		0
Stockholders' (deficit) equity:
Stockholders' deficit:						Stockholders' deficit:
Additional paid-in-capital	Additional paid-in-capital	2,468.1		2,564.3		Additional paid-in-capital	2,419.7		2,448.1
Accumulated deficit	Accumulated deficit	(2,635.5)		(2,241.4)		Accumulated deficit	(2,854.9)		(2,739.4)
Accumulated other comprehensive income		4.8		10.9
Total stockholders' (deficit) equity		(162.6)		333.8
Total liabilities and stockholders' (deficit) equity		$	3,339.1	$	2,387.2
Accumulated other comprehensive loss						Accumulated other comprehensive loss	(28.1)		(2.6)
Total stockholders' deficit						Total stockholders' deficit	(463.3)		(293.9)
Total liabilities and stockholders' deficit						Total liabilities and stockholders' deficit	$	2,852.0	$	3,091.3


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
		2021		2020		2021		2020			2022		2021

Revenue	Revenue	$	550.2	$	487.4	$	1,592.4	$	1,409.8	Revenue	$	562.4	$	511.6
Cost of revenue(1)	Cost of revenue(1)	112.0		103.2		328.4		308.8		Cost of revenue(1)	112.9		109.3
Gross profit	Gross profit	438.2		384.2		1,264.0		1,101.0		Gross profit	449.5		402.3
Operating expenses(1)	Operating expenses(1)									Operating expenses(1)
Research and development	Research and development	187.3		183.3		554.0		550.9		Research and development	210.8		181.2
Sales and marketing	Sales and marketing	115.7		105.8		319.2		312.9		Sales and marketing	95.7		102.7
General and administrative	General and administrative	57.9		65.1		169.3		167.6		General and administrative	53.5		58.6
Impairment related to real estate assets(2)	Impairment related to real estate assets(2)	—		—		17.3		—		Impairment related to real estate assets(2)	—		17.3
Total operating expenses	Total operating expenses	360.9		354.2		1,059.8		1,031.4		Total operating expenses	360.0		359.8
Income from operations	Income from operations	77.3		30.0		204.2		69.6		Income from operations	89.5		42.5
Interest income (expense), net		(1.7)		0.1		(3.8)		2.6
Interest expense, net										Interest expense, net	(1.4)		(1.2)
Other income, net	Other income, net	0.5		3.5		13.1		23.1		Other income, net	5.7		5.1
Income before income taxes	Income before income taxes	76.1		33.6		213.5		95.3		Income before income taxes	93.8		46.4
Provision for income taxes		(0.5)		(0.9)		(2.3)		(5.8)
(Provision for) benefit from income taxes										(Provision for) benefit from income taxes	(14.1)		1.2
Net income	Net income	$	75.6	$	32.7	$	211.2	$	89.5	Net income	$	79.7	$	47.6
Net income per share-basic and diluted:	Net income per share-basic and diluted:									Net income per share-basic and diluted:
Basic net income per share	Basic net income per share	$	0.20	$	0.08	$	0.54	$	0.22	Basic net income per share	$	0.22	$	0.12
Diluted net income per share	Diluted net income per share	$	0.19	$	0.08	$	0.53	$	0.21	Diluted net income per share	$	0.21	$	0.12
Weighted-average shares used in computing net income per share attributable to common stockholders, basic	Weighted-average shares used in computing net income per share attributable to common stockholders, basic	385.5		414.2		390.6		415.2		Weighted-average shares used in computing net income per share attributable to common stockholders, basic	370.7		398.1
Weighted-average shares used in computing net income per share attributable to common stockholders, diluted	Weighted-average shares used in computing net income per share attributable to common stockholders, diluted	398.1		419.9		400.3		419.9		Weighted-average shares used in computing net income per share attributable to common stockholders, diluted	372.9		405.4


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
		2021		2020		2021		2020			2022		2021

