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

Filed by the registrant  ☒                            Filed by a party other than the registrant  ☐

Check the appropriate box:

ARGO GROUP INTERNATIONAL HOLDINGS, LTD.

(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):

Argo House

110 Pitts Bay Road

Pembroke HM 08, Bermuda

NOTICE OF THE ANNUAL GENERAL MEETING OF SHAREHOLDERS

The Annual General Meeting (the “Annual General Meeting”) of Argo Group International Holdings, Ltd. (“Argo Group”Group” or the “Company”“Company”), a Bermuda exempted company limited by shares, will be held on May 4, 20186, 2021 at 9:noon local Bermuda time (11:00 am local timea.m. Eastern Time) at 11090 Pitts Bay Road, Pembroke, Bermuda and at such other meeting upon any adjournments or postponements thereof.

The Annual General Meeting is called for the following purposes:

The Board has fixed the close of business on March 7, 201815, 2021 as the record date for determining those shareholders who will be entitled to vote at the Annual General Meeting.

The voteCompany is actively monitoring COVID-19 developments and related guidance issued by public health authorities. If it is determined to be advisable or required, the Company may hold a virtual-only annual general meeting via live webcast. If this step is taken, the Company will announce the decision to do so in advance, and details on how to participate will be posted on the Company’s website and filed with the Securities and Exchange Commission as additional proxy materials.

Whether you plan to be present at the Annual General Meeting or not, you are requested to promptly submit your proxy either electronically via the Internet or by telephone as described on the Notice of each shareholder is important. I urge you to accessInternet Availability of Proxy Materials or proxy card or by completing, signing and returning the proxy materials on the internet orcard to request an electronic or a paper copy of them as promptly as possible. This will ensure that you will be able to complete your proxy card in a timely manner so that your shares will be voted atrepresented. Under our Amended and Restated Bye-Laws, all proxies must be received not less than 48 hours prior to the time of the commencement of the Annual General Meeting.

By Order of the Board of Directors

WHETHER YOU PLAN TO BE PRESENT AT THE ANNUAL GENERAL MEETING OR NOT, YOU ARE REQUESTED TO SUBMIT YOUR PROXY EITHER ELECTRONICALLY VIA THE INTERNET OR BY TELEPHONE AS DESCRIBED ON THE PROXY CARD OR, IF YOU REQUEST A PAPER COPY, BY COMPLETING, SIGNING AND RETURNING THE PROXY CARD TO ENSURE THAT YOUR SHARES WILL BE REPRESENTED.

Craig S. Comeaux

Secretary

March 25, 2021

Important Notice Regarding the Availability of Proxy Materials

For the Annual General Meeting to be Held on May 6, 2021

The Proxy Statement, Notice of Annual General Meeting and 2020 Annual Report to Shareholders are available at https://materials.proxyvote.com/G0464B

TABLE OF CONTENTS

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Argo House

11090 Pitts Bay Road

Pembroke HM 08, Bermuda

PART 1

PROXY STATEMENT

This proxy statement is furnished in connection with the solicitation byon behalf of the Board of Directors (the “Board” or “Board of Directors”) of Argo Group International Holdings, Ltd. (“Argo Group” or the “Company”) of the enclosed proxy to vote common shares of Argo Group’s Group (the “Common Shares (the “Common Shares”” or “shares”) at the Annual General Meeting of shareholders to be held on May 4, 2018,6, 2021, at 9:noon local Bermuda time (11:00 a.m. Eastern Time) at 90 Pitts Bay Road, Pembroke, Bermuda and at such other meeting upon any adjournments, postponements or continuations thereof. This proxy statement and the accompanying proxy card are first being sent or made available to shareholders on March 25, 2021. Note that references to the Company’s website herein do not incorporate by reference the information contained in the website and such information should not be considered a part of this proxy statement.

We are actively monitoring COVID-19 developments and related guidance issued by public health authorities. If it is determined to be advisable or required, we may hold a virtual-only annual general meeting via live webcast. If this step is taken, we will announce the decision to do so in advance, and details on how to participate will be posted on our website and filed with the Securities and Exchange Commission (the “SEC”) as additional proxy materials.

QUESTIONS AND ANSWERS ABOUT THE ANNUAL GENERAL MEETING

Why am I receiving this proxy statement?

The Board of Directors of Argo Group is soliciting your proxy for use at the Company’s 2021 Annual General Meeting to be held on May 6, 2021, at noon local Bermuda time (11:00 a.m. Eastern Time) at 11090 Pitts Bay Road, Pembroke, Bermuda and at such other meeting upon any postponements or adjournments thereof.

As permitted by rules adopted by the United States Securities and Exchange Commission (the “SEC”) and by the provisions Only holders of the Companies Act 1981record of Bermuda, Argo Group is making this proxy statement, the proxy card and the annual report to shareholders (the “proxy materials”) available to shareholders electronically via the Internet. A notice (the “Notice”) that includes instructions on how to access and review the proxy materials and how to submit your proxy online will be mailed to shareholders beginning on or about March 21, 2018. Shareholders may request a printed copy of the proxy materials by following the instructions included in the Notice. In addition, Argo Group will post copies of the 2017 Annual Report on Form10-K and this proxy statement on its web site at www.argolimited.com. The reference to Argo Group’s web site does not incorporate by reference the information contained in the web site and such information should not be considered a part of this proxy statement.

The Annual General Meeting to which the Notice and this proxy statement apply is being convened solely for the purposes discussed in this document. Shares represented by duly executed proxies in the accompanying form received before the Annual General Meeting will be votedshares at the Annual General Meeting. Any shareholder giving a proxy has the power to revoke it at any time before it is voted by (i) filing with the Secretary of Argo Group an instrument revoking the proxy or (ii) submitting another proxy by Internet, phone or mail bearing a later date, duly executed if submitted by mail. Proxies may also be revoked by any shareholder present at the Annual General Meeting who votes in person. If your shares are held in street name, you must contact your broker, nominee or trustee to vote and revoke your proxy. If a shareholder specifies a choice on any matter to be acted upon by means of the ballot provided in the accompanying proxy, the shares will be voted accordingly. If no specification is made, the shares represented by the proxy will be voted in favor of the proposals set forth in the Notice, subject to limitations prohibiting brokers from voting on certain matters on behalf of their clients absent specific instructions (so called “brokernon-votes” as described below in this Proxy Statement).

Argo Group will bear the cost of preparing, assembling and mailing this Proxy Statement and the materials enclosed herewith. In addition, we have retained Georgeson, Inc. to aid in the solicitation of proxies. For these services, we will pay Georgeson, Inc. a fee of $10,500 plus reasonable expenses. Our directors, officers and employees may solicit proxies orally or in writing, without additional compensation. Argo Group will also request that banks, brokerage houses and other custodians, nominees and fiduciaries send proxy materials to the beneficial owners of Argo Group Common Shares and will, if requested, reimburse the record holders for their reasonableout-of-pocket expenses in so doing.

VOTING SECURITIES AND VOTING RIGHTS

Securities Outstanding

The close of business on March 7, 2018 has been fixed as the record date for the determination of shareholders15, 2021 (the “Record Date”) will be entitled to notice of and to vote at the Annual General Meeting or such other meeting upon any adjournments or postponements thereof. On that date,As of the Record Date, there were 29,321,04034,708,284 Common Shares issued, outstanding and entitled to vote. Argo Group has no other voting securities outstanding.

Why did I receive a one-page notice in the mail regarding the Internet availability of proxy materials instead of a full set of proxy materials?

Pursuant to Argo Group’sBye-Laws,rules adopted by the SEC, the Company has elected to provide access to its proxy materials over the Internet. Accordingly, we mailed a majorityNotice of allInternet Availability of Proxy Materials (the “Notice”) to shareholders on March 25, 2021. The Notice contains instructions on how to access the shares entitled to vote, present in person or represented by proxy will constitute a quorummaterials for the transactionAnnual General Meeting, including this proxy statement, the Notice of businessAnnual General Meeting and 2020 Annual Report to Shareholders. The Notice also contains instructions on how to vote. All shareholders will have the ability to access the proxy materials on the website referred to in the Notice or request to receive a printed set of proxy materials by mail. The Company encourages shareholders to take advantage of the availability of the proxy materials on the Internet to help reduce the environmental impact of its annual general meetings.

What proposals are to be presented at the Annual General Meeting.Meeting and what are the Board’s voting recommendations?

EachAs described in further detail later in this proxy statement, the purpose of the Annual General Meeting is to consider and vote upon the following proposals. The Board’s recommendation on each of the proposal is indicated below.

As of the date of the Notice of Annual General Meeting, we knew of no other matters to be presented at the Annual General Meeting.

What is the required vote to approve each proposal?

The election of each director nominee named in this proxy statement and the other proposals will be decided by the affirmative vote of a majority of votes casts.

How will my shares be voted?

Subject to certain restrictions set forth in our Amended and Restated Bye-Laws (the “Bye-Laws”) (as described below), each shareholder of record is entitled to one vote per share held on all matters submitted to a vote of shareholders. Proposals in this proxy statementYour shares will be decidedvoted in accordance with your instructions as follows:

A resolution put toindicated on your proxy. If you are the shareholder of record and sign and return a vote atproxy card without specifying voting instructions, your shares will be voted in accordance with the recommendations of the Board of Directors. All votes will be counted by an inspector of election appointed for the Annual General Meeting, who will be decided on by a show of hands unless a poll has been demanded pursuant to ourBye-Laws. Shares represented at the Annual General Meeting for whichseparately tabulate affirmative and negative votes, are withheld on any matter, shares that are represented by “brokernon-votes” (that is, shares held by brokers or nominees that are represented at the Annual General Meeting but with respect to which theabstentions and broker or nominee has not received voting instructions from the beneficial owner and is not empowered to vote on a particular proposal) and the shares that abstain from voting on any particular matter are not included in the tabulation of the shares voting on such matter, but are counted for quorum purposes. Member brokerage firms of the New York Stock Exchange, Inc. that hold shares in street name for beneficial owners, to the extent that such beneficial owners do not furnish voting instructions with respect to any or all proposals submitted for shareholder action, may vote in their discretion upon the proposal for the ratification of the appointment of Ernst & Young as our independent auditors.non-votes.

