UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

(Amendment No.     )

Filed by the Registrant  ☒                             Filed by a Party other than the Registrant  ☐

Check the appropriate box:

Heritage Insurance Holdings, Inc.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

Heritage Insurance Holdings, Inc.

2600 McCormick Drive Suite 300

Clearwater, Florida 33759

April 28, 202015, 2021

To Our Stockholders:

On behalf of the Board of Directors and management of Heritage Insurance Holdings, Inc., we cordially invite you to virtually attend the annual meeting of stockholders to be held on June 22, 2020,May 25, 2021 at 10:00 a.m. (ET), at. Due to the Grand Hyatt Tampa Bay, 2900 Bayport Dr., Tampa, Florida 33607.public health impact of the coronavirus (COVID-19) pandemic, and to support the health and well-being of our employees and stockholders, the meeting will be held in a completely virtual meeting only format via live audio webcast.

The following pages contain the formal notice of the annual meeting, the proxy statement and the proxy card. Please review this material for information concerning the business to be conducted at the meeting and the nominees for election as directors. You may also find electronic copies of these documents online at http://www.edocumentview.com/HRTG.

The purpose of the meeting is to consider and vote upon proposals to (i) elect tennine directors, (ii) ratify the appointment of our independent registered public accounting firm for 2020,2021, (iii) approve, on an advisory basis, the compensation of our named executive officers, (iv) approve, on an advisory basis, the frequency of future advisory votes on the compensation of our named executive officers, and (v)(iv) transact such other business as may properly come before the meeting.

Whether or not you plan to attend the virtual meeting, your vote is important. You mayWe encourage you to vote in advance of the meeting by telephone, by Internet or by signing, dating and returning your proxy card by mail. You may also vote by attending the virtual meeting at www.meetingcenter.io/224279586 and voting online. Full instructions are contained in the proxy statement and in the enclosed proxy envelope, by calling the toll free number on the proxy card or via the Internet using the instructions on the proxy card.

We currently intend to hold the annual meeting of stockholders in person. However, we are actively monitoring the coronavirus, orCOVID-19, and are sensitive to the public health and travel concerns that our stockholders may have, as well as protocols that federal, state, and local governments may impose. If it is not possible or advisable to hold the annual meeting of stockholders in person, we will announce alternative arrangements for the meeting as promptly as practicable, which may include switching to a virtual meeting format, or changing the time, date or location of the annual meeting of stockholders. Any such change will be announced via press release and the filing of additional proxy materials with the Securities and Exchange Commission.

We look forward to seeing you at the meeting.

Sincerely yours,

Bruce LucasRichard Widdicombe

Chairman and Chief Executive Officer

We mailed a Notice of Internet Availability of Proxy Materials containing instructions on how to access our proxy statement and annual report on or about April 28, 2020.15, 2021.

This proxy statement and our 20192020 Annual Report are available online at

http://www.edocumentview.com/HRTG.

NOTICE OF 20202021 ANNUAL MEETING

OF STOCKHOLDERS

We currently intend to holdEVEN IF YOU CANNOT ATTEND THE ANNUAL MEETING VIRTUALLY, PLEASE TAKE THE TIME TO PROMPTLY VOTE YOUR SHARES BY CAREFULLY FOLLOWING THE INSTRUCTIONS ON THE PROXY CARD. IF YOU WISH TO VOTE USING A PAPER PROXY CARD, PLEASE SIGN, DATE AND RETURN THE PROXY CARD IN THE RETURN ENVELOPE PROVIDED AS PROMPTLY AS POSSIBLE.YOU CAN REVOKE YOUR PROXY AT ANY TIME BEFORE IT IS EXERCISED.

Important Notice of Internet Availability of Proxy Materials for the 2020 Annual Meeting of Stockholders in person. However, we are actively monitoringto be Held on May 25, 2021: The Proxy Statement for the coronavirus, orCOVID-19, and are sensitive to the public health and travel concerns that our stockholders may have, as well as protocols that federal, state, and local governments may impose. If it is not possible or advisable to hold the 2020 Annual Meeting of Stockholders in person, we will announce alternative arrangementsand the Annual Report on Form 10-K for the meeting as promptly as practicable, which may include switching to a virtual meeting format, or changing the time, date or location of thefiscal year ended December 31, 2020 Annual Meeting. Any such change will be announced via press release and the filing of additional proxy materials with the Securities and Exchange Commission.are available at www.investorvote.com/HRTG.

PROXY SUMMARY

This summary highlights information contained elsewhere in this proxy statement. This summary does not contain all of the information you should consider, and you should read the entire proxy statement carefully before voting.

Items to be Voted on at the 20202021 Annual Meeting of Stockholders

Director Nominees

2020 Engagement and New Executive Compensation Program

2020 Say on Pay Vote and Shareholder Engagement

At the 2020 annual meeting, we held our inaugural Say on Pay vote, and approximately 74% of the votes cast on the proposal were cast against our named executive officers’ compensation. In response to these results, we launched an extensive shareholder outreach effort, in which we actively reached out to 29 institutional investors, representing approximately 52% of the outstanding shares of our common stock. Thirteen of the investors we contacted, representing approximately 26% of the outstanding shares of our common stock, engaged with us. As a result of these engagement efforts, in connection with the appointment of our new CEO, we made substantial changes to our CEO compensation program, as summarized below and in the section “Compensation Discussion and Analysis.”

What We Heard

The shareholders we engaged with primarily expressed dissatisfaction with our prior CEO’s compensation and pointed out the following concerns:

How We Responded

In response to shareholder concerns, we engaged two compensation consulting firms, significantly reduced CEO compensation and meaningfully shifted cash incentive and stock compensation from guaranteed and uncapped to performance-based, with threshold, target and maximum (capped) levels.

The changes to CEO compensation, which are effective beginning with fiscal 2021, include:

New CEO Compensation Program, Effective Beginning Fiscal 2021

New CEO Annual Cash Incentive Criteria, Effective Beginning Fiscal 2021

New CEO Performance-Based Restricted Stock Criteria, Effective Beginning Fiscal 2021

Note: adjusted book value per share growth excludes cumulative dividends declared and accumulated other comprehensive income. Performance is measured over a three-year period.

Prior vs. New CEO Compensation Program

The table below compares the prior CEO compensation program, which expired in 2020, to the new program, which commenced at the beginning of 2021.

Our new CEO was awarded $500,000 of three-year, time-based restricted stock in fiscal 2021 and will be eligible to receive $500,000 time-based equity grants annually in future fiscal years.

Corporate Governance

We are committed to high standards of ethical and business conduct and strong corporate governance practices. This commitment is highlighted by the practices described below.

Proxy Statement for the Annual Meeting of Stockholders of

HERITAGE INSURANCE HOLDINGS, INC.

To Be Held on June 22, 2020May 25, 2021

TABLE OF CONTENTS

HERITAGE INSURANCE HOLDINGS, INC.

2600 McCormick Drive Suite 300

Clearwater, Florida 33759

PROXY STATEMENT

This proxy statement and enclosed proxy card are being furnished commencing on or about April 28, 202015, 2021 in connection with the solicitation of proxies by the Board of Directors of Heritage Insurance Holdings, Inc., a Delaware corporation. In this proxy statement, we refer to Heritage Insurance Holdings, Inc. as the “Company,” “we,” “our” or “us” and the Board of Directors as the “Board.” We are sending the proxy materials because the Board is seeking your permission (or proxy) to vote your shares at the annual meeting of stockholders on your behalf. This proxy statement presents information that is intended to help you in reaching a decision on voting your shares of common stock. Only common stockholders of record at the close of business on April 23, 2020,5, 2021, the record date, are entitled to vote at the meeting, with each share entitled to one vote. We have no other voting securities other than our common stock.

Questions and Answers about Voting and the Annual Meeting

When and where is the Annual Meetingannual meeting being held?

Why are you holding a virtual meeting instead of a physical meeting?

What if I have trouble accessing the annual meeting virtually?

Who can attend the Annual Meeting?annual meeting?

Do I need to register to attend the annual meeting virtually?

Who can vote at the Annual Meeting?annual meeting?

Can I ask questions at the annual meeting?

Will my vote be disclosed to anyone?

What is the quorum required for the meeting to be held?

Can I change my vote after I return my proxy card?

What are the consequences if I choose not to vote on a specific proposal?

What happens if additional matters are presented at the annual meeting?