Cost of revenue	Cost of revenue	$	6.0	$	4.6	$	17.3	$	12.6	Cost of revenue	$	5.7	$	5.4
Research and development	Research and development	48.7		46.9		141.7		131.1		Research and development	50.5		43.5
Sales and marketing	Sales and marketing	5.9		8.9		19.0		25.1		Sales and marketing	4.5		6.9
General and administrative~~(2)~~	General and administrative~~(2)~~	12.2		15.3		36.6		23.3		General and administrative~~(2)~~	11.6		12.1


	Three Months Ended September 30, 2021											Three Months Ended September 30, 2020
	Class A and Class B Common Stock			Additional paid in capital		Accumulated deficit		Accumulated other comprehensive income		Total stockholders' (deficit) equity		Class A and Class B common stock			Additional paid-in capital		Accumulated deficit		Accumulated other comprehensive income (loss)		Total stockholders’ equity
	Shares	Amount										Shares	Amount
Balances at beginning of period	386.5	$	—	$	2,446.9	$	(2,547.5)	$	5.8	$	(94.8)	413.8	$	—	$	2,560.4	$	(1,764.4)	$	7.4	$	803.4
Release of restricted stock units and awards	3.1	—		—		—		—		—		3.3	—		—		—		—		—
Shares withheld related to net share settlement of restricted stock units and awards	(1.1)	—		(8.3)		(27.2)		—		(35.5)		(1.1)	—		(10.6)		(11.9)		—		(22.5)
Repurchases of common stock	(5.8)	—		(44.6)		(136.4)		—		(181.0)		(1.8)	—		(16.8)		(20.7)		—		(37.5)
Exercise of stock options and awards	0.1	—		1.1		—		—		1.1		0.1	—		0.1		—		—		0.1



Tax benefit attributable to bond hedges purchased in connection with issuance of convertible senior notes	—	—		0.2		—		—		0.2		—	—		—		—		—		—
Stock-based compensation	—	—		72.8		—		—		72.8		—	—		75.7		—		—		75.7
Other comprehensive loss	—	—		—		—		(1.0)		(1.0)		—	—		—		—		(0.6)		(0.6)
Net income	—	—		—		75.6		—		75.6		—	—		—		32.7		—		32.7
Balances at end of period	382.8	$	—	$	2,468.1	$	(2,635.5)	$	4.8	$	(162.6)	414.3	$	—	$	2,608.8	$	(1,764.3)	$	6.8	$	851.3