Under ourBye-Laws, no “U.S. Person” (as that term is defined in ourBye-Laws) that owns our shares directly, or indirectly through foreign entities, is entitled to exercise voting power on a matter (either directly or through a person whose ownership of shares in us is attributed to such U.S. Person) thatwhere such voting power equals or exceeds 9.5% of the votes conferred on all of our shares entitled to vote on such matter, after taking into consideration all votes held by such U.S. Person directly or through attribution.

How many shares must be present to conduct the Annual General Meeting?

Pursuant to our Bye-Laws, a majority of the outstanding shares carrying the right to vote, present in person or represented by proxy, will constitute a quorum for the transaction of business at the Annual General Meeting. Under Bermuda law, abstentions and “broker non-votes” are counted as present in determining whether the quorum requirement is satisfied. A broker non-vote, as further explained below, occurs when a broker holding shares for a beneficial owner does not vote on a particular proposal because the broker does not have discretionary voting power for that particular item and has not received instructions from the beneficial owner.

What is the difference between holding shares as a “shareholder of record” and as a “beneficial owner”?

If your shares are registered in your name on the Record Date, you are a shareholder of record. When you properly vote in accordance with the instructions provided on the Notice or proxy card, you are instructing the named proxies to vote your shares in the manner you indicate on your proxy.

If your shares are held in the name of your bank, broker or other nominee (herein referred to generally as a “Broker”), which is usually the case if you hold your shares in a brokerage or similar account, your shares are held in “street name.” Your Broker is the shareholder of record for your shares. As the holder of record, only your Broker is authorized to vote or grant a proxy for your shares. If your shares are held in “street name,” you should follow the instructions on your voting instruction form and provide specific instructions to your Broker on how to vote the shares they hold for you.

What is a “Broker Non-Vote”?

A broker non-vote occurs when a Broker submits a proxy on behalf of a beneficial owner for the Annual General Meeting, but does not vote on a particular proposal because such Broker does not have discretionary voting power with respect to that proposal and has not received voting instructions from the beneficial owner. Broker non-votes (like abstentions) will be counted as present for purposes of determining a quorum. Such Broker has the discretion to vote your shares on “routine” matters, but not on non-routine matters. Routine matters include only Proposal 3 (Approval of the appointment of Ernst & Young as our independent auditors for the fiscal year ending December 31, 2021 and to refer the determination of its remuneration to the Audit Committee of our Board of Directors). All other proposals to be presented at the Annual General Meeting are considered “non-routine” and therefore Brokers will not have discretionary authority to vote your shares with respect to the other proposals to be presented at the Annual General Meeting. Therefore, it is important that you instruct your Broker how to vote your shares.

How do I vote my shares?

If you are a shareholder of record with respect to shares on the Record Date. You may vote by one of the following four options:

Even if you plan to attend the Annual General Meeting in person, we encourage you to vote your shares in advance via the Internet, by telephone or by signing, dating and returning your proxy card.

If your shares are held by a Broker in “street name,” please follow the instructions you receive from your Broker to vote your shares. You may need to contact your Broker to determine whether you will be able to vote electronically via the Internet or by telephone. If you wish to vote in person at the Annual General Meeting you must provide an executed proxy from your Broker indicating that you were the beneficial owner of the shares on the Record Date, and that such Broker is giving you its proxy to vote the shares.

Please note that under our Bye-Laws, all proxies must be received 48 hours prior to the time of the commencement of the Annual General Meeting. This means that your proxy must be received by 11:00 a.m. Eastern Standard Time (noon local Bermuda time) on May 4, 2021.

If you return your proxy by mail, please ensure you leave enough time for your proxy to be mailed and received by the inspector of election. Also note that if your shares are held through a Broker, such entity may have even earlier deadlines by which to submit your vote. Please follow their instructions accordingly.

What do I need for admission to attend the Annual General Meeting?

All shareholders attending the Annual General Meeting in person will be required to show valid picture identification. If your Common Shares are in the name of your Broker, you will also need to bring evidence of your share ownership as of the Record Date, such as your most recent brokerage account statement or a copy of your voting instruction form. If you do not have valid picture identification or proof of your stock ownership, you may not be admitted to the meeting. For security purposes, packages and bags will be inspected and you may be required to check these items. Please arrive early enough to allow yourself adequate time to clear security.

Who will count the votes?

All votes will be counted by an independent inspector of election appointed for the Annual General Meeting, who will separately tabulate affirmative and negative votes, abstentions and broker non-votes (if any).

How can I find out the results of the voting at the Annual General Meeting?

We will report voting results of the Annual General Meeting within four business days in a Current Report on Form 8-K or other appropriate filing with the SEC, as applicable.

Can I change my vote?

If your shares are registered in your name, you may revoke your proxy and change your vote prior to the completion of voting at the Annual General Meeting by:

If your shares are held by a Broker “street name” and you wish to revoke a proxy, you should contact your Broker and follow its procedures for changing your voting instructions. You also may vote in person at the

Annual General Meeting to revoke an earlier proxy if you provide an executed proxy from your Broker indicating that you were the beneficial owner of the shares on the Record Date, and that such Broker is giving you its proxy to vote the shares.

Only the latest dated validly executed proxy that you submit will count.

Please note that under our Bye-Laws, all proxies must be received 48 hours prior to the time of the commencement of the Annual General Meeting. This means that your proxy must be received by noon local Bermuda time (11:00 a.m. Eastern Time) on May 4, 2021.

Who will pay the costs of solicitation?

Argo Group will bear the expense of this mail solicitation, which may be supplemented by telephone, facsimile, email and personal solicitation by our officers, employees and agents. To aid in the solicitation of proxies, we have retained Innisfree M&A Incorporated for a fee of $20,000, plus reimbursement of expenses. We may incur additional fees if we request additional services.

Why did I receive multiple copies of the proxy materials?

If you receive more than one package of our proxy materials, it means that you have multiple accounts holding your Common Shares. These may include: accounts with our transfer agent, American Stock Transfer & Trust Company, and accounts with a Broker. In order to vote all of the shares held by you in multiple accounts, you will need to vote the shares held in each account separately. Please follow the voting instructions provided on the Notice, proxy card and any voting instruction card from your Broker that you received to ensure that all of your shares are voted.

What is “householding” and how does it work?

The SEC has adopted rules that permit companies and intermediaries (e.g., brokers) to satisfy the delivery requirements for proxy statements and annual reports with respect to two or more shareholders sharing the same address by delivering a single proxy statement and annual report addressed to those shareholders. This process, which is commonly referred to as “householding,” potentially means extra convenience for shareholders and cost savings for companies.

A single proxy statement will be delivered to multiple shareholders sharing an address unless contrary instructions have been received from the affected shareholders. Once you have received notice from your broker that it will be “householding” communications to your address, “householding” will continue until you are notified otherwise or until you revoke your consent. If, at any time, you no longer wish to participate in “householding” and would prefer to receive a separate proxy statement, please notify your broker and direct your request to Investor Relations, Argo Group, 90 Pitts Bay Road Pembroke, HM 08, Bermuda or by calling 441-296-5858. Shareholders who currently receive multiple copies of the proxy statement at their address and would like to request “householding” of their communications should also contact their broker and the Company.

CORPORATE GOVERNANCE

Director IndependenceOur Strong Corporate Governance Practices

The Board of Directors maintains robust Corporate Governance Guidelines that reflect local and international developments. The Risk & Capital Committee and Audit Committee of the Board of Directors are regularly briefed on emerging governance issues relevant to our international footprint as well as evolving regulatory developments, especially in Bermuda, the U.S., the United Kingdom, and the E.U. Our corporate governance, compliance, risk management, and internal controls policies are reviewed at least annually.

Board Leadership Structure

The Board has chosen to separate the position of Chief Executive Officer from the position of Board Chairman. The Company believes that this separation of positions is an appropriate structure that provides both support and balance for management and overall risk oversight for the Company because it creates a lead director that is independent from management. Separating these positions allows our Chief Executive Officer to focus on developing and implementing the Company’s business plans and supervising the Company’s day-to-day business operations, and allows our Board Chairman to lead the Board in its oversight, advisory, and risk management roles.

Director Independence

The Board has determined that each of its directors and director nominees except Mark E. Watson III,Kevin J. Rehnberg, the President and Chief Executive Officer of Argo Group, is “independent” in accordance with the applicable corporate governance requirements of the listing rules of the NasdaqNew York Stock MarketExchange (“Nasdaq”NYSE”) as currently in effect. In addition, F. Sedgwick Browne, Hector De Leon, Mural R. Josephson, John R. Power, Jr. and Gary V. Woods, who each retired from the Board at the 2020 Annual General Meeting, were considered independent.

Executive Sessions of Independent Directors

In order to promote open discussion among the independent directors, the Board Leadership Structure

schedules regular executive sessions in which those directors meet without management participation. During 2020, the independent directors met in executive session four times. The Chairman of the Board presides over executive sessions. In addition, each Committee of the Board of Directors has chosen to separate the position of Principal Executive Officer (held by the Company’s Chief Executive Officer) from the position of Board Chairman. The Company believes that this separation of positions is an appropriate structure for effectively dealing with bothmeets in executive session without management and risk oversight because it creates a lead director that is independent from management whose role includes, but is not limited to, chairing meetings of the independent directors.participation during regularly scheduled committee meetings.