Annual Meeting Procedures

Admission to the Virtual Annual Meeting

Only stockholders of the Company or their duly authorized proxies may virtually attend the annual meeting. Stockholders may only attend the annual meeting at www.meetingcenter.io/224279586. The password for the meeting is HRTG2021.

The meeting will only be conducted via live audio webcast; there will be no physical meeting location. To participate in the annual meeting, stockholders of record will need the 15-digit control number that appears on your proxy card or the instructions that accompanied the proxy materials. If you would like to attend the virtual meeting and you have your control number, please go to www.meetingcenter.io/224279586 prior to the start of the meeting to log in. Online access to the webcast will open approximately 30 minutes prior to the start of the annual meeting to allow time for our stockholders to log in and test their devices’ audio system.

Beneficial Owners

If your shares are held in a stock brokerage account or by a bank or other nominee, you are considered the beneficial owner of shares held in “street name,” and your broker, bank or nominee is considered the stockholder of record with respect to those shares.

Beneficial owners must register for the annual meeting if they want to virtually attend, ask questions, and/or vote at the annual meeting. They may register for the annual meeting in the following two ways:

Requests for advance registration should be directed to Computershare through either of the following methods:

Participation during the Annual Meeting

Stockholders will have the ability to submit questions during the annual meeting via the annual meeting website at www.meetingcenter.io/224279586. As part of the annual meeting, we will hold a question and answer session, during which we intend to answer questions submitted during the meeting that are pertinent to the meeting matters, as time permits.

Appraisal Rights

Stockholders do not have appraisal rights under Delaware law in connection with the matters to be voted on at the annual meeting.

Stockholder List

You may examine our stockholder list during the annual meeting by following the instructions provided on the meeting website during the annual meeting. The stockholder list will also be available for examination during normal business hours for ten days prior to the annual meeting for any purpose germane to the meeting at our corporate headquarters at 2600 McCormick Drive Suite 300, Clearwater, Florida 33759.

PROPOSALS TO BE VOTED ON

Proposal 1: Election of Directors

Nominees

The size of the Board is currently set at tennine members. Our previous Chairman and Chief Executive Officer, Bruce Lucas, served his last day as an employee and board member of the Company on November 30, 2020. Pursuant to our Bylaws, we appointed Ernie Garateix to fill the resulting vacancy on the Board and appointed Richard Widdicombe to serve as Chairman of the Board, each until the 2021 annual meeting. In addition, James Masiello retired from our Board on March 3, 2021, following which the Board size was decreased to nine directors.

At the annual meeting, the stockholders will elect tennine directors to serve until the 20212022 annual meeting of stockholders or until their respective successors are elected and qualified. Any other vacanciesvacancy occurring after the election may be filled by a majority vote of the remaining directors. In accordance with the Company’s Bylaws, a director appointed to fill a vacancy will be appointed to serve until the next annual meeting of stockholders.

Assuming a quorum is present, the tennine nominees receiving the highest number of affirmative votes of shares entitled to be voted for them will be elected as directors of the Company. Stockholders are not entitled to cumulate votes in the election of directors. All nominees have consented to serve as directors, if elected. If any nominee is unable or declines to serve as a director at the time of the annual meeting, the proxy holders may vote for any nominee designated by the present Board to fill the vacancy. As of the date of this proxy statement, the Board has no reason to believe that any of the director nominees named herein will be unable or unwilling to serve as a director if elected.

The Company believes that its Board, as a whole, should encompass a range of talent, skill, diversity, experience and expertise enabling it to provide sound guidance with respect to the Company’s operations and interests. In addition to considering a candidate’s background, experience and accomplishments, candidates are reviewed in the context of the current composition of the Board and the evolving needs of our business. Although the Company does not have a formal policy with regard to the consideration of diversity in identifying candidates, the Corporate Governance and Nominating Committee strives to nominate candidates with a variety of complementary skills so that, as a group, the Board will possess the appropriate level of talent, skills and expertise to oversee the Company’s business. The Company regularly assesses the size of the Board, whether any vacancies are expected due to retirement or otherwise, and the need for particular expertise on the Board. The Company’s policy is to have at least a majority of our directors qualify as “independent directors” as defined in the rules of the NYSE. Currently, sixfive of our tennine directors are independent. See page 1312 for a further discussion of director independence.

The Corporate Governance and Nominating Committee seeks candidates with strong reputations and experience in areas relevant to the strategy and operations of the Company, particularly in industries and growth segments that the Company serves, as well as key geographic markets where it operates. Each of the director nominees holds or has held senior positions in complex organizations and has operating experience that meets this objective, as described below. In these positions, they have also gained experience in core management skills, such as strategic and financial planning, financial reporting, corporate governance, risk management and leadership development.

The Corporate Governance and Nominating Committee also believes that the nominees, each of whom is a current director, has the experience, expertise, integrity, sound judgment and ability to engage management in a collaborative fashion to collectively comprise an effective Board. In addition, the Corporate Governance and Nominating Committee believes that each of the nominees is committed to devoting significant time and energy to service on the Board and its committees.

The names of the director nominees, their ages as of April 23, 2020,15, 2021, their recent employment or principal occupation, the names of any public companies for which they currently serve as a director or have served as a director within the past five years, and their period of service as a Company director are set forth below.

DIRECTOR NOMINEES

Bruce LucasErnie Garateix. Mr. LucasGarateix has served as our Chief Executive Officer and as a member of our Board since December 2020. Prior to that, he served as our Chief Operating Officer since December 2014. Prior to that, from August 2012 to December 2014, Mr. Garateix served as our Executive Vice President. Prior to joining us, Mr. Garateix served as Vice President for American Integrity Insurance Group beginning in October 2007. Mr. Garateix brings to the Board an in-depth knowledge of the insurance industry gained from his service in senior positions at the Company and his years of leadership experience at insurance carriers.

Richard Widdicombe. Mr. Widdicombe is our Chairman and has served on our Board since we began operations in August 2012. Mr. Lucas has served as our Chairman and CEO since May 2014 and served as our Chairman and Chief Investment Officer from August 2012, to May 2014. Prior to joining the Company, from January 2012 to August 2012, Mr. Lucas served as the Managing Member of IIM Holdings, II, LLC, an investment company. Prior to that, Mr. Lucas served as Chief Executive Officer of Infinity Investment Funds, a hedge fund, from April 2009 to December 2011. Prior to joining Infinity, Mr. Lucas was a restructuring attorney at Weil, Gotshal & Manges LLP. Mr. Lucas brings to the Board a critical link to management’s perspective in board discussions regarding the business and strategic direction of the Company.

Richard Widdicombe. Mr. Widdicombe has served on our Board and as our President since we began operations infrom August 2012. Mr. Widdicombe served as2012 until December 2020. He was previously our Chief Executive Officer from August 2012 to May 2014. Prior to joining the Company, Mr. Widdicombe served as Risk Manager of Homeowners Choice Property & Casualty Insurance Company (NYSE: HCI) from November 2009 to September 2011. Prior to that, Mr. Widdicombe served as President of People’s Trust Insurance Company from July 2007 to February 2009. Mr. Widdicombe brings to the Board anin-depth knowledge of the insurance industry gained from his years of leadership experience at multiple insurance carriers.

Pete Apostolou. Mr. Apostolou has served on our Board since we began operations in August 2012. Mr. Apostolou is the owner of Central ParkingTitle Services, which he founded in 2010.2015. He is also a real estate broker and owner of Alexa Realty of St. Petersburg, which he founded in 2004. Mr. Apostolou also serves as a manager and owner of several other commercial real estate companies.companies in the greater Tampa Bay area. Mr. Apostolou brings to the Board anin-depth knowledge of the Florida commercial and residential real estate market.

Irini Barlas. Ms. Barlas has served on our Board since August 2014.2014 and brings over 20 years of operational and management experience in the financial services sector. Ms. Barlas is the Chief Financial and Operating Officer of Megastar Advisors, LLC, an insurance marketing and training organization, and has served in such role since January 2014. Since February 2010, Ms. Barlas has also served as the Director of Accounting and FinanceChief Financial Officer of Barlas &Chambers,Tax & Financial Group, LLC, a provider of tax, insurance and investment services. Previously, from January 2009 through January 2010, Ms. Barlas was an auditor at Grant Thornton LLP. Ms. Barlas has also held various other management positions in both accounting and operations over the years. Ms. Barlas is a member of the American Institute of Certified Public Accountants and the Florida Institute of Certified Public Accountants. Ms. Barlas has a strong operational background and brings to the Board extensive experience in financial statement preparation and financial reporting and analysis.

