May 2019

1. Hamilton Insurance Group May 2019

2. 3 10 14 20 22 INTRODUCTION AND HIGHLIGHTS BOARD OF DIRECTORS AND EXECUTIVE COMMITEE INSURANCE AND REINSURANCE OPERATIONS TWO SIGMA APPENDIX Table of Contents

3. Introduction

4. OUR MISSION We’re writing the future of risk. Be smart. Be sensible. Be open. And above all else… Be more. FIRST PRINCIPLES STRATEGY STATEMENT We will create a unique, diversified insurance company embracing data science and technology, on both sides of the balance sheet, to create superior shareholder value over the long term. Mission and First Principles EMPLOYEE VALUE PROPOSITION In good company. DIVERSITY & INCLUSION STATEMENT Open minds open doors.

5. Hamilton & Two Sigma: A Powerful Partnership • Hamilton was launched in December 2013 by team led by insurance industry veteran Brian Duperreault. • Our Group CEO is Pina Albo. • We’re executing a strategy to leverage analytics and research to create superior underwriting and investment value for our clients and shareholders. • We’re differentiated by: • startup mindset coupled with a deeply experienced management team • our commitment to leveraging technology and data science • our relationship with Two Sigma, a technology and investment company • no legacy (financial our or systems) issues • As of November 30, 2018, Hamilton has over $1.8 billion in shareholders’ equity. A New York-based technology and investment company with unique experience and capabilities in the area of advanced analytics, which it applies to data-driven investing and underwriting (through Two Sigma Insurance Quantified). Assets under management of over $60 billion. Generated positive alpha and net returns every year since inception—17 consecutive years. 1550+ employees, two thirds of whom are modelers and engineers. Has distinguished itself as an innovator in technology and investment management.

6. Platform Overview • Established book of business in sixth year of growth • Shareholder’s equity over $1.6 billion at November 30, 2018 • Wrote over $350 million of gross premiums in 2017; forecast to write approximately $360 million in 2018 • Cumulative net earnings of over $1 billion* • Notable and diverse client base • Growing third party capital platform • Rated “A-” by A.M. Best • Hamilton Underwriting Limited, a Lloyd’s Managing Agency, controls Syndicate 3334 • Wrote over $130 million of gross premiums in 2017; forecast to write approximately $175 million in 2019 • Benefits from Lloyd’s ratings from A.M. Best “A” (Excellent); Fitch “AA-” (Very Strong); and S&P “A+” (Strong) • Joint venture between Hamilton, AIG and Two Sigma formed in 2016 • Building a market-leading, technology-based platform in the $150 billion Small to Medium Enterprise (SME) market • Led by CEO James Hobson, former COO of OnDeck Capital • Represents an unprecedented partnership that leverages data science, technology, brand awareness and a small business pipeline • Partnership with Hamilton is unique in the industry • Manages majority of Hamilton’s capital in its proprietary funds • Leverages data analytics and modeling skills to advance the science of underwriting risk • Dedicated staff at Two Sigma Insurance Quantified (TSIQ) work closely with Attune and Hamilton on data science and other strategic projects • Entities affiliated with principals of Two Sigma are significant shareholders at Hamilton * Stated on a legal entity basis. Net earnings excluding intercompany reinsurance is higher. BOOK VALUE PER SHARE

7. A transformative deal for Hamilton • On March 14, 2019, Hamilton signed a Sale and Purchase Agreement to acquire Pembroke Managing Agency Limited (Pembroke), Ironshore Europe (IEDAC) and related entities, including MGAs in the US and Dubai, from Liberty Mutual Group. • Upon closing later this year, this deal will: • almost double our total premium base to ~$1 billion; • more than double our talent pool, with the majority of new employees being based in London; • provide a Dublin-based carrier with a UK branch, enabling flexibility and strategic optionality; • establish platforms that support the execution of Hamilton’s growth strategy, including additional fee-based income and US E&S licenses; • provide additional licenses and platforms with which to expand our reinsurance operations; and • provide a larger platform to leverage our existing technology and build out our data science and analytics capabilities.