Code of Business Ethics and Conduct

The Board of Directors has adopted Corporate Governance Guidelines and a Code of Conduct and Business Ethics (the “Code“Code of Conduct”Conduct”) that applies to all its directors, officers and employees, including the principal executive officer and the principal financial officer, copies of which are available on the Company’s web sitewebsite at www.argolimited.com.www.argolimited.comunder the “Investors” tab and then the “Governance” tab. In addition, copies of the Code of Conduct can be obtained, free of charge, upon written request to our principal executive offices as follows: Investor Relations, 11090 Pitts Bay Road, Pembroke HM 08, Bermuda. Any amendments to or waivers of the Code of Conduct that apply to the Company’s Board or its executive officers will be disclosed on our web site. The reference to the Company’s web site does not incorporate by reference the information contained in the web site and such information should not be considered a part of this proxy statement.website.

Committees and Meetings of the Board of Directors

During 2017, theThe standing committees of the Board of Directors wereare the Audit Committee, the Executive Committee, the Human Resources Committee, the Investment Committee, the Nominating and Corporate Governance Committee and the Risk & Capital Committee. The Board of Directors has no other committees. The Board of Directors has adopted written charters for the Audit, Human Resources, Investment, Nominating and Corporate Governance and Risk & Capital Committees that specify the scope of each committee’s responsibilities. Each committee charter is available on our web sitewebsite at www.argolimited.com. The reference towww.argolimited.com under the Company’s web site does not incorporate by reference“Investors” tab and then the information contained in the web site and such information should not be considered a part of this proxy statement.“Governance” tab.

During 2017, the Board of Directors met 4 times, the Audit Committee met 4 times, the Human Resources Committee met 4 times, the Investment Committee met 4 times, the Nominating Committee met 2 times, the Risk & Capital Committee met 4 times and the Executive Committee did not meet. During that time,2020, all directors attended 75% or more of the aggregate meetings of the Board of Directors and of the Committees of the Board on which they servedserved. In addition to regularly scheduled board and committee meetings, the Board holds informational calls with management throughout the exception of Mr. Cash, who was unableyear to attend several meetings duereceive information on matters pertaining to medical issues in the second half of 2017.

Company. While Argo Group does not have a policy requiring directors to attend the Annual General Meeting,Meetings, the Company encourages directors to attend shareholder meetings and all of the directorsdirector nominees attended the Company’s virtual 2020 Annual General Meeting held in JuneApril of 2017.2020.

Executive Sessions of Independent Directors

In order to promote open discussion among the independent directors, the Board of Directors schedules regular executive sessions at least 2 times each year in which those directors meet without management participation. During 2017, the independent directors met in executive session 4 times.

Board Committees

Executive Committee

The Executive Committee consists of Messrs. Woods, De Leon, and Watson. The Executive Committee may exercise all powers and authority of the Board of Directors in the oversight of the business of the Company.

Audit Committee

TheEach member of the Audit Committee consists of Messrs. Browne, De Leon, Josephson and Power, each of whom is “independent” and meets the other requirements for audit committee membership as defined by applicable NasdaqNYSE listing rules and SEC rules for audit committee members.

Messrs. Bradley and Donner are qualified as “audit committee financial experts” within the meaning of applicable SEC rules and regulations governing the composition of the Audit Committee.

The Audit Committee assists the Board in its oversight of (i) the quality and integrity of the accounting, auditing,Company’s financial statements, (ii) the Company’s compliance with legal and financial reporting processesregulatory requirements, (iii) the qualifications and independence of the Company.independent registered public accounting firm, and (iv) the performance of the Company’s internal auditing department and the independent registered public accounting firm. Its primary responsibilities, among other items, include (a) review ofreviewing and discussing with management and the outside audit firm the quarterly and annual financial results and other financial information of the Company, (b) the appointment, replacement, compensation and oversight of independent auditors, (c) review ofreviewing all recommendations by the auditors with respect to accounting methods and internal controls of the Company, (d) the review and advance approval of audit andnon-audit services provided by the auditors, the scope of such audits and services and the impact on the auditors’ independence, (e) oversight of the effectiveness of the Company’s internal audit function, and (f) otherwise providing oversight for the accounting and financial reporting processes of the Company and the audits of the financial statements of the Company. The Committee’s role also includes discussing with Senior Management, Internal Audit and the independent auditorsCompany, (g) providing oversight of the Company’s processes for managing its business and financial risks and processes for compliance with significant applicable legal and regulatory requirements, in relation toand (h) the Company’s accounting and financial reporting processes.review, approval or ratification of all related party transactions. In addition, the Committee establishes procedures for complaints relating to accounting, internal accounting controls or auditing matters as well as procedures for confidential, anonymous submission by Company employees of any concerns regarding questionable accounting or auditing matters.

In recommending an independent auditorsregistered public accounting firm for the Company, the Audit Committee annually considers the performance and integrity of the independent auditors, the experience and qualifications of the lead audit partner, the geographic scope of their practice as compared to the Company’s geographic scope, their insurance industry expertise, the appropriateness of their fees, the Public Company Accounting Oversight Board (“PCAOB”) reports on the firm and its peers, and other factors deemed appropriate.

In connection with performing its oversight role related to the audited consolidated financial statements contained in the Company’s Annual Report on Form10-K, the Audit Committee has:

Based on these reviews and discussions, the Audit Committee recommended to the Board of Directors that the Company’s audited consolidated financial statements be included in the Company’s Annual Report onForm 10-K for the year ended December 31, 2017, for filing with the Securities and Exchange Commission.

AUDIT COMMITTEE:

Mural R. Josephson, Chairman

F. Sedgwick Browne

Hector De Leon

John R. Power, Jr.

Audit Committee Financial Experts

Mural R. Josephson is qualified as an “audit committee financial expert” within the meaning of applicable SEC rules and regulations governing the composition of the Audit Committee. In addition, the Audit Committee has determined that he has the appropriate experience and background to satisfy the “financial sophistication” requirements of Nasdaq’s listing rules.

Investment Committee

The Investment Committee consists of Messrs. Cash, Ramji, Tonelli, Watson and Woods. The Investment Committee assists the Board in the oversight of the Company’s key investment objectives, strategies and policies. In addition, the Investment Committee oversees the Company’s M&A activities. The Committee’s responsibilities include, among other items, (a) approval of the Company’s Investment Policy including the investment policies, strategies,guidelines and asset allocation ranges set forth therein, (b) oversight of the Company’s investment transactions (b) review ofand its outside investment managers to determine whether such investment transactions are in accordance with the Company’s Investment Policy, (c) ensuring that appropriate selection criteria are developed to identify and select the Company’s outside investment managers and periodically reviewing the performance of the Company’s investment portfolios and investment managers, (c) review of the criteria used to select outside investment managers, (d) oversight of management’s administration of the Company’s investment portfolio, including recommended strategic asset allocations and approvalthe performance of allocations to outside investment managersthe portfolio under anticipated and (d)stress test scenarios, and (e) approval of any Company derivative policy and review of management analysis and reports on potential hedging programs and derivative transactions. All investment transactions are ratified by the full Board of Directors.

Human Resources Committee

TheEach member of the Human Resources Committee consists of Messrs. Cash, De Leon, Power and Woods, each of whom is “independent” in accordance with the applicable corporate governance requirements of the listing rules of NasdaqNYSE as currently in effect. Each member of the Human Resources Committee also qualifies as a“non-employee director” under Section 16 of the Exchange Act and as an “outside director” under Section 162(m) of the U.S. Internal Revenue Code.Act. The Human Resources Committee’s responsibilities include, among other items, (a) overseeing the compensation of the Company’s executive officers and directors, (b) reviewing and discussing with the Company’s management the Compensation Discussion and Analysis contained in this proxy statement, (c) producing an annual report on executive compensation for inclusion in the Company’s proxy statement, (d) overseeing and advising the Board of Directors on the adoption of plans and policies that govern the Company’s compensation programs, (e) reviewing management’s succession plans for the Company’s Chief Executive Officer and other primary executive officers, and (f) determining and monitoring stock ownership guidelines.

Human Resources Committee Interlocks and Insider Participation

None of the members of the Human Resources Committee during the fiscal year 2017 or as of the date of this proxy statement is or has been an officer or employee of the Company. See “Related Persons Transactions – Certain Related Person Transactions” below for certain transactions involving the Company in which Mr. Woods may be deemed to have an indirect interest. The Company does not deem such interest to be material. No interlocking relationships existed between any member of the Board of Directors or Human Resources Committee and any member of the board of directors or compensation committee of any other company during the last fiscal year.

Risk & Capital Committee and Oversight

The Risk & Capital Committee consists of Mr. Browne, Ms. Lehane, Ms. Nealon, Mr. Tonelli and Mr. Watson. While the Board of Directors has the ultimate responsibility for overseeing and approving the Company’s risk strategy, risk appetite and risk tolerance levels, the Risk & Capital Committee provides oversight of the Company’s policies and procedures relating to compliance and risk management and also oversees the adequacy of the Company’s capital as measured using our own economic capital model and against various regulatory and other requirements taking into account all risks to which the Company is exposed. Risk management is a collaborative effort of management, the Company’s Board of Directors and several functions within the Company that are focused on risk. Please see the section entitled “Enterprise Risk Management and Governance Frameworks” below for further details.

The Company’s enterprise risk management framework consists of three lines of defenseNominating and begins at the departmental level. Each business and function are charged with the task of identifying, assessing, measuring, monitoring, reporting and mitigating risks associated with their respective responsibilities. The Company’s Chief Risk Officer, who gives presentations on risk management matters directly to the Risk & Capital Committee, leads the second line of defense and plays a key role in risk management by coordinating, facilitating and overseeing the effectiveness and integrity of our risk management activities. This risk management function is also charged with establishing, maintaining and enhancing the methodology and tools used to identify and evaluate risks and, where risks are outside our risk appetite, ensuring that there is an appropriate response applied by the respective risk owner. The Internal Audit department provides a third line of defense by assessing the effectiveness of our risk management processes, practices and internal controls and providing timely feedback and assurance to the Audit Committee on the adherence to our risk management framework. The Head of Internal Audit reports on issues related to the internal control framework directly to the Audit Committee.