Mark Berset. Mr. Berset has 4445 years of experience in the property and casualty insurance industry. Mr. Berset has served as chief executive officer of Comegys Insurance Agency since 1975, as chief executive officer of Alpha Insurance Management since 1993, and as chief executive officer of Strategic Agency Network of Florida, an alliance of insurance agents, since 1997. Mr. Berset alsoco-founded Purpose Employer Solutions, a national payroll company, in 2010 and has served as a director since then. Mr. Berset has alsoco-founded various Florida-based property and casualty insurance companies and served as a board member of United Property & Casualty Insurance Co. until 2007. Mr. Berset serves on the boards of directors of two private companies and previously served on the board of directors of Innovaro, Inc., formerly a software-based consulting company, from 2009 to 2015. Mr. Berset brings to the Board anin-depth knowledge of the insurance industry gained from his years of executive management and leadership experience running insurance agencies andco-founding insurance companies and businesses in related industries.

Steven Martindale. Mr. Martindale has served on our Board since January 2018. Since May 2018, Mr. Martindale has been the president of Smartscor, Inc, a consulting company. Prior to that, Mr. Martindale served as our Chief Financial Officer from May 2016 to January 2018 and as ourCo-Chief Financial Officer from January 2018 to April 2018. Prior to joining the Company, Mr. Martindale served as Chief Financial Officer at People’s Trust Insurance Company, a privately held insurer licensed in the State of Florida, from

September 2013 to May 2016. Prior to People’s Trust, Mr. Martindale was Chief Regulatory Officer for the State of Ohio from April 2011 to September 2013. From August 2008 to September 2013, Mr. Martindale was a partner and consulting

Proposal 2: Ratification of Appointment of Independent Registered Public Accounting Firm

The Audit Committee is directly responsible for the appointment, compensation, retention and oversight of our independent registered public accounting firm. To execute this responsibility, the Audit Committee engages in a comprehensive evaluation of the independent registered public accounting firm’s qualifications, performance and independence and whether the independent registered public accounting firm should be rotated, and considers the advisability and potential impact of selecting a different independent registered public accounting firm.

Plante & Moran, PLLC (“Plante & Moran”) has served as our independent registered public accounting firm since June 2018 and has been appointed by the Audit Committee to continue as our independent registered public accounting firm for the fiscal year ending December 31, 2020.2021. Although ratification is not required by our Bylaws or otherwise, we are submitting the selection of Plante & Moran to our stockholders for ratification because we value our stockholders’ views on our independent registered public accounting firm and as a matter of good corporate governance. In the event that ratification of this selection is not approved by the affirmative vote of the holders of a majority of the shares of common stock of the Company represented at the annual meeting in personvirtually or by proxy and entitled to vote on the item, the Audit Committee and the Board will review the Audit Committee’s future selection of an independent registered public accounting firm, but is not bound by the stockholders’ vote. Even if the selection is ratified, the Audit Committee may, in its discretion, direct the appointment of a different independent registered public accounting firm at any time if it determines that a change would be in the best interests of usthe Company and our stockholders.

Prior to the engagement of Plante & Moran, Grant Thornton LLP (“Grant Thornton”) had served as our independent auditor from November 2013. In June 2018, our Audit Committee approved the dismissal of Grant Thornton and appointed Plante & Moran as our independent registered public accounting firm. Grant Thornton’s audit reports on our financial statements for our prior years did not contain any adverse opinion or disclaimer of opinion, and were not qualified or modified as to uncertainty, audit scope or accounting principles. During the interim period from January 1, 2018 through June 14, 2018, (i) there were no disagreements with Grant Thornton on any matter of accounting principles or practices, financial statement disclosure or auditing scope or procedures that, if not resolved to Grant Thornton’s satisfaction, would have caused Grant Thornton to make reference to the subject matter of the disagreement in connection with its reports and (ii) there were no “reportable events” as defined in Item 304(a)(1)(v) ofRegulation S-K. In June 2018, we filed a Current Report on Form8-K to announce the changes in our independent registered public accounting firms, attaching as an exhibit thereto the letter we requested from Grant Thornton addressed to the SEC stating that Grant Thornton agreed with the statement contained in the Current Report.

Representatives of Plante & Moran will be available via teleconference at the annual meeting. The representatives will have an opportunity to make a statement and will be available to respond to appropriate questions.

Required Vote

The affirmative vote of the holders of a majority of the Company’s common stock present at the annual meeting in personvirtually or by proxy and entitled to vote on this proposal is required to approve the ratification of the appointment of Plante & Moran as the Company’s independent registered public accounting firm for the current fiscal year.

THE BOARD RECOMMENDS A VOTE “FOR” RATIFICATION OF THE APPOINTMENT OF PLANTE & MORAN, PLLC AS THE COMPANY’S INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM FOR THE FISCAL YEAR ENDING DECEMBER 31, 2020.2021.

Proposal 3: Advisory Vote on Executive Compensation

We are providing stockholders an advisory vote on executive compensation, or Say on Pay, as required by the Dodd-Frank Act. The Say on Pay vote is anon-binding vote on the compensation of our named executive officers, as described in this proxy statement in the Compensation Discussion and Analysis, the compensation tables, and the related narrative disclosure. The Dodd-Frank Act requires us to hold the Say on Pay vote at least once every three years.years, and the Company has determined to hold the Say on Pay vote every year.

We encourage stockholders to review the Compensation Discussion and Analysis, the compensation tables, and the related narrative disclosure on pages 18-2217-39 of this proxy statement. As discussed in the Compensation Discussion and Analysis section, we believe that our compensation policies and decisions, particularly with respect to our new 2021 compensation program for our CEO, further our objectives to: (i) reward superior financial and operational performance; (ii) motivate our executive officers to build and grow our business profitably; (iii) align the interests of our executive officers with those of our stockholders; and (iv) enable us to attract, retain and motivate qualified executive officers.

At the 2020 annual meeting, we held our inaugural Say on Pay vote, and approximately 74% of the votes cast on the proposal were cast against our named executive officers’ compensation. In response to these results, we launched an extensive shareholder outreach effort, in which we actively reached out to 29 institutional investors, representing approximately 52% of the outstanding shares of our common stock. Thirteen of the investors we contacted, representing approximately 26% of the outstanding shares of our common stock, engaged with us.

The shareholders we engaged with primarily expressed dissatisfaction with our prior CEO’s compensation. As we value the feedback provided by these investors, the Board took action to specifically address their concerns and, in connection with the appointment of our new CEO, we made substantial changes to our CEO compensation program, as summarized in the section “Compensation Discussion and Analysis,” while still maintaining a CEO compensation program focused on retaining and motivating our CEO. The Compensation Committee believes that the CEO compensation changes for 2021, as summarized below, reflect our Board’s ongoing commitment to shareholder engagement and responsiveness.

The changes to CEO compensation, which are effective beginning with fiscal 2021, include:

We believe that our executive compensation program strikes the appropriate balance between utilizing responsible, measured pay practices and effectively incentivizing our executives to dedicate themselves fully to value creation for our stockholders.

On the basis of the Compensation Discussion and Analysis, the compensation tables, and the related narrative disclosure found within this proxy statement, we are requesting that our stockholders vote on the following resolution:

“RESOLVED, that the stockholders of Heritage Insurance Holdings, Inc. (“Heritage”Heritage”) approve, on an advisory basis, the compensation of Heritage’s named executive officers, as described in the Compensation

Discussion and Analysis section, the tabular disclosure regarding such compensation, and the accompanying narrative disclosure, set forth in Heritage’s 20202021 Annual Meeting proxy statement.”

Although this Say on Pay vote on executive compensation isnon-binding, the Board and the Compensation Committee will review the results of the vote and will take into account the outcome of the vote when determining future executive compensation arrangements.

Required Vote

The approval of the Say on Pay proposal requires the affirmative vote of a majority of the shares of the Company’s common stock represented at the annual meeting and entitled to vote thereon.

THE BOARD RECOMMENDS A VOTE “FOR” ADOPTION OF THE RESOLUTION APPROVING THE COMPENSATION OF OUR NAMED EXECUTIVE OFFICERS, AS DESCRIBED IN THE COMPENSATION DISCUSSION AND ANALYSIS SECTION.

Proposal 4: Advisory Vote on Frequency of Future Advisory Votes on Executive Compensation

The Dodd-Frank Act requires us to provide our stockholders with the opportunity to vote, on a nonbinding, advisory basis, for their preference as to whether future Say on Pay advisory votes on the compensation of our named executive officers should occur every one, two or three years. You have the option to vote for any of the three options, or to abstain from casting a vote. We are required to hold a vote on the frequency of Say on Pay proposals every six years.