8. Hamilton: One of a Kind • Management • Renowned Board of Directors, with diverse backgrounds • Proven management team • Strategy • Uniquely embraces data science and technology on both sides of the balance sheet • Early adopter of insurtech through partnership with Two Sigma • Nimble organizational structure in Bermuda and Lloyd’s markets; accesses US insurance through Attune • Performance • Favorable loss results following 2017 storm season; praised for rapid, client-focused response  • Proprietary AI-based analytics  • Superior financial strength • Meeting or exceeding profitability expectations — targets positive returns for both underwriting and investment  • Disciplined growth • Poised to continue to generate superior returns • Efficiency in operating systems across the group • Talent • Highly skilled, cross-functional and collaborative teams • Engaged employees committed to company mission  • Expert risk management • Consistent performance through market volatility

9. CONSOLIDATED SHAREHOLDERS’ EQUITY BOOK VALUE PER SHARE BOOK VALUE PER SHARE CONSOLIDATED SHAREHOLDERS’ EQUITY (MILLIONS) Hamilton Group Growth in BV and SE $9.83 796 $12.83 $15.43 $16.22 $16.07 1,565 1,655 1,628 1,047 Hamilton was funded pursuant to a private placement offering at $10.00 per share on December 23, 2013.  Certain founding shareholders exercised a $250 million greenshoe right, effective January 1, 2015.  9

10. Board of Directors and Executive Committee

11. Renowned Leadership in Governance BOARD OF DIRECTORS • Pina AlboCEO, Hamilton Insurance Group • Worked 25 years at Munich Re, most recently sitting on the board of management with responsibility for Europe and Latin America (2014–2017) • Practiced law at Tory’s, a leading Canadian law firm • Recognized as advocate for diversity and inclusion in the workplace • Member of board of directors for IFG Companies • Bill FredaChairman, Hamilton Insurance Group; Chairman, Audit Committee • Retired as Vice Chairman, Deloitte LLP after a distinguished 40-year career with the firm • Member of the Board of Directors of The Guardian Insurance Company of America and State Street Corporation StevePacala Frederick D. Petrie Professor of Ecology and Evolutionary Biology at Princeton University; Director of the Princeton Environmental Institute Recipient of the MacArthur Award, Mercer Award and the David Starr Jordan Prize Member of the American Academy of Arts and Sciences and the National Academy ofSciences • David SiegelChairman, Compensation Committee • Co-founder of Two Sigma and former Chief Technology Officer and Managing Director, Tudor Investment Corporation • First Chief Information Officer, D.E. Shaw & Co. • A graduate of Princeton University who holds a PhD in computer science from the Massachusetts Institute of Technology (MIT) • Board memberships include the Scratch Foundation, NYC First, NAF, and the Cornell Tech Board of Overseers; serves as a trustee of Carnegie Hall • Joan Lamm-Tennant • Chief Executive Officer of Blue Marble Microinsurance, an insurance industry collaborative announced in January 2015 to provide protection to the underserved • Prior to Blue Marble, served as Global Chief Economist and Risk Strategist, Guy Carpenter & Company, LLC • Faculty Member of the Wharton School, University of Pennsylvania PaulineRichards COO of Armour Group Holdings Limited Former CFO of Lombard Odier Darier Hentsch (Bermuda) Member of the Boards of Wyndham Worldwide and Apollo Global Management and a past member of Cendant Corporation and ButterfieldBank • John OverdeckChairman, Underwriting and Risk Committee • Co-founder of Two Sigma and former Managing Director, D.E. Shaw & Co. • International Mathematics Olympiad Silver Medalist for the US who holds a B.S. in Mathematics (with distinction) and an M.S. in Statistics from Stanford University • Serves on the Boards of the Robin Hood Foundation, the Institute for Advanced Study and, as Vice Chair, of the National Museum of Mathematics • David BrownChairman, Finance and Governance Committee • Founder & Chief Executive Officer of Flagstone Re 2005–2012 • Chief Executive Officer, Centre Solutions 1994–1997 Former Partner, EY • Chairman of the Board of Bermuda Stock Exchange David Siegel – Chairman, CompensationCommittee Co-founder of Two Sigma and former Chief Technology Officer and Managing Director, Tudor InvestmentCorporation First Chief Information Officer, D.E. Shaw & Co. A graduate of Princeton University who holds a PhD in computer science from the Massachusetts Institute of Technology (MIT) Board memberships include the Scratch Foundation, NYC First, NAF, and the Cornell Tech Board of Overseers; serves as a trustee of Carnegie Hall