The Company believes that the foregoing enterprise risk management framework and oversight activities are structured in a way that enables us to take an active approach to risk management in a dynamic legal, regulatory and business environment. Through the efforts of management, our internal risk management function and the Board of Directors, we seek to manage our risk exposures within agreed risk tolerances, while recognizing that taking appropriate risks enables us to exploit opportunities beneficial to the Company and its shareholders.

NominatingCorporate Governance Committee

TheEach member of the Nominating Committee consists of Messrs. Browne, Power, Tonelli and Woods, each of whomCorporate Governance Committee is “independent” in accordance with the applicable director independence rules of NasdaqNYSE as currently in effect. The purpose of the Nominating and Corporate Governance Committee is to (a) establish criteria for Board member selection and retention, (b) identify individuals qualified to become Board members, (c) review and recommend to the Board individuals to be nominated orre-nominated for election as directors, including nominees submitted by shareholders in accordance with the requirements of ourBye-Laws as well as the Shareholder Recommendation Procedure set forth in our Nominating and Corporate Governance Committee charter, or to fill vacancies on the Board, and (d) recommend directors for appointments to one or more of the Board’s standing committees. The Committee is also charged with establishing evaluation criteria and an evaluation process applied by the Board and each Committee in its self-evaluation process.

Board Refreshment and Cooperation Agreement

The diverse skillset of our Board is enhanced by both the fresh perspectives brought by our newer directors, as well as the industry and Company-specific expertise of our longer-tenured directors, who have the experience of guiding our Company through the extended business cycles faced by the insurance industry. The Board experienced significant refreshment events in late 2019 and in 2020, both as a result of the Board’s internal refreshment efforts and as a result of the Cooperation Agreement by and among the Company and Voce Catalyst Partners LP, Voce Capital Management LLC, Voce Capital LLC and Voce Catalyst Partners New York LLC (collectively, “Voce”), dated as of December 31, 2019. Following the 2020 Annual General Meeting, five of our longer-tenured directors retired from the Board — Messrs. Woods, Browne, De Leon, Josephson and Power. The Board appointed Ms. McFate as director on February 7, 2020, and shareholders elected Messrs. Bailey, Donner and Rehnberg to the Board at the 2020 Annual General Meeting.

Director Qualifications and DiversityProcess for Nominating Directors

The Nominating and Corporate Governance Committee may receive recommendations for director nominees from various sources such as officers, directors and shareholders and it may also use third party consultants such as search firms to assist in identifying and evaluating potential nominees. The Nominating and

Corporate Governance Committee assesses several factors when evaluating director nominees including, but not limited to, the current needs of the Board and, with regard to a nominee, their: (a) integrity, honesty and accountability; (b) successful leadership experience and strong business acumen; (c) forward-looking strategic focus; (d) collegiality; (e) gender and ethnicity, (f) independence and absence of conflicts of interests; and (f)(g) ability to devote necessary time to meet director responsibilities. In addition, the Nominating and Corporate Governance Committee looks for nominees exhibiting specific skills and expertise in the following areas: (a) accounting and finance; (b) business operations; (c) business strategy; (d) corporate governance; (e) technology/digital strategies; (f) executive leadership; (g) industry knowledge; (h) international operations/global markets; (i) investment management; (j) legal/regulatory; and (k) risk management. The Nominating and Corporate Governance Committee will ultimately recommend nominees that it considers to be fit and proper who will enhance the Board’s ability to oversee, in an effective manner, the management of the affairs and business of the Company. While the

The Nominating Committee does not have a formal policy when considering the overall composition of the Board with regard to the consideration of diversity

in identifying director nominees, the Nominatingand Corporate Governance Committee seeks a diverse and appropriate balance of members who have the experience, qualifications, attributes and skills that are necessary to oversee a publicly traded, growth oriented international insurance organization that operates in multiple jurisdictions. In addition, the Nominating and Corporate Governance Committee seeks directors with experience in a variety of professional disciplines and business ventures that can provide diverse perspectives on the Company’s operations. The Committee evaluates the types of backgrounds that are needed to strengthen and balance the Board based on the foregoing factors and will nominate candidates to fill vacancies accordingly. For a discussion of the specific experiences, qualifications, attributes or skills that led the Nominating and Corporate Governance Committee to conclude that each director should serve on the Company’s Board, of Directors, see the skills chart and biographical information section beginning on page 12.21.

Process for Nominating Directors

The Nominating Committee may receive recommendations for director nominees from various sources such as officers, directors and shareholders and it may also use third party consultants to assist in identifying and evaluating potential nominees. The Nominating Committee did engage a third-party search firm to procure the appointments of Ms. Lehane and Mr. Ramji. The Nominating Committee will consider and evaluate a director candidate recommended by a shareholder in the same manner as a candidate recommended by an officer, director or consultant.

Shareholders wishing to recommend a director candidate to serve on the Board may do so by providing advancea written noticerecommendation to the Company. To make a director nomination at the 2019 Annual General Meeting, a shareholder must follow the same procedures required for submitting a shareholder proposal. See “Shareholder Proposals for 2019 Annual General Meeting” beginning on page 46 for a description of these procedures. NoticesAny recommendations should be sent to Argo Group International Holdings, Ltd. c/o Craig S. Comeaux, Secretary, 11090 Pitts Bay Road, Pembroke HM 08, Bermuda. Any such notice must also meet certainThe Company will apply the same standards in considering director candidates recommended by shareholders as it applies to other requirements specifiedcandidates. Once the Nominating and Corporate Governance Committee receives a recommendation from a shareholder, it may request additional information from the candidate about the candidate’s independence, qualifications and other information that would assist the Nominating and Corporate Governance Committee in ourBye-Lawsevaluating the candidate, as well as certain information that must be disclosed about the Shareholder Recommendation Procedure set forthcandidate in our Nominating Committee charter.the Company’s proxy statement, if nominated. Shareholders may also directly nominate a candidate for director pursuant to the advance notice provisions of the Company’s Bye-Laws.

Shareholder Communication with Board MembersEnterprise Risk Management and Governance Frameworks

Overview

The Company hasbelieves that its enterprise risk management framework and oversight activities are structured in a way that enables us to take an active approach to risk management in a dynamic legal, regulatory and business environment. Through the efforts of management, our internal risk management function and the Board, we seek to manage our risk exposures within agreed risk tolerances, while recognizing that taking appropriate risks provides us with opportunities that are beneficial to the Company and its shareholders.

Risk Management Policy

Conducting our insurance business operations and related services in a prudent manner requires us to establish sound governance mechanisms, including a sound risk management and internal controls framework. The Company is committed to establishing and maintaining a sustainable risk management framework as an integral part of its business model supporting business planning and capital management.

Enterprise Risk Management (“ERM”) is a company-wide process with oversight from the Board that identifies, assesses, monitors, manages and reports risks that could materially influence our ability to deliver on our strategic objectives.

We consider the implementation of our ERM framework as a strategic imperative to enhance shareholder value, not only to meet legal and regulatory requirements but also to gain a competitive edge by improving its understanding of our risks and capital requirements for solvency on a per risk and an aggregated basis. we have designed our framework for managing enterprise risks to be aligned with international standards, such as ISO 31000, and to take into consideration the interests of our shareholders, policyholders and other counterparties.

The objectives of our ERM Framework are designed to ensure that:

Risk Management Strategy

Our risk management strategy encompasses our Three Lines of Defense Model and Risk Appetite Framework, as further explained below, as methods for addressing and managing material business risks. Our strategy is based on and implemented through the respective policies, targets, guidelines, requirements and budgets approved by the Risk & Capital Committee of the Board on a periodic basis. Our strategy is reviewed annually and ERM objectives are agreed upon by the Risk & Capital Committee each year.

The ERM framework continues to be developed and enhanced over time in response to market developments and tested against external Risk Maturity Model standards. The Chief Risk & Sustainability Officer (the “CR&SO”) annually presents to the Risk & Capital Committee a review of the effectiveness of risk management across the organization. Additionally, in 2020, the Risk & Capital Committee commissioned an independent assessment of the effectiveness of our ERM framework.

Three Lines of Defense Model

The organizational boundaries of our internal control framework consist of three lines of defense:

Risk Management Framework

The focus of our risk management framework is on “reasonably foreseeable material risks,” meaning those exposures (financial and non-financial, on and off-balance sheet, current and contingent exposures) that we can identify in advance as having the potential, should they occur, to change the way relevant stakeholders would assess our solvency and/or liquidity position or risk profile. Relevant stakeholders include the Board, senior management, policyholders, investors and the various types of entities that monitor and regulate our business activities and securities.

Key elements of our risk-management framework are summarized below:

Risk Appetite Framework

The Risk Appetite Framework brings together the overall approach for articulating and managing risk appetite, risk preferences, risk tolerances, and risk limits. It describes how this is organized and what processes and procedures underpin its implementation in practice. Our framework is intended to provide clarity regarding acceptable amounts of risk to assist our decision makers in the Company.

Our Risk Appetite Framework achieves this by defining our ability to take risk through a series of qualitative risk appetite statements that are communicated across the organization, supported by quantitative risk appetite measures and risk tolerances and limits. The risk appetite is based on our available capital and liquidity and is reflected in Board-approved business plans. The CR&SO advises the Board on periodic changes to risk appetite and risk tolerances, which are formally approved annually. Risk tolerances define acceptable boundaries in terms of volatility and provide a frame of reference to align behaviors in the Company.