After careful consideration, our Board recommends that we conduct an advisory vote on executive compensation annually. Our Board believes that a frequency of every year for the Say on Pay vote on executive compensation is the best approach for the Company and our stockholders. An annual advisory vote provides more frequent stockholder feedback to our Board and the Compensation Committee regarding our executive compensation programs and policies. Our Board and Compensation Committee intend to consider this advisory vote as part of the design of our executive compensation programs and communication of such programs to our stockholders.

Required Vote

The frequency that receives the most votes will be considered to be the frequency favored by stockholders.

THE BOARD RECOMMENDS A VOTE “FOR” A FREQUENCY OF “ONE YEAR” FOR FUTURENON-BINDING STOCKHOLDER VOTES ON COMPENSATION OF OUR NAMED EXECUTIVE OFFICERS.

The Audit Committee is responsible for, among other things, assisting the Board in its oversight of:

Compensation Committee. Messrs. Pappas and Vattamattam and Ms. Barlas and Messrs. Masiello and Pappas serve on the Compensation Committee. Mr. Masiello served on the Compensation Committee, as its chairman, during all of 2020 until his retirement from the Board in February 2021. Mr. Vattamattam now serves as the chairman of ourthe Compensation Committee, and subject to hisre-election, election, the Board has selected Mr. MasielloVattamattam to continue as chairman of the Compensation Committee. The Compensation Committee is composed ofnon-employee directors, each of whom is independent as required by the applicable listing standards of the NYSE, including the heightened independence requirements specific to compensation committee members. During 2019,2020, the Compensation Committee held one meetingfive meetings and also acted by written consent in lieu of two meetings.

The Compensation Committee is responsible for, among other things:

Compensation Committee Interlocks and Insider Participation. None of the members of the Compensation Committee was at any time during 20192020 or at any other time an officer or employee of our Company. None of our executive officers serves as a member of the board of directors or compensation committee of any other entity that has one or more executive officers serving as a member of our Board or Compensation Committee.

Corporate Governance and Nominating Committee. Messrs. Masiello, Pappas, Apostolou, and Walvekar serve on the Corporate Governance and Nominating Committee. Mr. Masiello served on the Corporate Governance and Nominating Committee during all of 2020. Mr. Pappas serves as the chairman of our Corporate Governance and Nominating Committee and, subject to hisre-election, the Board has selected Mr. Pappas to continue as chairman of the Corporate Governance and Nominating Committee. The Corporate Governance and Nominating Committee is composed of independentnon-employee directors, each of whom is independent as required by the applicable listing standards of the NYSE. During 2019,2020, the Corporate Governance and Nominating Committee held one meeting and also acted by written consent in lieu of a meeting.

The Corporate Governance and Nominating Committee is responsible for, among other things:

In evaluating and determining whether to nominate a candidate for a position on our Board, the Corporate Governance and Nominating Committee will consider the candidate’s professional ethics and values, relevant management experience and a commitment to enhancing stockholder value. We regularly assess the size of the Board, whether any vacancies are expected due to retirement or otherwise, and the need for particular expertise on the Board. Candidates may come to the attention of the Corporate Governance and Nominating Committee from current Board members, stockholders, professional search firms, officers or other persons. The Corporate Governance and Nominating Committee will review all candidates in the same manner regardless of the source of recommendation, including from stockholders.

The Corporate Governance and Nominating Committee will consider stockholder recommendations of candidates when the recommendations are properly submitted in accordance with our Bylaws. Any stockholder recommendations which are submitted under the criteria summarized above should include the candidate’s name and qualifications for Board membership and should be addressed to our Corporate Secretary.

For purposes of potential nominees to be considered at the 20212022 annual stockholders’ meeting, the Corporate Secretary must receive this information no earlier than February 22, 2021January 25, 2022 and no later than the close of business on MarchFebruary 24, 20212022 in accordance with the procedures in the Bylaws. The notice must set forth the candidate’s name, age, business address, residence address, principal occupation or employment, the number of shares beneficially owned by the candidate and information that would be required to solicit a proxy under federal securities law. In addition, the notice must include the stockholder’s name, address and the number of shares beneficially owned (and the period they have been held).

In 2019,2020, we did not engage a third party to identify, evaluate or assist in identifying potential nominees for director.

Director Independence

There are no family relationships among any of our executive officers or directors. Our Board has affirmatively determined that each of Messrs. Apostolou, Masiello, Pappas, Vattamattam and Walvekar and Ms. Barlas is an “independent director,” as defined under the rules of the NYSE. In making the independence determination, the Board considered the current and prior relationships that eachnon-employee director has with the Company and all other facts and circumstances that the Board deemed relevant. Messrs. Lucas and Widdicombe areMr. Garateix is not independent as they are executive officershe is our Chief Executive Officer. Mr. Widdicombe, as a former President of the Company.Company, and Mr. Martindale, as a former CFO of the Company isuntil April 2018, are not independent.considered independent under the rules of the NYSE. With respect to Mr. Berset, the Board does not consider him to be independent given his affiliation with a third-party insurance agency that has provided services to, and received payments from, the Company.

Code of Business Conduct and Ethics

We have adopted a Code of Business Conduct and Ethics (the “Code“Code of Ethics”Ethics”) that applies to all of our employees, including our Chief Executive Officer (“CEO”), our Chief Financial Officer (“CFO”) and our Chief Accounting Officer. The Code of Ethics is available at www.heritagepci.com on the “Investors” page listed as “Governance Documents” under the heading “Corporate Governance.”

Only the Board or an appointed committee may grant a waiver of the Code of Ethics for our executive officers or directors, and any such waiver will be disclosed to the extent required by law or the listing requirements of the NYSE. We intend to provide disclosure of any amendments or waivers of our Code of Ethics on our website within four business days following the date of the amendment or waiver.

Governance Documents

Current copies of the Company’s Audit Committee, Compensation Committee and Corporate Governance and Nominating Committee charters are available at www.heritagepci.com on the “Investors” page listed as “Governance Documents” under the heading “Corporate Governance.” In addition, the Board has adopted corporate governance guidelines, which are available at www.heritagepci.com on the “Investors” page listed as “Governance Documents” under the heading “Corporate Governance.” Information on, or accessible through, our website is not a part of, or incorporated by reference into, this proxy statement.

Communications with Directors

The Board has established a process to receive communications from stockholders. Stockholders and other interested parties may contact any member (or all members) of the Board, or thenon-management directors as a group, any Board committee or any chair of any such committee by mail. To communicate with the Board, any individual directors or any group or committee of directors, correspondence should be addressed to the Board or any such individual directors or group or committee of directors by either name or title. All such correspondence should be sent c/o Kirk Lusk, Chief Financial Officer, Heritage Insurance Holdings, 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759.

All communications received as set forth in the preceding paragraph will be opened by the Corporate Secretary for the sole purpose of determining whether the contents represent a message to our directors. The Corporate Secretary will forward copies of all correspondence that, in the opinion of the Corporate Secretary, deals with the functions of the Board or its committees or that he otherwise determines requires the attention of any member, group or committee of the Board.

Attendance at Annual Meeting

Directors are encouraged, but not required, to attend our annual stockholders’ meeting. In 2019, 42020, six directors attended the annual stockholders’ meeting.

EXECUTIVE OFFICERS

The names of the executive officers of the Company and their ages, titles and biographies are set forth below.

Bruce LucasErnie Garateix, 48,49, is being nominated for the position of director of the Company. See “Director Nominees” for a discussion of Mr. Lucas’ business experience.

Richard Widdicombe, 61, is being nominated for the position of director of the Company. See “Director Nominees” for a discussion of Mr. Widdicombe’sGarateix’s business experience.

Kirk Lusk, 59,60, has served as our Chief Financial Officer since April 2018 and as ourCo-Chief Financial Officer since January 2018. Prior to joining us, from January 2013 to February 2018, Mr. Lusk served as Chief Financial Officer of Narragansett Bay Insurance Company (“NBIC”), which was acquired by us in November 2017 in connection with the acquisition of NBIC Holdings, Inc., the parent company of NBIC. Prior to that, Mr. Lusk served as International Chief Financial Officer of Aetna, Inc. from 2008 through 2012, Chief Financial Officer of Alea Group Holdings Bermuda Ltd. from 2005 through 2008 and Chief Financial Officer of GE ERC’s Global Casualty and GE Capital Auto Warranty Services from 1998 through 2004.