		Nine Months Ended September 30, 2021														Nine Months Ended September 30, 2020																							Three Months Ended March 31, 2022																														Three Months Ended March 31, 2021
		Class A and Class B Common Stock			Additional paid in capital				Accumulated deficit		Accumulated other comprehensive income			Total stockholders' (deficit) equity		Class A and Class B common stock					Additional paid-in capital				Accumulated deficit				Accumulated other comprehensive income					Total stockholders’ equity					Class A and Class B Common Stock								Additional paid in capital						Accumulated deficit					Accumulated other comprehensive income						Total stockholders' deficit					Class A and Class B common stock									Additional paid-in capital					Accumulated deficit					Accumulated other comprehensive income					Total stockholders' deficit
		Shares	Amount										Shares			Amount				Shares																	Amount														Shares										Amount
Balances at beginning of period	Balances at beginning of period	405.7	$	—			$	2,564.3			$	(2,241.4)		$	10.9	$	333.8	417.0					$	—			$	2,531.3			$	(1,726.2)				$	3.3			$	808.4		Balances at beginning of period		375.5					$	—					$	2,448.1					$	(2,739.4)				$	(2.6)			$	(293.9)				405.7					$	—				$	2,564.3				$	(2,241.4)				$	10.9	$	333.8
Release of restricted stock units and awards	Release of restricted stock units and awards	10.0	—		—				—		—			—		9.4		—			—				—				—					—			Release of restricted stock units and awards		3.9				—						—						—					—						—				3.8					—					—					—					—					—
Shares withheld related to net share settlement of restricted stock units and awards	Shares withheld related to net share settlement of restricted stock units and awards	(3.6)	—		(27.6)				(70.6)		—			(98.2)		(3.3)		—			(31.0)				(35.5)				—					(66.5)			Shares withheld related to net share settlement of restricted stock units and awards		(1.5)				—				(12.2)						(24.5)					—						(36.7)					(1.5)				—					(11.2)					(24.6)					—					(35.8)
Repurchases of common stock	Repurchases of common stock	(29.9)	—		(229.0)				(534.7)		—			(763.7)		(9.2)		—			(85.2)				(92.1)				—					(177.3)			Repurchases of common stock		(11.0)				—				(89.2)						(170.7)					—						(259.9)					(18.6)				—					(142.5)					(289.4)					—					(431.9)
Exercise of stock options and awards	Exercise of stock options and awards	0.6	—		6.6				—		—			6.6		0.4		—			1.6				—				—					1.6			Exercise of stock options and awards		0.1				—				0.2						—					—						0.2					0.4				—					2.9					—					—					2.9
Assumed stock options in connection with acquisition	Assumed stock options in connection with acquisition	—	—		1.2				—		—			1.2		—		—			—				—				—					—			Assumed stock options in connection with acquisition		—				—				—						—					—						—					—				—					1.2					—					—					1.2
Purchase of bond hedges in connection with issuance of convertible senior notes	Purchase of bond hedges in connection with issuance of convertible senior notes	—	—		(265.3)				—		—			(265.3)		—		—			—				—				—					—			Purchase of bond hedges in connection with issuance of convertible senior notes		—				—				—						—					—						—					—				—					(265.3)					—					—					(265.3)
Sale of warrants in connection with issuance of convertible senior notes	Sale of warrants in connection with issuance of convertible senior notes	—	—		202.9				—		—			202.9		—		—			—				—				—					—			Sale of warrants in connection with issuance of convertible senior notes		—				—				—						—					—						—					—				—					202.9					—					—					202.9
Tax benefit attributable to bond hedges purchased in connection with issuance of convertible senior notes	Tax benefit attributable to bond hedges purchased in connection with issuance of convertible senior notes	—	—		0.4				—		—			0.4		—		—			—				—				—					—			Tax benefit attributable to bond hedges purchased in connection with issuance of convertible senior notes		—				—				0.5						—					—						0.5					—				—					—					—					—					—
Stock-based compensation	Stock-based compensation	—	—		214.6				—		—			214.6		—		—			192.1				—				—					192.1			Stock-based compensation		—				—				72.3						—					—						72.3					—				—					67.9					—					—					67.9
Other comprehensive income (loss)		—	—		—				—		(6.1)			(6.1)		—		—			—				—				3.5					3.5
Other comprehensive loss																															Other comprehensive loss		—					—				—				—						(25.5)					(25.5)						—					—				—					—					(6.3)					(6.3)
Net income	Net income	—	—		—				211.2		—			211.2		—		—			—				89.5				—					89.5			Net income		—				—				—						79.7					—						79.7					—				—					—					47.6					—					47.6
Balances at end of period	Balances at end of period	382.8	$	—	$	2,468.1			$	(2,635.5)	$	4.8		$	(162.6)	414.3		$	—		$	2,608.8			$	(1,764.3)			$	6.8				$	851.3		Balances at end of period		367.0				$	—			$	2,419.7					$	(2,854.9)				$	(28.1)					$	(463.3)				389.8				$	—				$	2,420.2				$	(2,507.8)				$	4.6				$	(83.0)


Property and equipment						Useful life

Buildings						20 to 30 years
Datacenter and other computer equipment						3 to 5 years
Office equipment and other						3 to 7 years
Leasehold improvements						Lesser of estimated useful life or remaining lease term