Our Risk Appetite Framework is reflected in our strategic and business planning. We actively use our internal capital model to track risk tolerance limits and allocate capital to the businesses with the greatest potential to exceed ROAC targets, while staying within agreed risk limits. In the event of risk tolerances being exceeded, internal guidelines ensure appropriate escalation and management actions. If necessary, risks are ceded or hedged through reinsurance, derivatives, or other forms of risk transfer in accordance with our policies.

Risk tolerances and limits encompassed in our Risk Appetite Framework include:

All significant policies and procedures associated with our Risk Appetite Framework are documented in writing and available to the Board, management and employees.

Risk Aware Culture

By embedding risk management into our decision-making and creating risk champions at the senior management level, it allows us to oversee risks from a likelihood and consequential perspective and to prioritize the risks most important for senior management and Board oversight. Regular environmental scanning is a key to avoiding or mitigating risks before they become critical.

Information Security and Data Protection

Our information security program and approach are based on the National Institute of Standards and Technology Cybersecurity Framework. In 2020 a third-party auditor performed an independent assessment of our

information security and data protection program. With the findings, we take a quantitative, risk-based approach in developing our strategic roadmap. The latest results indicate that the maturity of the current program is above the insurance industry average. However, as part of continuous improvement, we strive to continue to mature and build a robust and resilient environment to protect and defend against bad actors.

The Company maintains a Data Protection Framework and program that includes an Information Security Policy, Privacy Policy, and Third-Party Risk Management Program, with a commitment to carefully managing personal information we require to operate our business and comply with all regulations in the jurisdictions in which we operate, including specifically addressing the rights of individuals regarding control of data we may hold related to them. Policies are derived from internationally recognized privacy and cybersecurity regulations, frameworks, and principles. During 2020 we experienced no material data privacy breaches involving personal information or customer information.

We only share personal information with affiliates, business partners, third-party service providers, or vendors when we have a legitimate business purpose for doing so and when permissible by law. We require third parties to maintain similar standards to ours to protect personal information as verified by our due diligence process. We have implemented a holistic and consistent risk mitigation process to identify and assess the cyber posture of third parties providing commodities or services to any of Argo’s legal entities.

We have implemented multiple layers of data protection to minimize the risks to systems, personal information, and the privacy of individuals. Such protection includes perimeter security controls, network security controls, endpoint security controls, application security controls, data security controls, logical and physical access controls, maintaining up-to-date inventories (authorized hardware and software), system hardening and monitoring, usage of modern protection software and third-party risk assessments, 24/7 monitoring and response, testing of incident response procedures (table-top exercises), annual information security awareness training, and monthly phishing tests of all Argo employees. During 2020 we experienced no material cybersecurity or data privacy breaches. The Chief Security Officer reports to the Board Risk & Capital Committee at least twice per year on these matters.

Shareholder Engagement

Our Board believes that shareholder engagement is essential to understanding our investors’ interests and is a key part of our commitment to strong corporate governance. For more information regarding our recent engagement efforts and our response, please refer to the section entitled “Compensation Discussion and Analysis — Shareholder Engagement and Responsiveness to 2020 Advisory Vote on Executive Compensation” on page 36.

In addition to this recent shareholder engagement effort, the Company regularly meets with its investors throughout the year. These meetings are conducted at major financial services industry conferences and at events sponsored by the Company and are attended by various members of our senior management. Our independent directors also periodically engage with our shareholders, in an effort to pursue important dialogue. All of these engagements cover a variety of matters that are important to our shareholders, including recent developments at the Company, our financial and operational performance, our long-term strategic and financial goals and industry-wide trends, and other topics that may be raised by our shareholders. The Company also welcomes opportunities to meet with its significant shareholders to discuss and receive feedback on matters related to the Company’s corporate governance and related environmental and social issues.

Our Board receives regular briefings on these shareholder meetings and incorporates the resulting input as appropriate.

Shareholders and other interested parties who wish to communicate with the Board, of Directors, a specific director or the independent directors as a group. Shareholdersgroup may send written communications to Argo Group International Holdings, Ltd. c/o Craig S. Comeaux, Secretary, 11090 Pitts Bay Road, Pembroke HM 08, Bermuda. The Secretary

will review the communication and forward such communication to the individual director or directors to whom the communication is directed, if any. If the communication does not specify a recipient, the Secretary will forward it to the full Board of Directors or to the directors the Secretary believes are most appropriate.

Corporate Responsibility

We recognize that our stakeholders are increasingly focused on our approach to corporate responsibility, including environmental and social matters. In response, Argo Group has taken a structured approach to ensure sustainability matters are incorporated into its business operations. The Company has also enhanced its focus on environmental, social and governance (“ESG”) disclosure on the Company website. For our latest ESG report, refer to our website, www.argolimited.com under the heading “Investors.”

Argo Group established a Sustainability Working Group (“SWG”) in 2016, which is dedicated to the oversight of sustainability and ESG policies, processes and issues facing the organization. The SWG coordinates Argo Group’s approach and maintains a sustainability threat and opportunity assessment. This risk assessment considers both upside (opportunity) and downside (threats) risks that could impact Argo Group as related to sustainability matters. The SWG receives a detailed threat and opportunity analysis of the major sustainability risks facing the organization every six months and escalates key issues to the ERM steering committee. The CR&SO reports on material sustainability-related issues, including topics related to climate change, to the Board’s Risk & Capital Committee on a quarterly basis as required.

Environment

We demonstrate our commitment to addressing climate change issues through our active membership in ClimateWise, a global insurance industry leadership group facilitated by the University of Cambridge Institute for Sustainability Leadership. As part of our membership, we have provided disclosures in line with the ClimateWise Principles, which guide members’ contribution to the transition to a low-carbon, climate-resilient economy – these being aligned to the Task Force on Climate-related Financial Disclosure (TCFD) recommendations – and we continue to work toward achieving these goals as applicable to the Company. During 2020, we also disclosed the Company’s greenhouse gas emissions for scope 1, 2, and 3 inventories against ISO 14064-1 and have set targets for their reduction for 2021, based on a 2019 baseline year. For more information, refer to our website, www.argolimited.com under the heading “About” and then “Corporate Responsibility.”

Focus on Climate Change Risk: We have classified climate change as a material emerging risk, and it is regularly monitored for the primary purpose of assessing the potential impact of climate change on Argo Group’s business operations, insurance products, and clients. We continue to monitor and evaluate scientific and political developments through our emerging risk process and exposure management activities.

Argo maintains its own view of natural catastrophe risk informed by proprietary models, which is used to make underwriting and management decisions. It is based on a combination of third-party vendor models, plus our in-house adjustments specifically recognizing factors such as climate volatility. In cases where a model does not exist or is not appropriate, we have developed proprietary models (e.g., for North American Wildfires). We have considered the effect of climate change on historical U.S. hurricane landfall rates by region and category. However, we recognize that considerable uncertainty remains. We are unable to explicitly isolate the effect of climate change to quantify its effect on losses. We regularly consider potential climate change scenarios within our Stress & Scenario Testing Framework and in completing validation of our catastrophe and capital models. We are piloting the development of more detailed climate tests in line with Prudential Regulatory Authority (PRA) expectations under their Policy Statement PS11/19. The scenario analysis is based on both a short-term view of financial risks within the current business planning horizon and also a long-term view taking into consideration scenarios where average global temperatures continue to rise consistent with a 2-degree Celsius overall rise and/or scenarios where a transition to a low-carbon economy occurs in either an orderly or disorderly manner over the next 15 to 20 years.

Social

Diversity and Inclusion: We are committed to fostering and preserving an inclusive and diverse culture. The collective sum of the individual differences, life experiences, knowledge, education, innovation, self-expression, unique capabilities and talent that our employees invest in their work represents a significant part of not only our culture but our reputation and the Company’s achievements. To this end, Argo adopted and published a Board-approved Diversity & Inclusion (“D&I”) policy in October of 2019, coupled with a new D&I program to be seen overseen by a Diversity & Inclusion Committee. During 2020, Argo established this D&I Committee and a formal D&I Vision Statement. We also established nine active employee resource groups and conducted the annual Companywide Employee Engagement survey designed to provide management with actionable insights into employee wellbeing and sense of inclusion.

Training and Development: We believe developing our employees professionally and personally strengthens our entire organization. Our strategy incorporates a strong focus on talent management, carefully planning our workforce needs and matching these needs through thoughtful, cadenced talent retention, development, promotion and acquisition plans. We provide innovative digital and experiential tools and opportunities to assist our team members with career development and in building connections with peers and mentors, which we believe naturally supports positive business performance. We are intensely committed to developing our global team, and we operate through structured annual talent management and succession planning processes to support business continuity.

Philanthropy: Argo Group is dedicated to improving the communities in which we live and work. Argo’s philanthropic contributions are guided by the same entrepreneurial spirit and targeted, specialized focus that thrives among our workforce. We give back in a variety of ways – through volunteering; corporate contributions; local, employee-led community relations committees; and a generous matching-gifts program. The vast majority of Argo’s contributions are guided by our employees in our local communities around the world.

The Company’s Corporate Contributions Policy applies to all of the above programs and sets forth a governance and oversight framework, overseen by Argo Group’s communications team and the Human Resources Committee of the Board of Directors. The policy is reviewed on an annual basis, and any recommended revisions are provided to the Human Resources Committee for approval. Additionally, Argo Group’s communications team provides quarterly reports to the Human Resources Committee of the Board of Directors, summarizing budget updates and contributions made for all of the Company’s contributions programs.

Responsible Investment: During 2019, we established a Responsible Investment Policy and made a public commitment by signing up to the United Nations Principles of Responsible Investment. We continue to hold some investments in the energy sector, representing less than 5.0% of our total investment portfolio. Fluctuations in oil prices have disrupted the market values for this sector, particularly for oil exploration, production and servicing companies. We have reduced our exposures to the mining sector and anticipate these being run-off over time. We have undertaken stress- and scenario-testing exercises to understand the implications of stranded asset exposure on our portfolio. We understand investors’ increasing influence through measures such as ESG indices, and we continue to closely monitor and evaluate these developing trends.