Ernie Garateix, 48, has served as our Chief Operating Officer since December 2014. Prior to that, from August 2012 to December 2014, Mr. Garateix served as our Executive Vice President. Prior to joining us, Mr. Garateix served as Vice President for American Integrity Insurance Group beginning in October 2007.

Sharon Binnun, 58,59, has served as our Chief Accounting Officer since May 2016. Prior to that, she served as our Executive Vice President of Finance beginning in November 2014. Prior to joining us, Ms. Binnun served as the Executive Vice President of Cypress Property Insurance Company from July 2013 to August 2014. Prior to that, Ms. Binnun served as the Chief Financial Officer of Citizens Property Insurance Corporation from February 2007 to July 2013. Ms. Binnun’s prior employment includes Deputy Insurance Commissioner in Florida as well as a career at Deloitte & Touche. Ms. Binnun is a certified public accountant in the State of Florida.

Joseph Peiso, 61, has served as our Vice President of Compliance since May 2014 and previously served as our Controller from September 2012 to May 2014. Prior to joining us, Mr. Peiso served as Chief Financial Officer of Sunz Insurance Holdings, LLC from September 2011 to August 2012. Prior to that, Mr. Peiso served as Chief Financial Officer of United Insurance Holdings Corporation (NASDAQ: UIHC) from January 2010 to August 2011. From June 2004 to December 2009, Mr. Peiso served as Managing Member of Sarasota Bay Insurance Managers, LLC. Mr. Peiso is a certified public accountant in the State of Florida.

Tim Moura 47,, 48, has served as the President of our subsidiary company, Narragansett Bay Insurance Company (“NBIC”),NBIC, since January 2018. Prior to joining us, from February 2014 to January 2018, Mr. Moura served as Senior Vice President of NBIC, which we acquired in November 2017, from February 2014 until January 2018. Prior to that, Mr. Moura served as Vice President of Tower Group Companies from 2010 through 2013, Regional Vice President for OneBeacon Insurance Group from 2004 to 2006 and in various management roles at MetLife Auto & Home from 1995 to 2004. Mr. Moura has 25 years of industry experience, serving in leadership positions with both national and regional insurance carriers.

Tim Johns, 65, has served as the President of our subsidiary company, Zephyr Insurance Company, since April 2018. Prior to joining us, from June 2011 to July 2017, Mr. Johns served as a health insurance executive, including as Executive Vice President and Chief Consumer Officer, of Hawaii Medical Service Association (Blue Cross Blue Shield of Hawaii). Mr. Johns has also served as a director of Hawaiian Electric Co., Inc. since February 2005 and as trustee and/or director of private real estate-related organizations and non-profit and charitable foundations.

STOCK OWNERSHIP

Security Ownership of Certain Beneficial Owners and Management

The following table sets forth certain information regarding the beneficial ownership of our common stock as of April 23, 20205, 2021 (except as indicated below) by:

Unless otherwise indicated, the address of each beneficial owner listed below is c/o Heritage Insurance Holdings, Inc., 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759.

COMPENSATION DISCUSSION AND ANALYSIS

New Developments

2020 Say on Pay Vote and Shareholder Engagement

At the 2020 annual meeting, we held our inaugural Say on Pay vote, and approximately 74% of the votes cast on the proposal were cast against our named executive officers’ compensation. In response to these results, we launched an extensive shareholder outreach effort, in which we actively reached out to 29 institutional investors, representing approximately 52% of the outstanding shares of our common stock. Thirteen of the investors we contacted, representing approximately 26% of the outstanding shares of our common stock, engaged with us. As a result of these engagement efforts, in connection with the appointment of our new CEO, we made substantial changes to our CEO compensation program, as summarized below and in the section “Compensation Discussion and Analysis.”

What We Heard

The shareholders we engaged with primarily expressed dissatisfaction with our prior CEO’s compensation and pointed out the following concerns:

How We Responded

In response to shareholder concerns, we engaged two compensation consulting firms, significantly reduced CEO compensation and meaningfully shifted cash incentive and stock compensation from guaranteed and uncapped to performance-based, with threshold, target and maximum (capped) levels.

The changes to CEO compensation, which are effective beginning with fiscal 2021, include:

New CEO Compensation Program, Effective Beginning Fiscal 2021

New CEO Annual Cash Incentive Criteria, Effective Beginning Fiscal 2021

New CEO Performance-Based Restricted Stock Criteria, Effective Beginning Fiscal 2021

Note: adjusted book value per share growth excludes cumulative dividends declared and accumulated other comprehensive income. Performance is measured over a three-year period.

Prior vs. New CEO Compensation Program

The table below compares the prior CEO compensation program, which expired in 2020, to the new program, which commenced at the beginning of 2021.

Our new CEO was awarded $500,000 of three-year, time-based restricted stock in fiscal 2021 and will be eligible to receive $500,000 time-based equity grants annually in future fiscal years.

General Overview

This Compensation Discussion and Analysis outlines our compensation philosophy, describes the process for setting compensation of our named executive officers and outlines the elements of our executive compensation program and decisions in 2019.2020. For 2019,2020, our named executive officers (“NEOs”) are:

Mr. Garateix was appointed Chief Executive Officer effective December 1, 2020 following Mr. Lucas’ departure from the Company. We retained Mr. Lucas to serve as a consultant through 2021. In April 2021, we

provided Mr. Lucas with written notice that we would not renew his consulting agreement after 2021. Effective December 30, 2020, Mr. Widdicombe left his position as President and was appointed Chairman of the Board.

Compensation Philosophy

Our compensation philosophy is based onpay-for-performance principles. Our executive compensation program is designed to accomplish each of the following goals:

20192020 Performance Highlights

Key achievements for 20192020 include:

has instead drawn information from general experience of the insurance industry and comparable companies. As described in more detail above under the heading “—New Developments” and below, following our 2020 annual meeting, we conducted extensive shareholder engagement on executive compensation matters, engaged two compensation consulting firms, benchmarked CEO compensation against market peers and developed a new CEO compensation program responsive to the concerns of our shareholders. We considered a variety of factors in formulating a compensation package for our CEO, including an analysis of peer companies’ CEO compensation, as discussed below under the heading “—Peer Companies.”

Each NEO has, or with respect to Mr. Lucas and Mr. Widdicombe who are no longer employees of the Company, had, an employment agreement which provides for a minimum annual base salary and, except for Mr. Johns, annual cash and/or equity incentive awards. Mr. Garateix entered into a new employment agreement with the Company subsequent to his appointment as CEO, replacing the employment agreement he had as COO. As such, significant portions of our NEO’sNEOs’ compensation are determined based on the provisions of their existing employment agreements, which, with respect to Messrs. Lucas, Widdicombe and Garateix, expire at the end of 2020.agreements.

With respect to annual cash incentives, each year, including in 2020, the Compensation Committee reviews our EBITDA performance for the fiscal year and the individual contributions of eachthe applicable NEO, and determines the size of the EBITDA cash incentive award pool and the allocation of the pool to ourthe applicable NEOs, as more fully described below. Mr. Johns’ annual cash incentive is based on the performance results for Zephyr. Our CEO provides the Compensation Committee with recommendations regarding the allocation of the pool to our other executive officers, subject to the requirements of any individual employment agreement. Beginning in 2021, our CEO and CFO will not participate in the EBITDA cash incentive award pool, but instead will be eligible for annual performance-based cash incentives with target, threshold and maximum (capped) levels tied to company performance and qualitative individual performance.

Peer Companies

TheFor compensation related to fiscal year 2020, the Compensation Committee did not formally determine or utilize a peer group in setting 2019 compensation. However, when evaluating the Company’s performance and compensation levels, the Compensation Committee does consider the performance and compensation levels of public companies based in Florida that are engaged in the residential property insurance business, including FedNat Holding Company, United Insurance Holdings Corp, HCI Group Inc. and Universal Insurance Holdings, Inc.group.

Although the Compensation Committee believes a comparison of compensation and performance data can be useful, the Compensation Committee does not believe that any comparison group company, whose composition is based solely on our industry classification, revenues, net income and/or market capitalization, is fully reflective of the markets in which we compete for talent. Consequently, the Compensation Committee does not set the executives’ target total direct compensation, or any of the target components of such compensation, at any specific percentile of the comparison group.

The Compensation Committee believes that overreliance on market capitalization and revenues can be misleading, as the former is highly influenced by the Company’s and its peers’ trading multiples and consequently does not necessarily reflect the underlying size, breadth and complexity of our organization, while the latter is disproportionately impacted by our large reinsurance spend, which is accounted for as a reduction to gross revenues. As a result, the Compensation Committee generally believes annual gross premiums written represent a more useful metric when selecting other insurance companies for benchmarking purposes.