		As of September 30, 2021
		Amortized Cost		Unrealized Gain		Unrealized Loss		Estimated Fair Value			As of March 31, 2022
											Amortized Cost		Unrealized Gain		Unrealized Loss		Estimated Fair Value
Cash	Cash	$	85.8	$	—	$	—	$	85.8	Cash	$	85.8	$	—	$	—	$	85.8
Cash equivalents	Cash equivalents									Cash equivalents
Money market funds	Money market funds	595.3		—		—		$	595.3	Money market funds	349.7		—		—		$	349.7
Commercial paper	Commercial paper	4.5		—		—		$	4.5	Commercial paper	10.0		—		—		$	10.0
Certificates of deposit		2.0		—		—		$	2.0
Corporate notes and obligations		1.3		—		—		1.3
Total cash & cash equivalents	Total cash & cash equivalents	$	688.9	$	—	$	—	$	688.9	Total cash & cash equivalents	$	445.5	$	—	$	—	$	445.5
Short-term investments	Short-term investments									Short-term investments
Corporate notes and obligations	Corporate notes and obligations	597.1		1.1		(1.1)		597.1		Corporate notes and obligations	531.7		—		(15.6)		516.1
U.S. Treasury securities	U.S. Treasury securities	234.2		0.1		(1.2)		233.1		U.S. Treasury securities	264.6		—		(9.2)		255.4
Asset backed securities	Asset backed securities	144.0		0.2		(0.2)		144.0		Asset backed securities	138.7		—		(4.4)		134.3
Municipal securities										Municipal securities	68.7		—		(2.8)		65.9
Commercial paper	Commercial paper	95.6		—		—		95.6		Commercial paper	24.4		—		—		24.4
Municipal securities		71.0		0.1		(0.2)		70.9
Certificates of deposit	Certificates of deposit	56.3		—		—		56.3		Certificates of deposit	19.0		—		—		19.0
U.S. agency obligations										U.S. agency obligations	14.5		—		(0.5)		14.0
Foreign government obligations	Foreign government obligations	18.4		—		—		18.4		Foreign government obligations	13.5		—		(0.3)		13.2
U.S. agency obligations		14.5		—		(0.1)		14.4
Supranational Securities		10.0		—		—		10.0
Supranational securities										Supranational securities	8.0		—		(0.2)		7.8
Total short-term investments	Total short-term investments	1,241.1		1.5		(2.8)		1,239.8		Total short-term investments	1,083.1		—		(33.0)		1,050.1
Total	Total	$	1,930.0	1.5		$	(2.8)	$	1,928.7	Total	$	1,528.6	—		$	(33.0)	$	1,495.6


	As of December 31, 2021
	Amortized Cost		Unrealized Gain		Unrealized Loss		Estimated Fair Value
Cash	$	142.7	$	—	$	—	$	142.7
Cash equivalents
Money market funds	390.3		—		—		390.3
Total cash & cash equivalents	$	533.0	$	—	$	—	$	533.0
Short-term investments
Corporate notes and obligations	607.4		0.4		(4.0)		603.8
U.S. Treasury securities	240.4		—		(2.9)		237.5
Asset backed securities	140.7		0.1		(1.2)		139.6
Municipal securities	70.5		—		(0.7)		69.8
Commercial paper	61.7		—		—		61.7
Certificates of deposit	32.1		—		—		32.1
Foreign government obligations	18.4		—		(0.1)		18.3
U.S. agency obligations	14.6		—		(0.2)		14.4
Supranational securities	8.0		—		(0.1)		7.9
Total short-term investments	1,193.8		0.5		(9.2)		1,185.1
Total	$	1,726.8	0.5		$	(9.2)	$	1,718.1