Vendor Management: Our vendor management policy, ERM framework and other associated policies and practices comply with the requirements of the regulatory jurisdictions in which we operate and require that our due diligence and on-boarding procedures consider a range of risk factors prior to a vendor’s appointment. These considerations include, but are not limited to, each vendor’s financial stability; anti-money laundering, bribery and corruption compliance; economic sanctions compliance; business continuity arrangements; and assessment of the vendor’s operation against international best-practice standards for health and safety, environmental management, labor relations, human rights performance, and governance and accountability.

Other Policies: Argo Group maintains policies promoting human rights; occupational health and safety management; and environmental management in our operations. For more information, refer to our website, www.argolimited.com under the heading “About” and then “Corporate Responsibility.”

Related PersonsPerson Transactions

Policy for Evaluating Related Person Transactions

The Board of Directors has adopted a written policy relating to the Audit Committee’s review and approval of transactions with related persons that are required to be disclosed in proxy statements by SEC regulations (“related person transactions”transactions”). A “related person”“related person” is defined under the applicable SEC regulation and includes our directors, executive officers and 5% or more beneficial owners of our Common Shares. Management administers procedures adopted by the Board of Directors with respect to related person transactions and the Audit Committee reviews and approves all such transactions (including the one described below). At times, it may be advisable to initiate a transaction before the Audit Committee has evaluated it, or a transaction may begin before discovery of a related person’s participation. In such instances, management consults with the Chairman of the Audit Committee to determine the appropriate course of action. Approval of a related person transaction requires the vote of the majority of disinterested directors on the Audit Committee and the Audit Committee

must determine that the transaction is fair and reasonable to the Company for a related person transaction to be approved. The Audit Committee periodically reports on its consideration of related party activities to the Board of Directors.Board. The written policy relating to the Audit Committee’s review and approval of related person transactions is available on our web sitewebsite at www.argolimited.com.www.argolimited.com. The reference to the Company’s web sitewebsite does not incorporate by reference the information contained in the web sitewebsite and such information should not be considered a part of this proxy statement.

Certain Related Person Transactions

Kinetica Partners, LLC. In 2013, our Surety unit received a submission through its established broker network to issue approximately $13 million of surety bonds on behalf of Kinetica Partners, LLC (“Kinetica”Kinetica”) in connection with a Gulf of Mexico pipeline project. Mr. Gary Woods, the former Chairman of our Board of Directors,who served in such role until the 2020 Annual General Meeting, is also the Chairman of the Boardboard of Directorsdirectors of Kinetica, and beneficially owns 10% of Kinetica through a family trust. The submission was underwritten, priced and bound in the ordinary course of business by the Surety unit. The terms and conditions of the surety bonds that were issued and the premium charged to Kinetica for issuance of the bonds, were consistent with those routinely applied and charged for similarly situated risks bound for unrelated third-parties. As of December 31, 2017,2020, approximately $12 million of the surety bonds were still outstanding. Per the Surety unit’s standard requirements in connection with the issuance of surety bonds, Kinetica and Mr. Woods, in his personal capacity, among others, executed our Surety unit’s standard form of indemnity agreement holding our Surety unit harmless against any and all losses and expenses incurred resulting from the issuance of the surety bonds.

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERSHIPOWNERS AND MANAGEMENT

Security Ownership of Principal Stockholders and Management

The following table sets forth certain information regarding the beneficial ownership of our Common Shares as of March 7, 2018the Record Date of each person known to Argo Group to beneficially own more than 5% of the Common Shares. TheUnless otherwise noted in the footnotes following the table, the information for each of these beneficial owners is based solely on information as of December 31, 20172020 reported on a Schedule 13G or Schedule 13D, as applicable, filed by such owner with the Securities and Exchange Commission.SEC.

The following table sets forth certain information regarding the beneficial ownership of the Common Shares as of March 7, 2018the Record Date, unless otherwise indicated, of (i) each director or director nominee of Argo Group, (ii) each individual who has been identified as a named executive officer (“Named Executive Officer”Officer” or “NEO”“NEO”) of Argo Group or its subsidiaries, and (iii) all directors and individuals who have been identified as executive officers of Argo Group as a group:

PROPOSAL 1

1: ELECTION OF DIRECTORS

Board of Director Nominees

The election of directors will be decided by an equal number of directors inordinary resolution as to each class. If this results innominee; that is a fraction of 1/3, one additional director will be placed into Class III. If this results in a fraction of 2/3 one director will be placed into Class II and one into Class III. The Company’sBye-Laws further provide that the Board mayre-designate directors to different classes so that they conform to the preceding formula. We believe a classified board structure is in the best interests of our shareholders because stability in Board membership provides continuity in the guidance management receives from the Company’s Board of Directors with respect to the Company’s long-term strategy.

Four Class II directors are to be elected at the 2018 Annual General Meeting. The Nominating Committee has nominated Hector De Leon, Mural R. Josephson, Dymphna A. Lehane and Gary V. Woods, each of whom is presently serving on the Board, to stand forre-election as Class II directors. Each of them was recommended forre-election by the Nominating Committee for considerationresolution duly adopted by the Board of Directors, which has already occurred, and proposal to our shareholders. If elected, the four nominees will serve as Class II directors for three-year terms until the Annual General Meetingthen approved by

shareholders with a simple majority of shareholdersvotes cast in 2021person or until their successors have been elected and qualified. It is intended that proxies willby proxy. Votes may be votedcast in favor of these persons. If, foror against each nominee, or a shareholder may abstain from voting. Abstentions and broker non-votes, if any, reason, anywill not count as votes cast and, therefore, will have no effect on the outcome of the nominees is not able or willing to serve as a director when the election occurs (a situation which is not presently contemplated), it is intended that the proxies will be voted for the election of a substitute nominee in accordance with the judgment of the proxy holder.directors.

THE BOARD OF DIRECTORS RECOMMENDS THAT SHAREHOLDERS VOTE FOR THE ELECTION OF THE NOMINEES LISTED ABOVE AS DIRECTORS AND, UNLESS DIRECTED OTHERWISE, IT IS THE INTENTIONEACH OF THE PROXIES NAMED IN THE FORM OF PROXY THAT ACCOMPANIES THIS PROXY STATEMENT TO VOTE FOR SUCH NOMINEES AS DIRECTORS.

For Messrs. Cash, De Leon, Power, Watson and Woods, the duration of service as a director stated below includes service on the board of directors of Argonaut Group, Inc. prior to its 2007 merger with the Company.

Biographical Information for the Class II Nominees to be Elected this YearBoard Leadership Skills

Hector De Leon (71) became a director in 2003. Mr. De Leon is the chairman of the board of directors of De Leon & Washburn, P.C., a law firm based in Austin, Texas, which he founded in 1977. Prior to 1977, Mr. De Leon was the General Counsel of the Texas State Insurance Board. From February 1985 to November 1997, Mr. De Leon served as a director of Titan Holdings, Inc., a publicly traded property and casualty insurance holding company. Mr. De Leon brings to the Board experience and skills relating to the insurance regulatory environment in which the Company operates combined with a corporate legal background. In addition, Mr. De Leon’s experience includes prior service as a director of a publicly traded, growth oriented, specialty property and casualty insurance holding company.

Mural R. Josephson (69) became a director in 2004. Mr. Josephson is a Registered Certified Public Accountant in Illinois. Mr. Josephson retired from Kemper Insurance Companies (“Kemper”) in 2002. During his5-year tenure at Kemper, he held key management positions, including senior vice president and chief financial officer and senior vice president of finance. Prior to joining Kemper, Mr. Josephson held several senior level positions at KPMG, including 19 years as an audit partner. While at KPMG, he was a member of the National Insurance Practice Committee and a member of the Professional Practice Review Committee. Mr. Josephson has been a director of HealthMarkets, Inc., an insurance holding company, since May of 2003 and is currently

chairman of its Audit Committee. He was also a director of SeaBright Holdings, Inc., an insurance holding company traded on the NYSE until February 2013, and its wholly owned subsidiary, SeaBright Insurance Company, from July 2004 until February 2013 and was serving as the chairman of its Audit Committee. In addition to his historical knowledge of the Company’s operations and his extensive background in the insurance sector, Mr. Josephson brings to the Board experience, qualifications and skills that are specific to the Company’s accounting, internal control and audit functions. Due to his background, Mr. Josephson also possesses financial reporting expertise and a level of financial sophistication that qualifies him as a financial expert in his role as a member of the Audit Committee.

Dymphna A. Lehane (54) became a director in 2017. Ms. Lehane’s international career includes significant experience dealing with strategic issues andtechnology-led business change at global insurance companies. She is currently the Independent Chair of the Debt Market Integrator, a United Kingdom Cabinet Office venture serving a number of government departments, and has served in such capacity since January 2016 and Chairman of ORIC International, the Insurance Industry Risk Consortium, since December 2015. From 1988 to 2007, she was a Senior Partner at Accenture, including serving as Global Managing Partner, Insurance Industry. She previously served on the boards of Aviva Life and Pensions Insurance Ireland from June 2012 to December 2015 and Aviva Health Insurance Ireland from June 2012 to July 2016, including roles on the Audit and Risk Committees. Ms. Lehane brings to the Board specialized expertise in the global insurance industry and experience in the areas of corporate governance and risk management specific to the financial services industry.