Following our shareholder engagement process, we began benchmarking CEO and executive compensation against the companies listed in the table below. While this benchmarking exercise did not impact fiscal 2020 compensation given the aforementioned existing employment agreements, it did influence Mr. Garateix’s and Mr. Lusk’s new employment agreements, which are effective beginning in 2021.

Elements of Executive Compensation Program

OurFor 2020, our executive compensation program consistsconsisted of three primary elements:

Base Salary – We provide base salaries, which are intended to be generally competitive with salaries of similarly-situated executives at comparable companies and are based on the executive officer’s role and responsibilities, individual job performance and experience. The base salaries for our named executive officers were initially set pursuant to their respective employment agreements.

For a description of Mr. Garateix’s new employment agreement, please see the section “Executive Compensation—Employment and Separation Agreements.”

20192020 Executive Compensation Decisions

Consistent with historical practice, for 2019,For 2020, the Compensation Committee approved an EBITDA cash incentive pool equalof $1.8 million, of which $1,082,520 was allocated to 8.5% of our 2019 EBITDA, resulting in a 2019 EBITDA cash incentive pool of $5,540,000. The Compensation Committee awarded the NEOs an aggregate of $2,975,000 of the total pool(other than Mr. Johns) as discussed below. The Compensation Committee deferred the allocation of $1.5$1.6 million of the 2019 cash incentive pool, which as of the date of this proxy statement has not been allocated or paid.was paid to Bruce Lucas in July 2020. The Compensation Committee’s 20192020 executive compensation decisions for each of our named executive officers, which in some cases are based in large part on the terms of each named executive officer’s employment agreement, are discussed below.

For purposes of calculating the cash incentive pool, EBITDA is defined as reported earnings excluding interest, taxes, depreciation, and amortization, as well as any incentive cash compensation accrual recorded on the Company’s books.

Bruce Lucas

Base Salary – The Lucas Amended Agreement (defined below) provides, which was terminated in November 2020 when Mr. Lucas’ employment as Chief Executive Officer and Chairman of the Board ended, provided for an initial base annual salary of $2.0 million commencing in 2016. As provided for in the Lucas Amended Agreement, in 2019,2020, the Compensation Committee approved a 5% increase in Mr. Lucas’ base salary reflecting cost of living and inflation-based adjustments.

Annual Cash Incentive Award – Pursuant to the Lucas Amended Agreement, for 2019, Mr. Lucas was entitled to an (i) incentive of $1.75 million, subject to our achievement of at least $50 million in EBITDA for

Compensation Committee approved an annual cash incentive for Mr. Garateix from the EBITDA pool of $750,000. In making its determination, the Compensation Committee considered Mr. Garateix’s individual contributions to the Company, including his oversight of systems, processes, and personnel and his efforts in enhancing the Company’s business intelligence capabilities. The Prior Garateix Agreement was replaced with a new employment agreement in January 2021, as described below and under the section “Executive Compensation—Employment and Separation Agreements”.

New Garateix Employment Agreement

Base Salary – In January 2021, we entered into a new employment agreement with Mr. Garateix in connection with his appointment as Chief Executive Officer (the “Garateix Agreement”) which replaced and terminated the Prior Garateix Agreement. The Garateix Agreement provides for an annual base salary of $1.0 million.

Annual Cash Incentive Award – Pursuant to the Garateix Agreement, Mr. Garateix will receive an annual cash incentive with a threshold opportunity of $500,000, a target opportunity of $1.0 million, and a maximum opportunity of $1.5 million based on performance criteria included in the Company’s executive incentive compensation program.

Annual Long-Term Incentive Awards – Pursuant to the Garateix Agreement, Mr. Garateix is eligible to receive an annual time-based restricted stock award with a value of $500,000, which shares will vest in three equal annual installments, and an annual performance based restricted stock award with a threshold opportunity of $250,000, a target opportunity of $500,000, and a maximum opportunity of $1.0 million, which shares will vest based on performance criteria included in the Company’s executive incentive compensation program.

For further description of the Garateix Agreement, please see the sections “Executive Compensation—Employment and Separation Agreements” and “Executive Compensation—Estimated Payments Following Termination or Change in Control.”

Kirk Lusk

Prior Lusk Employment Agreement

Base Salary – The Prior Lusk Agreement (defined below) provides for an initial base annual salary of $850,000. Mr. Lusk did not receive a salary increase in 2019. In early 2020, the Compensation Committee determined to increase Mr. Lusk’s base salary by $100,000 to be more in line with market.

Annual Cash Incentive Award – Pursuant to the Prior Lusk Agreement, for 2019,2020, Mr. Lusk was entitled to a cash incentive under the Omnibus Incentive Plan of up to $500,000, subject to the Company’s achievement of a consolidated combined ratio that is below 91 for the preceding calendar year. The Company’s 20192020 consolidated combined ratio was at or above 91. As a result, Mr. Lusk did not receive a cash incentive under his employment agreement. The Compensation Committee awardedthe Prior Lusk Agreement. Mr. Lusk $50,000received an allocation of $75,000 from the 20192020 EBITDA incentive pool.

New Lusk Employment Agreement

Base Salary – In April 2021, we entered into a new employment agreement with Mr. Lusk (the “Lusk Agreement”) which replaced and terminated the Prior Lusk Agreement. The Lusk Agreement provides for an annual base salary of $950,000.

Annual Cash Incentive Award – Pursuant to the Lusk Agreement, Mr. Lusk will receive an annual cash incentive with a threshold opportunity of $150,000, a target opportunity of $250,000, and a maximum opportunity of $350,000 based on performance criteria included in the Company’s executive incentive compensation program.

Annual Long-Term Incentive Awards – Pursuant to the Lusk Agreement, Mr. Lusk is eligible to receive an annual time-based restricted stock award with a value of $150,000, which shares will vest in three equal annual installments, and an annual performance based restricted stock award with a threshold opportunity of $100,000, a target opportunity of $200,000, and a maximum opportunity of $300,000, which shares will vest based on performance criteria included in the Company’s executive incentive compensation program.

For further description of the Lusk Agreement, please see the sections “Executive Compensation—Employment and Separation Agreements” and “Executive Compensation—Estimated Payments Following Termination or Change in Control.”

Richard Widdicombe

Base Salary – The Prior Widdicombe Amended Agreement (defined below) provides, which was terminated in November 2020 when Mr. Widdicombe left his position as President, provided for an initial base annual salary of $1.75 million commencing in 2016. Mr. Widdicombe did not receive a salary increase in 2019.2020.

Annual Cash Incentive Award – Pursuant to the Prior Widdicombe Amended Agreement, for 2019,2020, Mr. Widdicombe was entitled to a cash incentive of $375,000, subject to our achievement of at least $50 million in EBITDA for 2019, and an annual cash incentive from our EBITDA incentive pool with a target amount of $375,000. In 2019,Given that Mr. Widdicombe left his position as President in December 2020, he did not receive a payout under the Compensation Committee approved a total annual cash incentive for Mr.plan. Rather, he received as severance (i) payment of his minimum 2020 annual bonus of $375,000 and (ii) a non-renewal payment of $1,928,990 per the Prior Widdicombe of $750,000,Agreement (defined below), as well as other payments and benefits which representsare further described below under the $375,000 cash incentive when the Company achieved at least $50 million in EBITDA for 2019, plus $375,000 from the EBITDA incentive pool.section “Executive Compensation—Employment and Separation Agreements”.

Ernie GarateixTim Moura

Base Salary – The GarateixMoura Agreement (defined below) provides for an initialannual base annual salary of $750,000$850,000 commencing in 2016. Mr. Garateix did not receive a salary increase in 2019.2018. In mid 2020, the Compensation Committee determined to increase Mr. Garateix’sMoura’s base salary by $100,000 to be more in line with market.

Annual Cash Incentive Award – Pursuant to the Garateix Agreement, for 2019, Mr. Garateix was entitled to an annual cash incentive from our EBITDA cash incentive pool of up to $100,000. In 2019, the Compensation Committee approved an annual cash incentive for Mr. Garateix from the EBITDA pool of $500,000. In making its determination, the Compensation Committee considered Mr. Garateix’s individual contributions to the Company, including his oversight of systems, processes, and personnel and his efforts in enhancing the Company’s business intelligence capabilities.