	As of March 31, 2022
	Less than 12 months				More than 12 months				Total
	Fair Value		Gross Unrealized Losses		Fair Value		Gross Unrealized Losses		Fair Value		Gross Unrealized Losses
Corporate notes and obligations	$	444.2	$	(13.5)	$	28.9	$	(2.1)	$	473.1	$	(15.6)
U.S. Treasury securities	173.7		(5.3)		62.1		(3.9)		235.8		(9.2)
Asset backed securities	117.9		(4.1)		9.5		(0.3)		127.4		(4.4)
Municipal securities	56.3		(2.3)		9.5		(0.5)		65.8		(2.8)
U.S. agency obligations	10.5		(0.3)		3.5		(0.2)		14.0		(0.5)
Foreign government obligations	11.3		(0.2)		1.9		(0.1)		13.2		(0.3)
Supranational securities	6.1		(0.1)		1.6		(0.1)		7.7		(0.2)
Total	$	820.0	$	(25.8)	$	117.0	$	(7.2)	$	937.0	$	(33.0)


		As of December 31, 2020									As of December 31, 2021
		Amortized Cost		Unrealized Gain		Unrealized Loss		Estimated Fair Value			Less than 12 months				More than 12 months				Total
											Fair Value		Gross Unrealized Losses		Fair Value		Gross Unrealized Losses		Fair Value		Gross Unrealized Losses
Cash		$	67.2	$	—	$	—	$	67.2
Cash equivalents
Money market funds		222.6		—		—		222.6

U.S. Treasury securities		10.6		—		—		10.6
Commercial paper		8.0		—		—		8.0
Corporate notes and obligations		5.0		—		—		5.0
Municipal securities		1.5						1.5
Total cash and cash equivalents		$	314.9	$	—	$	—	314.9
Short-term investments
Corporate notes and obligations	Corporate notes and obligations	374.3		2.5		(0.1)		376.7		Corporate notes and obligations	$	498.6	$	(4.1)	$	—	$	—	$	498.6	$	(4.1)
U.S. Treasury securities	U.S. Treasury securities	215.4		1.0		—		216.4		U.S. Treasury securities	218.0		(2.9)		—		—		218.0		(2.9)
Asset backed securities	Asset backed securities	73.5		0.6		—		74.1		Asset backed securities	120.7		(1.2)		—		—		120.7		(1.2)
Municipal securities	Municipal securities	38.7		0.1		—		38.8		Municipal securities	66.0		(0.7)		—		—		66.0		(0.7)
U.S. agency obligations	U.S. agency obligations	23.0		0.1		—		23.1		U.S. agency obligations	14.4		(0.2)		—		—		14.4		(0.2)
Commercial paper		22.5		—		—		22.5
Supranational Securities		18.7		—		—		18.7
Foreign government obligations	Foreign government obligations	18.5		—		—		18.5		Foreign government obligations	15.4		—		—		—		15.4		—
Certificates of deposit		17.6		—		—		17.6
Total short-term investments		802.2		4.3		(0.1)		806.4
Supranational securities										Supranational securities	7.9		(0.1)		—		—		7.9		(0.1)
Total	Total	$	1,117.1	$	4.3	$	(0.1)	$	1,121.3	Total	$	941.0	$	(9.2)	$	—	$	—	$	941.0	$	(9.2)