Gary V. Woods (74) became a director in 2000 and has served as Chairman of theOur Board of Directors since 2001. Mr. Woods has been President of McCombs Enterprises, a diversified automotive, energy, real estate and investment holding company, since 1979. He also serves on the boards of directors of the Southwest Research Institute and the San Antonio Cancer Foundation. Mr. Woods brings to the Board an entrepreneurial background with experience in overseeing complex business organizations. As President of McCombs Enterprises, Mr. Woods has successfully funded and promoted numerous growth companies inreflects a diverse array of industries, both domestically and internationally, providing him with the necessaryexperiences, skills and qualificationsbackgrounds. Each director is individually qualified to servemake unique and substantial contributions. This diverse skillset is enhanced by both the fresh perspectives brought by our newer directors, as well as the Chairmanindustry and Company-specific expertise of our longer-tenured directors, who have the experience of guiding our Company through the extended business cycles faced by the insurance industry.

The following chart provides an overview of certain types of knowledge, skills and experiences possessed by one or more of our director nominees and which our Board of Directors believes are relevant to our Company, business and industry, both today and as we execute our long-term business strategy. The chart does not encompass all of the Company’sknowledge, skills and experience of our directors, but rather indicates specific areas of focus or expertise relied on by the Board of Directors.

Director Nominee Biographical Information for the Class III Directors whose Terms Expire in 2019

F. Sedgwick Browne (75) became a director in 1999 and also served as Vice-Chairman of the Company’s board of directors from 2003 until 2007. He retired as counsel at Sidley Austin Brown & Wood LLP (now known as Sidley Austin LLP), a law firm, in 2004. Mr. Browne previously was a partner at Morgan, Lewis & Bockius LLP and prior thereto at Lord Day & Lord, Barrett Smith, where he specialized in the insurance and reinsurance industry. Prior to his retirement and for more than twenty years, Mr. Browne was a trustee and director of the Swiss Reinsurance US Group and of the Winterthur Swiss Insurance US Group. In addition to his historical knowledge of the Company’s operations, Mr. Browne brings to the Board a corporate transactional background that is specific to the Company’s operations in the insurance sector. Mr. Browne also possesses financial reporting expertise and the legal experience and qualifications necessary to guide the Company through many of the regulatory requirements currently imposed on publicly traded companies.

addition, Ms. Nealon served on the board of directors of Cable and Wireless Communications Plc and its predecessor company, Cable and Wireless Plc, from 2005 until 2011. In 2012, Ms. Nealon was named to the board of Health Education England, an executivenon-departmental public body, sponsored by the Department of Health that manages health education in England, where she currently holds the position of Deputy Chair. Ms. Nealon brings to the Board specialized expertise in the areas of corporate governance, compliance and risk management specific to the banking and financial services industries.

Non-EmployeeNON-EMPLOYEE Director CompensationDIRECTOR COMPENSATION

Cash Compensation Program

Ournon-employee directors receive a combination of cash retainers meeting fees and travelspecial meeting fees as described in the following table. In addition, our non-employee directors receive annual grants of equity compensation. We also reimburse our directors for travel, lodging and related expenses incurred in attending our board or committee meetings or for travel related to the Company’s business.

Working with FW Cook, the independent compensation consultant to the Human Resources Committee, our Board reviews compensation on a regular basis to evaluate whether our non-employee director compensation program is market competitive with our peers. Following our 2020 market review of director compensation, in May 2020, our Board implemented the following changes to the program: (1) increased the Chairman of the Board retainer from $50,000 to $125,000 as the competitive study indicated it was significantly below market; and (2) eliminated fees of $2,000 per day for travel to board and committee meetings and for travel related to the Company’s business, and correspondingly increased the annual grants of equity compensation proportionately from $70,000 to $95,000, resulting in no incremental increase to ongoing director compensation. The director compensation program did not otherwise change as compared to 2019.

Beginning in 2018, $40,000 of the Annual Retainer (or $10,000 per quarter) will be paid subject to attendance at Board meetings.

Annual Equity Awards

Each of ournon-employee directors receives an annual fixed-value grant of $70,000 awarded in restricted stock. The awards are granted on the date of our annual general meeting of shareholders that is generally held in May of each year. The awards vest on the third anniversary of the date of the grant. Beginning in 2018, the awards will vest on the day preceding the next annual general meeting of shareholders.

Deferred Compensation Plan

Until December 16, 2013, ournon-employee directors were also entitled to participate in a deferred compensation plan. The plan allowed anon-employee director to defer 0%, 50% or 100% of his or her cash compensation. While no further deferrals were permitted under the plan from and after December 16, 2013, and certain amounts thereunder were paid out prior to the end of 2013, additional deferred amounts remained subject to the terms of the plan. Under the plan, deferred amounts were credited with interest, compounded quarterly at a rate 2% above the prime commercial lending rate. The Company also matched 75% of the deferred amount which was converted into stock units based on the closing price of the Company’s stock on the date that the deferred amount was otherwise earned. Pursuant to the plan, each director was credited with an initial grant of 1,650 stock units. The hypothetical value of a stock unit at any point in time was equal to the market value of the Company’s common stock. Pursuant to the terms of the plan, all remaining amounts were distributed in December of 2017 and were paid in cash.

20172020 Non-Employee Director Compensation

The following table sets forth ournon-employee directors’ 20172020 cash and equity compensation. References next to each director’s name in column (a) refer to the applicable committee legend included in the “Committee Retainers” section of theNon-Employee Director Compensation cash compensation schedule above. The values shown in column (c) represent the U.S. GAAP ASC TOPIC 718 fair value on the grant date.

The following table sets forth the aggregate number of shares of restricted stock appreciation rights ownedheld as of December 31, 2020 by each of ourindividual who served as a non-employee directors on December 31, 2017:director during 2020:

Director Stock Ownership

All of ournon-employee directors are expected to comply with the Company’s Equity Ownership Guidelines that are discussed beginning on page 33.51. The guideline ownership level requires eachnon-employee director to hold equity having a value equal to or greater than threefive times the annual retainer they received for service on the Company’s Board of Directors in the preceding year.Non-employee directors must hold all shares earned through service on the Board of Directors until they meet the guideline ownership level. Compliance is tested as of the first business day of the second quarter each year. As of April 1, 2017,the Record Date, all of ournon-employee directors either held the requisite number of shares or were in compliance withsubject to the Company’s Equity Ownership Guidelines.100% retention requirement.

In addition, all of ournon-employee directors are subject to the Company’s Insider Trading Policy that, among other things, prohibits pledging and hedging transactions involving the Company’s equity securities and further prohibits directly or indirectly pledging a significant number of our equity securities. The Company’s Insider Trading Policy is discussed beginning on page 34.52.

PROPOSAL 2

2: ADVISORY VOTE ON THE COMPENSATION OF THE NAMED EXECUTIVE OFFICERS AS DISCLOSED IN THIS PROXY STATEMENT

The Dodd-Frank Wall Street Reform and Consumer ProtectionSection 14A of the Exchange Act enacted in July 2010 (the “Dodd-Frank Act”), included a requirementrequires that companies provide shareholders with an opportunity to vote on an advisory,non-binding basis on the compensation of the Company’s Named Executive Officers, as disclosed in the Compensation Discussion and Analysis and related tables in thethis proxy statement. This vote is on the compensation reported for the NEOs in the proxy for the prior year and is commonly referred to as “say on pay.” Consistent with the preference expressed by our shareholders at our 2017 annual general meeting, our Board of Directors has determined that we will include a vote to approve, on an advisory, non-bindingbasis, our executive compensation in our proxy materials every year until the next required advisory vote to approve the frequency of an advisory vote on executive compensation, which will occur no later than our 2023 annual general meeting.

As discussed more fully in the Executive Summary of the Compensation Discussion and Analysis section which begins on page 2033 and the discussion that follows it, the Company’s compensation program is designed to link pay to both business and individual performance and is intended both to retain superior, productive employees and to attract new talent necessary to continue the Company’s profitable growth. The program is designed to align the interests and motivations of our executives with the creation and protection of shareholder value. The program includes three main components – base salary, annual incentive awards and long-term incentive awards.

We consider growth in book value per share, inclusive of cash dividends paid to our shareholders, to be the most comprehensive assessment of our ability to create shareholder value. Growth in book value per share is achieved through a combination of underwriting income, total return on our invested assets and capital management. Since 2002, the Company’s book value per share has grown at a compounded growth rate of 9.4% per year inclusive of both the ordinary and extraordinary dividends paid during such period. The Company believes that its NEOs were instrumental in achieving these results and the compensation packages designed for them are intended both to reward them for their current achievements and to motivate them to continue to excel in the future. We believe our record continues to compare well with our peers in terms of value creation, particularly given the extraordinary economic and market conditions facing our industry over the past several years. Accordingly, the Company requests shareholder approval of the following resolution:

“RESOLVED, that the Company’s shareholders approve, on an advisory,non-binding basis, the compensation of the Named Executive Officers as disclosed in the Compensation Discussion and Analysis, compensation tables and narrative discussion included herein.”

An advisory vote is not binding upon the Company. However, the Human Resources Committee, which is responsible for designing and administering the Company’s executive compensation program, values the opinions expressed by shareholders and will consider the outcome of the vote when making future compensation decisions related to the Company’s NEOs.

Required Vote and Board Recommendation

The approval, on an advisory, non-binding basis, of the compensation of our Named Executive Officers will be decided by an ordinary resolution; that is a resolution duly adopted by the Board of Directors, which has already occurred, and then approved by shareholders with a simple majority of votes cast in person or by proxy. Votes may be cast in favor of or against this proposal or a shareholder may abstain from voting. Abstentions and broker non-votes will not count as votes cast and, therefore, will have no effect on the outcome of this proposal.

THE BOARD OF DIRECTORS RECOMMENDS THAT SHAREHOLDERS VOTE TO

APPROVE THIS PROPOSAL. IT IS THE INTENTION OF THE PROXIES NAMED

IN THE FORM OF THE PROXY THAT ACCOMPANIES THIS PROXY STATEMENT TO VOTE FOR

THE APPROVAL OF SUCH PROPOSAL.