Annual Cash Incentive Award – Pursuant to the Binnun Agreement, Ms. Binnun is eligible for an annual cash discretionary incentive of up to $60,000 or greater based on the Board’s approval. In 2020, Ms. Binnun received an annual cash discretionary incentive of $50,000.

Severance and Change of Control Agreements

Our named executive officers are not party to any separate severance or change of control agreements. As described below under “Executive Compensation—Employment Agreements and—Estimated Payments Following Termination or Change in Control”, our named executive officers aremay be entitled to certain severance and change of control payments and benefits pursuant to their employment agreements.

Mr. Lucas and Mr. Widdicombe received severance payments upon the termination of their employment with the Company pursuant to the terms of their respective separation agreements. See “Executive Compensation—Employment Agreements and—Estimated Payments Following Termination or Change in Control” below for a description of the amounts paid.

Employee Benefits

Our named executive officers participate in other employee benefit plans generally available to all employees on the same terms, such as medical, dental, life, disability insurance programs and a 401(k) plan, except that the Company provides additional life and disability insurance benefits to Messrs. Lucas, Widdicombe, Garateix and Lusk.Lusk and, until the termination of their employment during 2020, to Messrs. Lucas and Widdicombe. These amounts are included in the “All Other Compensation” column of the Summary Compensation Table and described in a footnote. In addition, in 2019,2020, we provided matching contributions to the 401(k) accounts of all our employees, including our named executive officers, equal to 100% of the first 3% of each employee’s contribution, and 50% of each employee’s next 2% of contribution, subject to applicable limitations. In addition, Messrs. Lucas and Garateix each received an automobile allowance during 2019.2020. We do not provide our named executive officers with any other material perquisites or similar personal benefits.

Hedging

The Company does not have a specific policy that prohibits hedging transactions by our directors, executive officers, and employees, however our insider trading policy requirespre-clearance from our Chief Financial Officer prior to such transactions.

COMPENSATION COMMITTEE REPORT

The Compensation Committee has reviewed and discussed the disclosure set forth above under the heading “Compensation Discussion and Analysis” with management and, based on such review and discussions, it has recommended to the Board that the “Compensation Discussion and Analysis” be included in this proxy statement.

Notwithstanding anything to the contrary set forth in any of our previous filings under the Securities Act of 1933, as amended, or the Exchange Act that might incorporate future filings, including this proxy statement, in whole or in part, the Compensation Committee Report above shall not be incorporated by reference into this proxy statementstatement..

Respectfully submitted by the Compensation Committee of the Board,

The Compensation Committee

Joseph Vattamattam, Chair

Irini Barlas

James Masiello

Nicholas Pappas

April 3, 2020March 23, 2021

EXECUTIVE COMPENSATION

Summary Compensation Table

The following Summary Compensation Table discloses the compensation information for fiscal years 2017, 2018, and 2019of our NEOs for our NEOs.2020 fiscal year. Certain information regarding 20192020 compensation is provided in the narrative sections following the Summary Compensation Table.

In connection with his departure, the Company and Mr. Lucas entered into an amended and restated employment agreementa Separation Agreement effective December 1, 2020 (the “Lucas Separation Agreement”). Pursuant to the Lucas Separation Agreement, Mr. Lucas’ Amended and Restated Employment Agreement dated November 4, 2015 (the “Terminated Lucas Agreement”) with us to serve as our Chief Executive Officer until December 31, 2020. was terminated.

The Terminated Lucas Amended Agreement providesprovided for (i) an annual base salary of $2.0 million, commencing on January 1, 2016 (subject to annual cost of living and inflation-based adjustments), (ii) a cash incentive under our Omnibus Incentive Plan of $1.75 million for each calendar year, beginning in 2016, subject to the Company’s achievement of at least $50 million in EBITDA for such year and (iii) an annual cash incentive under the Company’s EBITDA

Pursuant to the terms of the Widdicombe Separation Agreement, Mr. Widdicombe is entitled to (i) payment of his minimum 2020 annual bonus of $375,000, (ii) a non-renewal payment of $1,928,990 per the Prior Widdicombe Agreement, (iii) $129,867 in effect onexchange for agreeing not to serve as an employee (through November 30, 2021) for any business that writes the change of control date, (ii) his annual incentives in amounts no less than those paidsame insurance products in the preceding 12 monthsstates in which the Company sells insurance products as of the date of the Widdicombe Separation Agreement, (iv) payment for three weeks of accrued and (iii)unused vacation time and (v) payment by the Company of COBRA continuation premiums for 18 months. The Widdicombe Separation Agreement also provides for customary confidentiality, non-disclosure and non-disparagement covenants, an agreement not to solicit any employee benefits as in effect onof the change of control date.

UponCompany for a termination of employment for any reason, Mr. Lucas would continue to be subject tonon-solicitation andnon-competition restrictive covenants for periodsperiod of one year, an agreement to indemnify Mr. Widdicombe for actions taken while he was an employee, and two years, respectively, following such termination.a mutual release of claims.

Mr. Lusk’s Prior Employment Agreement

Effective January 30, 2018,In April 2021, Mr. Lusk entered into anand the Company terminated the employment agreement, as amended October 7, 2019 (the “Lusk“Prior Lusk Agreement”), and entered into the Lusk Agreement with us to serve as Chief Financial Officer of the Company until terminated. TheCompany. Under the Prior Lusk Agreement, provides forMr. Lusk received (i) an annual base salary of $850,000, (ii) a discretionary annual cash incentive of up to $50,000, and (iii) an incentive under the Omnibus Incentive Plan of up to $500,000, subject to the Company’s achievement of a consolidated combined ratio that is below 91 for the preceding calendar year. In addition, in connection with entering into the Prior Lusk Agreement, Mr. Lusk received a grant of 75,000 shares of restricted stock, which vest in equal annual installments of 15,000 shares beginning on January 31, 2019. Mr. Lusk also receives medical, dental, prescription and disability insurance coverage, a monthly housing allowance of $3,500, and reimbursement of reasonable travel expenses.

Mr. Lusk would be entitled to his base salary that is accrued but unpaid, and accrued and unused paid time off for 180 days following the termination date, in the event he is terminated by us without “Cause,” which is defined as occurring upon (i) a felony conviction, (ii) an act of fraud upon the Company, (iii) the willful refusal or gross neglect to perform the duties reasonably assigned, (iv) the breach ofnon-compete,non-solicit, ornon-disclosure obligations, (v) a breach of the employment agreement or (vi) any fraud, breach of fiduciary duty, gross negligence, embezzlement or misappropriation against the Company.

Upon a termination of employment for any reason, Mr. WiddicombeLusk would continue to be subject toa one-year post-employment non-solicitation restrictive andcovenant. Upon a termination of employment for any reason other than an involuntary termination or his voluntary termination for good reason, Mr. Lusk would be subject to a one-year post-employment non-competition restrictive restrictive covenants for periods of one year and two years, respectively, following such termination.covenant.

Tim Moura’s Employment Agreement

Effective February 3, 2014, Mr. Moura entered into an employment agreement, as amended January 1, 2018 (the “Moura Agreement”), with NBIC Service Company, Inc., a subsidiary of the Company, to serve as President of NBIC. The Moura Agreement provides for (i) an annual base salary of $850,000 commencing on January 1, 2018, (ii) an annual cash discretionary incentive of up to $50,000 based on the Board’s approval of the EBITDA incentive pool and Mr. Moura’s performance during the calendar year, and (iii) a cash incentive under the Omnibus Incentive Plan based on NBIC’s annual gross premiums written and combined ratio. In connection with entering into the amendment to the Moura Agreement, Mr. Moura received a grant of 50,000 shares of restricted stock, which vest in equal annual installments of 10,000 shares beginning on January 1, 2019.

Mr. Moura is entitled to24-months’ notice prior to termination by us without “Cause” or for “Good Reason.” In such case, he would be entitled to his cash and share based compensation for the 24 months. “Cause” is defined as (i) the conviction of a felony, (ii) an act of fraud against the Company, (iii) a material breach of the employment agreementMoura Agreement or the willful refusal or gross neglect to perform the duties reasonably assigned, or (iv) the breach of hisnon-compete,non-solicit, ornon-disclosure obligations which results in a material adverse effect on the Company. “Good Reason” is defined as (i) a material diminution in duties, (ii) failure to pay Mr. Moura amounts owed under the agreement,Moura Agreement, (iii) relocation of NBIC’s principal location outside a certain radius, or (v) Mr. Moura’s failure to retain his position at a potential successor to the Company.