		As of September 30, 2021
		Level 1		Level 2		Level 3		Total			As of March 31, 2022
											Level 1		Level 2		Level 3		Total
Cash equivalents	Cash equivalents									Cash equivalents
Money market funds	Money market funds	$	595.3	$	—	$	—	$	595.3	Money market funds	$	349.7	$	—	$	—	$	349.7
Commercial paper	Commercial paper	—		4.5		—		4.5		Commercial paper	—		10.0		—		10.0
Certificates of deposit		—		2.0		—		2.0
Corporate notes and obligations		—		1.3		—		1.3
Total cash equivalents	Total cash equivalents	$	595.3	$	7.8	$	—	$	603.1	Total cash equivalents	$	349.7	$	10.0	$	—	$	359.7
Short-term investments	Short-term investments									Short-term investments
Corporate notes and obligations	Corporate notes and obligations	—		597.1		—		597.1		Corporate notes and obligations	—		516.1		—		516.1
U.S. Treasury securities	U.S. Treasury securities	—		233.1		—		233.1		U.S. Treasury securities	—		255.4		—		255.4
Asset backed securities	Asset backed securities	—		144.0		—		144.0		Asset backed securities	—		134.3		—		134.3
Commercial paper	Commercial paper	—		95.6		—		95.6		Commercial paper	—		24.4		—		24.4
Municipal securities	Municipal securities	—		70.9		—		70.9		Municipal securities	—		65.9		—		65.9
Certificates of deposit	Certificates of deposit	—		56.3		—		56.3		Certificates of deposit	—		19.0		—		19.0
U.S. agency obligations										U.S. agency obligations	—		14.0		—		14.0
Foreign government obligations	Foreign government obligations	—		18.4		—		18.4		Foreign government obligations	—		13.2		—		13.2
U.S. agency obligations		—		14.4		—		14.4
Supranational Securities		—		10.0		—		10.0
Supranational securities										Supranational securities	—		7.8		—		7.8
Total short-term investments	Total short-term investments	—		1,239.8		—		1,239.8		Total short-term investments	—		1,050.1		—		1,050.1
Total	Total	$	595.3	$	1,247.6	$	—	$	1,842.9	Total	$	349.7	$	1,060.1	$	—	$	1,409.8


	Purchase consideration
Cash paid to common and preferred stockholders and vested option holders	$	125.5
Transaction costs paid by Dropbox on behalf of DocSend	5.0
Fair value of assumed DocSend options attributable to pre-combination services(1)	1.2
Purchase price adjustments	~~(0.1)~~0.1
Total purchase consideration	$	~~131.6~~131.8


Assets acquired:
Cash and cash equivalents	$	5.1
Acquisition-related intangible assets	20.6
Accounts receivable, prepaid and other assets	6.1
Total assets acquired	$	31.8

Liabilities assumed:
Accounts payable, accrued and other liabilities	$	6.4
Deferred revenue	1.9
Deferred tax liability	1.9
Total liabilities assumed	10.2
Net assets acquired, excluding goodwill	21.6
Total purchase consideration	~~131.6~~131.8
Goodwill(2)	$	~~110.0~~110.2


~~Assets acquired:~~
~~Cash and cash equivalents~~	$	~~5.5~~
~~Short-term investments~~	~~7.8~~
~~Acquisition-related intangible assets~~	~~44.6~~
~~Accounts receivable, prepaid and other assets~~	~~5.0~~
~~Total assets acquired~~	$	~~62.9~~

~~Liabilities assumed:~~
~~Accounts payable, accrued and other liabilities~~	$	~~6.3~~
~~Deferred revenue~~	~~4.8~~
~~Deferred tax liability~~	~~6.9~~
~~Total liabilities assumed~~	~~18.0~~
~~Net assets acquired, excluding goodwill~~	~~44.9~~
~~Total purchase consideration~~	~~177.9~~
~~Goodwill(2)~~	$	~~133.0~~


	2026 Notes		2028 Notes		Total
Principal balance	$	695.8	$	693.3	$	1,389.1
Unamortized issuance costs	(9.7)		(10.1)		(19.8)
Carrying value, net	686.1		683.2		1,369.3


	2026 Notes		2028 Notes		Total
March 31, 2022
Principal balance	$	695.8	$	693.3	$	1,389.1
Unamortized issuance costs	(8.6)		(9.3)		(17.9)
Carrying value, net	687.2		684.0		1,371.2

December 31, 2021
Principal balance	$	695.8	$	693.3	$	1,389.1
Unamortized issuance costs	(9.1)		(9.7)		(18.8)
Carrying value, net	686.7		683.6		1,370.3


	Estimated fair values		Estimated weighted average useful lives (In years)
Developed technology	$	11.5	5.0
Customer relationships	8.1		5.0
Trade name	1.0		5.0
Total acquisition-related intangible assets	$	20.6