NAMED EXECUTIVE OFFICERSCOMPENSATION DISCUSSION AND ANALYSIS

This Compensation Discussion and Analysis (“Business ExperienceCD&A”) discusses our compensation policies and determinations that applied to the following named executive officers, or NEOs:

(1) On July 2, 2020, the Company announced the anticipated departure of NamedMr. Bullock as Executive Vice President and Chief Financial Officer of the Company. Mr. Bullock continued to serve as Executive Vice President and Chief Financial Officer through March 15, 2021 and will remain employed in an advisory capacity through March 31, 2021. On March 16, 2021, Scott Kirk replaced Mr. Bullock as the Company’s Chief Financial Officer.

(2) On June 15, 2020, the Company appointed Timothy D. Carter as Chief Underwriting Officer, succeeding Axel Schmidt who would remain employed in an advisory capacity through March 31, 2021.

(3) Allison D. Kiene joined the Company as Senior Vice President and General Counsel on October 1, 2020.

Information About Our Executive Officers

Mark E. Watson III (53) has beenOur executive officers, along with each such person’s age, present title and certain biographical information, is included below. Also included is information regarding our former Chief Financial Officer, Mr. Bullock.

Kevin J. Rehnberg (57) is the Chief Executive Officer, effective as of February 18, 2020. He had previously served as the Interim President and Chief Executive Officer ofsince November 4, 2019. Prior thereto, Mr. Rehnberg served as President, Argo Group U.S., Inc., Head of the Americas and Chief Administrative Officer since January 2000. A description2019. From March 2013 to January 2019, Mr. Rehnberg was President of Argo’s U.S. Operations, overseeing all activities of Argo’s U.S.-based business segments. Prior to joining the Company, Mr. Watson’s business experience can be found beginning on page 15Rehnberg served as executive vice president for specialty lines at OneBeacon Insurance, where he oversaw specialty underwriting operations and acquired and built new lines of specialty business. Prior to that, he held positions at the biographical information for the three Class I directors whose terms expire in 2020 is set forth.St. Paul Travelers Companies, Liberty International and Chubb Corporation. He has a bachelor’s degree from Princeton University.

Jay S. Bullock (53)Scott Kirk (47) has been the Chief Financial Officer of Argo Group since March 16, 2021. He was previously employed by Aspen Insurance Holdings Limited (“Aspen”), a global property and casualty insurance and reinsurance company, holding various roles beginning in 2007 and most recently served as Aspen’s Group Chief Financial Officer from 2014 until April 2020. Prior to joining Aspen, Mr. Kirk worked at Endurance Specialty Holdings Ltd. between 2002 and 2007, holding several senior finance roles. Previously, Mr. Kirk was at Trenwick International Ltd. in London working in finance and treasury. Mr. Kirk began his career as an auditor at KPMG, Brisbane and is a member of the Institutes of Chartered Accountants in both England and Wales and Australia.

Jay S. Bullock (56) was Chief Financial Officer of Argo Group from May 2008.2008 until March 15, 2021. He joined Argo Group from Bear Stearns & Co. Inc. where he was a Senior Managing Director and Head of Bear Stearns’ Insurance Investment Banking Group. While at Bear Stearns, Mr. Bullock focused on the insurance sector. In this role, he advised on company acquisitions, mergers and sales as well as all forms of public and private financings and restructurings. During this period, he was also an advisor to Argo Group on a number of transactions. Prior to joining Bear Stearns in 2000, Mr. Bullock was a Managing Director at First Union Securities. He is an honors graduate of Southern Methodist University and received his MBA from The McColl School of Business, Queen’s College, Charlotte, North Carolina. Mr. Bullock also holds the designation of Certified Public Accountant (CPA).

Jose A. Hernandez (52) has been Head of International of Argo Group since October 2016. Prior to joining the Company, Mr. Hernandez most recently served as president and chief executive officer of American International Group’s Asia Pacific region. Mr. Hernandez spent more than 20 years with American International Group in a number of senior leadership roles in both the consumer and commercial segments. He has expertise in field operations, distribution, underwriting, claims, strategic planning and management. Mr. Hernandez has a bachelor of science degree in Marketing and Management from Bentley University and a master in business administration degree with a concentration in insurance from the College of Insurance in New York.

Kevin J. RehnbergTimothy D. Carter (54) has been President of Argo Group’s U.S. Operations since March 2013. Prior to joining the Company, Mr. Rehnberg served as executive vice president for specialty lines at OneBeacon Insurance where he oversaw specialty business. Mr. Rehnberg began his career at Chubb in 1986 and he held a number of roles with increasing responsibility at Chubb Atlantic, Liberty, St. Paul and St. Paul Travelers through 2005. More recently, he served as CEO of Consultants in Laboratory Medicine of Greater Toledo, Inc. Mr. Rehnberg has a bachelor’s degree in History from Princeton University.

Axel Schmidt (61) has beenbecame Chief Underwriting Officer of Argo Group since August 2014. He camein June 2020. Prior to joining Argo Group, from Aviva where heMr. Carter served as Chief Underwriting Officer and President of Portfolio Solutions for the company’s UK/Ireland business across personal, commercial and corporate/specialty lines and also as Aviva’s global practice leader for underwriting, products, pricing and claims. Prior to joining Aviva, Mr. SchmidtGlobal Commercial Insurance at AIG. He previously spent 2017 years at Zurich in their international businessInsurance where he held a number of senior underwriting and management positions, including Deputy Chief Executive Officer/CUO for their corporate business in Europe/UKUnderwriting Officer of both North America and Underwriting Director for their global corporate business. He also servedEurope. Mr. Carter started his career as a member of Zurich’s Group Underwriting and Group Reinsurance Board. Prior to joining Zurich, Mr. Schmidt spent 2 yearsconsulting actuary at Gerling Global Re as an underwriter. Mr. SchmidtWatson Wyatt. He graduated from Westphalian WilhelmsNottingham University in Munster, Germanythe United Kingdom with a degree in Law Studies. HeMathematics and is a Fellow of the Institute of Actuaries.

Matthew J. Harris (51) became Head of International Operations of Argo Group effective January 1, 2019. Prior to then, Mr. Harris had served as Head of Europe, Middle East and Asia of Argo Group since July 2017. Mr. Harris has more than 25 years of insurance experience with expertise in multiple operational disciplines. Mr. Harris has successfully undertaken senior management assignments across multiple distribution channels and product segments. Prior to joining the Company, Mr. Harris spent nearly 10 years at American International Group (“AIG”) where, since January 2015, he was the Chief Executive Officer of AIG Asia Pacific Pte Ltd. During his tenure at AIG, Harris also earnedled South East Asia Country Operations and served as Chief Executive Officer of Malaysia Insurance and Chief Executive Officer of Chartis New Zealand (formerly American International Group New Zealand).

Allison D. Kiene (54) has served as the Company’s General Counsel since October 2020. She came to Argo Group from Sompo International Holdings Ltd., a Juris Doctoratewholly-owned subsidiary of Sompo Holdings, Inc. established in 2017 as the result of the acquisition of Endurance Specialty Holdings Ltd. (“ENH”), where she served as Assistant General Counsel and Chief Compliance Officer. Ms. Kiene joined ENH following ENH’s acquisition of Montpelier Re Holdings Ltd. (“MRH”) in July 2015. From 2007- 2015, Ms. Kiene served as Assistant General Counsel, Assistant Group Secretary and Head of Group Compliance Officer for MRH. While at MRH, Ms. Kiene also served as General Counsel and Chief Compliance Officer for MRH’s investment management company, Blue Capital Management Ltd. Ms. Kiene received her Bachelor of Science degree in Pharmacy from the State Supreme CourtUniversity of Connecticut School of Pharmacy and her Juris Doctor degree from the University of Connecticut School of Law. Ms. Kiene is admitted to the Bar in Dusseldorf, Germany.Connecticut, Massachusetts, and New York.

Andrew M. Borst (47) became the Chief Administrative Officer of Argo Group in June 2020 and was designated as an executive officer in February 2021. He had previously served as the Chief Administrative Officer - International Operations of Argo Group from April 2019 to June 2020, and Chief Administrative Officer – US Operations of Argo Group US, Inc. from August 2018 to April 2019. Mr. Borst joined the Company in March 2014 and led the Specialty Programs business unit for Argo Group US, Inc. until August 2018. Prior to joining the Company, Mr. Borst spent eleven years with OneBeacon Insurance Company in various management and finance roles as well as six years with Travelers Property Casualty Corporation where he graduated from its Financial Management Development Program in 1999. He graduated with honors from Boston University School of Management with a Bachelor of Science in business administration with concentrations in Finance and Management Information Systems.

COMPENSATION OF EXECUTIVE OFFICERSExecutive Summary

Business Overview

Argo is an underwriter of specialty insurance products in the property and casualty market, with a focus on U.S. domiciled risks. Argo has been a consistent leader in U.S. excess and surplus lines and the specialty admitted market for over two decades, and also has leading platforms at Lloyd’s and in the Bermuda Insurance market. We target niches where we can develop a meaningful position and where we believe we will generate superior underwriting profits through our industry expertise and strong underwriting and claims capabilities. The Company operates in two segments, U.S. Operations and International Operations.

2020 Company Performance and Strategy

During 2020, Argo made significant progress in a number of strategic priorities and enhancing our business profile as a U.S. focused specialty insurer, while working towards our objective of achieving double digit returns on common equity. These strategic achievements focused on realigning, simplifying and ultimately positioning the business for future profitability, all of which were accomplished as the Company worked to minimize the impact of COVID-19 on its 2020 operations. Key achievements included:

Repositioned Business Units for profitability

Implemented Expense Reduction Initiatives