If Mr. Moura dies during the term of the Moura Agreement, his estate would be entitled to receive accrued but unpaid base salary, time off, and any other benefits payable through the date of his death.

Mr. Moura may resign upon giving no less than 90 days’ notice.

If Mr. Moura becomes unable to perform substantially his duties for a consecutive period of 120 days, then the Company may terminate him with notice.

Upon a termination of employment for any reason, Mr. Moura would continue to be subject tonon-solicitation andnon-competition restrictive covenants for two years following such termination.

Tim Johns’ Employment Agreement

Effective April 2, 2018, Mr. Johns entered into an employment agreement with Zephyr Insurance Company, Inc. (“Zephyr”), a subsidiary of the Company (the “Johns Agreement”), to serve as President and Chief Executive Officer of Zephyr until terminated. The Johns Agreement provides for an annual base salary of $300,000. Mr. Johns is also eligible to participate in the Omnibus Inventive Plan and to receive equity awards, each as determined by the Board. Mr. Johns also receives medical, dental, prescription and disability insurance coverage, and reimbursement of travel expenses.

In the event that Mr. Johns terminates the Johns Agreement without good reason or the term of the Johns Agreement expires, Mr. Johns would be entitled to his base salary as in effect immediately preceding the termination for a period of 90 days. In the event that he is terminated by us for “Cause,” Mr. Johns would be entitled to his accrued but unpaid base salary and other accrued obligations. “Cause” is defined as occurring upon (i) the conviction of a felony, (ii) willful misconduct or gross negligence, (iii) conduct causing material economic harm to the Company, (iv) a failure to carry out the reasonable and lawful directions of the Board, (v) fraud, embezzlement, theft or dishonesty against the Company, (vi) a violation of a policy or procedure of the Company, or (vii) a breach by Mr. Johns of the Johns Agreement.

Mr. Johns may resign upon giving no less than 90 days’ notice.

Upon a termination of employment, Mr. Johns would continue to be subject to non-solicitation and non-compete restrictive covenants for a period of two years following such termination.

Sharon Binnun’s Employment Agreement

Effective January 1, 2015, Ms. Binnun entered into an employment agreement with the Company (the “Binnun Agreement”), to serve as an executive until terminated. The Binnun Agreement provides for (i) an annual base salary of $300,000 and (ii) an annual cash discretionary incentive of up to $60,000 or greater based on the Board’s approval. Ms. Binnun also receives an automobile allowance and reimbursement of travel expenses.

In the event that Ms. Binnun’s employment is terminated by the Company for any reason within six months after the consolidation, merger, transfer of assets, or other acquisition of the Company, she will receive a lump-sum severance payment equal to six months of her base salary as in effect immediately preceding the termination.

Upon a termination of employment, Ms. Binnun would continue to be subject to (i) a non-solicitation restrictive covenant for a period of two years following such termination and (ii) a non-compete restrictive covenant for a period of one year following such termination.

Estimated Payments Following Termination or Change in Control

We have employment agreements and, in some cases, award agreements for awards granted pursuant to our Omnibus Incentive Plan, with each of our named executive officersMessrs. Garateix, Lusk, Moura and Johns and Ms. Binnun (collectively, the “Agreements”) that entitle them to severance payments on certain types of employment terminations.

For “Cause” Terminations

With respect to equity, in the event of a termination for “cause,” under the Prior Lusk Agreement, Mr. Lusk is required to immediately forfeit unvested shares.shares and under the Prior Garateix Agreement, Mr. Garateix is no longer entitled to any compensation or benefits under the Garateix Agreement. Under these circumstances, each of the other named executive officers’Mr. Moura’s equity awards will be immediately forfeited on the date that: (i) theirhis employment is terminated; (ii) theirhis employment could have been terminated for “cause”; or (iii) there has been a determination that a named executive officerhe engaged in inimical conduct.

In the event that Mr. Johns is terminated by us for “cause,” he would be entitled to his accrued but unpaid base salary and other accrued obligations.

Other Terminations

In the event that Mr. Johns terminates the Johns Agreement without good reason or the term of the Johns Agreement expires, Mr. Johns would be entitled to his base salary and benefits as in effect immediately preceding the termination for a period of 3 months.

“Change of Control” Payments

Under the employment agreementsPrior Garateix Agreement, there were no severance entitlements in connection with Messrs. Lucas and Widdicombe,a termination following a change in control. Under the Garateix Agreement, a “change of control” will generally be deemed to have taken place if: (i) any person, including a “group” as defined in the Securities Exchange Act of 1934, as amended, becomes the beneficial owner of Company securities having greater than 50% of the combined voting power of the then outstanding shares of the Company, subject to certain exceptions, or (ii) the persons who were directors of the Company before such transactions cease to constitute a majority of the Board, or any successor to the Company, as the direct or indirect result of or in connection with, any cash tender or exchange offer, merger or other business combination, sale of assets or contested election, or any combination of the foregoing transactions. Under the Garateix Agreement, in the event that Mr. Garateix is terminated by the Company without cause or if Mr. Garateix terminates his employment for good reason after a change of control, Mr. Garateix shall receive the severance payments for a termination “without cause” or for “good reason,” except that his lump-sum cash severance payment will equal three times his base salary in effect immediately preceding the termination. Under the Lusk Agreement, in the even that Mr. Lusk is terminated by the Company without cause or if Mr. Lusk terminates his employment for good reason after a change of control, Mr. Lusk shall receive the severance payments for a termination “without cause” or for “good reason,” except that his lump-sum cash severance payment will equal 1.5 times his base salary in effect immediately preceding the termination.

Under the Binnun Agreement, in the event that Ms. Binnun’s employment agreements with Messrs. Lucas and Widdicombe, upon the occurrence of a “change of control,”is terminated by the Company for any reason within six months after the consolidation, merger, transfer of assets, or other acquisition of the Company, she will until December 31, 2020, (i) continuereceive a lump-sum severance payment equal to paysix months of her base salary at not less than the level applicable on the change of control date, (ii) pay incentivesas in amounts not less in amount than those paid during the12-month periodeffect immediately preceding the change of control date, and (iii) continue employee benefit programs at levels in effect on the change of control date.termination.

With respect to equity awards, upon a change of control, Mr. Garateix’s and Mr. Lusk’s remaining unvested shares will vest upon the date of the change of control. If Mr. Moura remains employed by the successor entity following a change of control, the dollar value of his unvested awards (as of the change of control date) will be held in escrow and distributed to him in accordance with the vesting schedule in his award agreement. If Mr. Moura’s employment is terminated as a result of the change of control, his unvested awards as of the date of termination will become immediately vested on that date.

With respect to equity awards, upon the death of anyeither of the named executive officers,Mr. Lusk or Mr. Moura, any unvested restricted stock awards will automatically terminate and be forfeited as of the date of death.

“Disability” Payments

Pursuant to Mr. Lusk’s employment agreement,the Prior Lusk Agreement, in the event of hisMr. Lusk’s termination due to “disability,” he will be entitled to all accrued but unpaid base salary and accrued and unused paid time off as of the termination date.

Pursuant to the Garateix Agreement, in the event that Mr. Garateix becomes unable to perform his duties due to illness or injury for a consecutive period of 90 days, then the Company may, within 30 days, suspend his position as an officer of the Company. In the event of such suspension, he shall remain an employee of the Company and receive the compensation and fringe benefits as set forth in the Garateix Agreement through December 31st of the year of his suspension. In the event that Mr. Garateix has not returned to the full-performance of his duties by the end of such suspension period, the Company shall terminate his employment with the Company.

Tax Matters

In the event any payment or benefit to the other executive officers would constitute an excess parachute payment within the meaning of Section 280G of the Internal Revenue Code and be subject to the excise tax imposed by Section 4999 of the Internal Revenue Code, the affected named executive officer will be entitled to the greater of (on a net after-tax basis): (i) the largest amount of the payment that would result in no portion of the payment or benefit being subject to the excise tax under Section 4999 of the Internal Revenue Code or (ii) the entire payment or benefit without any reduction to avoid the excise tax.

Table Showing Estimated Payments Following Termination or Change in Control

The following table shows potential payments to our named executive officers, other than Bruce Lucas and Richard Widdicombe, if their employment terminates under their Agreements. The amounts assume a December 31, 2019,2020, termination date and use the closing price of our common stock as of that date of $13.25$10.13 per share. Please see “Table Showing Payments Upon Separation for Messrs. Lucas and Widdicombe” for information about the severance payments that they received following cessation of their employment in 2020.