	~~Purchase consideration~~
~~Cash paid to common and preferred stockholders and vested option holders~~	$	~~175.2~~
~~Transaction costs paid by Dropbox on behalf of HelloSign~~	~~2.4~~
~~Fair value of assumed HelloSign options attributable to pre-combination services(1)~~	~~0.8~~
~~Purchase price adjustments~~	~~(0.5)~~
~~Total purchase consideration~~	$	~~177.9~~


		As of September 30,		As of December 31,		Weighted- average remaining useful life (In years) As of September 30,		As of March 31,		As of December 31,		Weighted- average remaining useful life (In years) As of March 31,
		2021		2020		2021		2022		2021		2022
Developed technology	Developed technology	$	37.5	$	26.0	3.4	Developed technology	$	45.9	$	45.9	3.5
Customer relationships	Customer relationships	28.6		20.5		3.7	Customer relationships	28.6		28.6		3.4
Patents	Patents	19.5		12.8		5.5	Patents	19.5		19.5		5.1
Software	Software	9.0		9.0		0.9	Software	9.0		9.0		1.1
Trademarks and trade names	Trademarks and trade names	5.6		4.6		2.9	Trademarks and trade names	5.6		5.6		2.5
Licenses	Licenses	4.6		4.6		—	Licenses	4.6		4.6		—
Assembled workforce in asset acquisitions	Assembled workforce in asset acquisitions	3.0		3.0		—	Assembled workforce in asset acquisitions	3.0		3.0		—
Other	Other	0.8		0.8		4.0	Other	1.2		0.8		3.5
Total intangibles	Total intangibles	108.6		81.3			Total intangibles	117.4		117.0
Accumulated amortization	Accumulated amortization	(59.0)		(47.8)			Accumulated amortization	(67.4)		(63.4)
Intangible assets, net	Intangible assets, net	$	49.6	$	33.5		Intangible assets, net	$	50.0	$	53.6


Remaining three months of Fiscal 2021		$	4.2
2022	2022	13.7		2022	11.4
2023	2023	13.2		2023	14.9
2024	2024	8.8		2024	10.5
2025	2025	6.9		2025	8.0
2026				2026	3.7
Thereafter	Thereafter	2.8		Thereafter	1.5
Total	Total	$	49.6	Total	$	50.0


Balance at December 31, ~~2020~~2021	$	~~236.9~~
~~DocSend acquisition~~	~~110.0~~356.6
Effect of foreign currency translation	~~0.3~~ (0.7)
Balance at ~~September 30, 2021~~March 31, 2022	$	~~347.2~~355.9


		Convertible Debt			Convertible Debt
October 1, 2021 through December 31, 2021		$	—
2022		—
April 1, 2022 through December 31, 2022				April 1, 2022 through December 31, 2022	$	—
2023	2023	—		2023	—
2024	2024	—		2024	—
2025	2025	—		2025	—
2026	2026	695.8		2026	695.8
2027				2027	—
Thereafter	Thereafter	693.3		Thereafter	693.3
Total	Total	$	1,389.1	Total	$	1,389.1


Year ending December 31,	Year ending December 31,	Operating leases(1)		Finance leases		Year ending December 31,	Operating leases(1)		Finance leases
2021 (excluding the nine months ended September 30, 2021)		$	30.7	$	34.2
2022		123.2		122.4
2022 (excluding the three months ended March 31, 2022)						2022 (excluding the three months ended March 31, 2022)	$	84.3	$	96.4
2023	2023	106.3		88.8		2023	96.6		98.5
2024	2024	95.7		53.6		2024	86.4		63.4
2025	2025	90.6		15.8		2025	81.0		25.4
2026						2026	61.4		1.2
Thereafter	Thereafter	606.1		—		Thereafter	460.2		—
Total future minimum lease payments	Total future minimum lease payments	1,052.6		314.8		Total future minimum lease payments	869.9		284.9
Less imputed interest	Less imputed interest	(216.4)		(11.7)		Less imputed interest	(151.0)		(9.4)
Less tenant improvement receivables	Less tenant improvement receivables	(7.4)		—		Less tenant improvement receivables	(4.0)		—
Total liability	Total liability	$	828.8	$	303.1	Total liability	$	714.9	$	275.5


Year ending December 31,	Year ending December 31,	Operating leases		Year ending December 31,	Operating leases
2021 (excluding the nine months ended September 30, 2021)		$	4.7
2022		24.3
2022 (excluding the three months ended March 31, 2022)				2022 (excluding the three months ended March 31, 2022)	$	17.8
2023	2023	17.1		2023	14.6
2024	2024	16.5		2024	13.6
2025	2025	15.6		2025	12.6
2026				2026	8.9
Thereafter	Thereafter	82.8		Thereafter	13.3
Total future sublease rent payments	Total future sublease rent payments	161.0		Total future sublease rent payments	80.8
Less sub-tenant incentive	Less sub-tenant incentive	(10.5)		Less sub-tenant incentive	(1.1)
Total future sublease rent payments, net	Total future sublease rent payments, net	$	150.5	Total future sublease rent payments, net	$	79.7


			Options outstanding						Restricted stock outstanding					Options outstanding						Restricted stock outstanding
		Number of shares available for issuance under the Plans	Number of shares outstanding under the Plans	Weighted- average exercise price per share		Weighted- average remaining contractual term (In years)	Aggregate intrinsic value		Number of Plan shares outstanding	Weighted- average grant date fair value per share			Number of shares available for issuance under the Plans	Number of shares outstanding under the Plans	Weighted- average exercise price per share		Weighted- average remaining contractual term (In years)	Aggregate intrinsic value		Number of Plan shares outstanding	Weighted- average grant date fair value per share
Balance at December 31, 2021												Balance at December 31, 2021	95.2	0.9	$	12.09	5.4	$	10.0	27.8	$	24.17
Additional shares authorized												Additional shares authorized	18.8	—	—		—	—		—	—

Balance at December 31, 2020		78.5	1.3	$	13.73	5.7	$	11.35	31.9	$	19.79
Additional shares authorized		20.3	—	—		—	—		—	—
Stock options assumed (1)		0.4	0.4	$	2.17	—	—		—	—
Options exercised and restricted stock units and awards released	Options exercised and restricted stock units and awards released	—	(0.6)	10.15		—	—		(10.0)	20.61		Options exercised and restricted stock units and awards released	—	(0.1)	2.05		—	—		(3.9)	24.65
Options and restricted stock units and awards canceled	Options and restricted stock units and awards canceled	9.3	(0.1)	11.37		—	—		(9.2)	20.77		Options and restricted stock units and awards canceled	2.0	—	4.86		—	—		(1.9)	22.29
Shares withheld related to net share settlement of restricted stock units and awards	Shares withheld related to net share settlement of restricted stock units and awards	3.6	—	—		—	—		—	20.55		Shares withheld related to net share settlement of restricted stock units and awards	1.5	—	—		—	—		—	24.85
Options and restricted stock units and awards granted	Options and restricted stock units and awards granted	(14.7)	—	—		—	—		14.7	26.44		Options and restricted stock units and awards granted	(4.7)	—	—		—	—		4.7	24.04
Balance as of September 30, 2021(2)		97.4	1.0	$	11.70	5.7	$	15.08	27.4	$	22.73
Vested at September 30, 2021			0.5	$	18.47	4.2	$	5.14	—	$	—
Unvested at September 30, 2021			0.5	$	3.39		$	9.94	27.4	$	22.73
Balance as of March 31, 2022												Balance as of March 31, 2022	112.8	0.8	$	13.38	5.0	$	7.1	26.7	$	24.22
Vested at March 31, 2022												Vested at March 31, 2022		0.5	$	17.53	4.0	$	3.2	—	$	—
Unvested at March 31, 2022												Unvested at March 31, 2022		0.3	$	3.20		$	3.9	26.7	$	24.22


Expected volatility	47	%
Expected term (in years)	2.0 - 6.8
Risk-free interest rate	0.15% - 1.29%
Dividend yield	—	%