12. Renowned Leadership in Governance BOARD OF DIRECTORS (continued) • Peter Koffler • Peter Koffler is a Senior Managing Director of The Blackstone Group and General Counsel for the Hedge Fund Solutions Group.  • Prior to joining Blackstone in 2006, Peter served as General Counsel and Chief Compliance Officer of Twenty-First Securities Corporation, an institutional trading and investment firm. He began his legal career at Baer Marks & Upham.   • Peter received a BA from the State University of New York at Binghamton. He received a JD, with honors, from Hofstra University School of Law, where he served as an editor of the Law Review.  • Russ Fradin • Lead Independent Director of Best Buy Co., Inc., and Operating Partner of private equity firm Clayton, Dubilier & Rice • Formerly President and Chief Executive Officer of SunGard Data Systems; Chief Executive Officer of the BISYS Group; and Chairman and Chief Executive Officer of Aon Hewitt, where he oversaw merger between Aon Consulting and Hewitt Associates • Held senior positions at Automatic Data Processing and McKinsey & Company • Earned MBA from Harvard Business School and BSc in Economics and Finance from The Wharton School at the University of Pennsylvania • Charles Collis • Charles Collis is a director in the corporate department in the Bermuda office of Conyers Dill & Pearman. He also is head of the Bermuda Insurance Practice. • Charles specializes in insurance and reinsurance, advising on corporate and regulatory matters. He has advised on the establishment of numerous captive insurance companies, as well as commercial reinsurance companies. Charles also specializes in insurance-linked securities, a focus he has sharpened as a result of the convergence of insurance and capital markets. More specifically, he has conducted a number of insurance securitizations and transformation transactions using special purpose vehicles, traditional reinsurance companies and segregated account companies. • Charles earned a B.A. (Honors) from the University of Toronto, and an LLB from University College, London. He is a member of the bar in Bermuda, British Virgin Islands, and England and Wales. • Steve Pacala • Frederick D. Petrie Professor of Ecology and Evolutionary Biology at Princeton University; Director of the Princeton Environmental Institute • Recipient of the MacArthur Award, Mercer Award and the David Starr Jordan Prize • Member of the American Academy of Arts and Sciences and the National Academy of Sciences • Pauline Richards • COO of Armour Group Holdings Limited • Former CFO of Lombard Odier Darier Hentsch (Bermuda) • Member of the Boards of Wyndham Worldwide and Apollo Global Management and a past member of Cendant Corporation and Butterfield Bank

13. Pina Albo – CEO, Hamilton Insurance Group • Worked 25 years at Munich Re, most recently on the Board of Management with responsibility for Europe and Latin America (2014-2017) • Practiced law at Tory’s, a leading Canadian law firm • Recognized as advocate for diversity and inclusion in the workplace • Member of Board of Directors for IFG Companies • Kathleen Reardon – CEO, Hamilton Re • Member of the founding management team, with more than 20 years’ experience in the insurance industry • Fellow of the Casualty Actuarial Society • 18 years at ACE (f.k.a. CIGNA) in various positions, including CUO International of ACE Tempest Re Bermuda (2005-2012) • Vice Chair, Reinsurance Association of America • Chair, Women in Reinsurance (Bermuda) • Peter Barrett – Global Head, Specialty Insurance • Former Chairman of Lloyd’s insurance broker Bell & Clements where he started his career in 1976 • Board member of the American Association of Managing General Agents (AAMGA) • National Association of Surplus Lines Offices (NAPSLO) committee member Executive Committee • Pete Skerlj – Group CRO • Member of the founding management team, with more than 20 years’ experience in risk and analytics • Fellow of the Casualty Actuarial Society • As a Catastrophe Modeling Consultant at Q Re, created a property retro portfolio management and pricing framework • Previous experience includes senior positions with Lancashire Insurance, Partner Re Global and Applied Research Associates • Jonathan Reiss – Group CFO • Member of the founding management team, with 26 years’ experience in the insurance industry • Insurance Practice Leader at EY Bermuda (2006 – 2012) • 19 years at EY, including 12 at Partner level dedicated to serving insurance industry clients • Trustee of the Bermuda Institute of Ocean Sciences • Wendy Davis Johnson – Chief Communications & Culture Officer • Over 25 years' experience in corporate communications and brand development • Former SVP, Global Communications, ACE Group (now Chubb) • Member of the Insurance Development Forum's Microinsurance Working Group • Chair of Hamilton’s Community Giving Committee • Master of Liberal Arts, Journalism, Harvard University • Gemma Carreiro – Group General Counsel • Associate General Counsel at PartnerRe (2014 – 2017) • Senior Associate at Conyers Dill & Pearman Limited (2007 – 2014) Associate at Cox Hallett Wilkinson (2005 – 2007) • Member of the Bermuda Bar Association • Daniel Fisher – Group Head of HR • Over 20 years' HR experience, 13 years of which were at Munich Re, where his increasingly senior positions included HR Director (UK), Regional Head of HR (North America), and Global Head of HR Strategy • Experience also includes Global Head of HR at International Swaps & Derivatives Association and consultant with KPMG • Fellow of the Chartered Institute of Personnel & Development • Michael Papamichael – Group Corporate Development • Former SVP, Global Planning Officer, Corporate Development & Investor Relations at Sirius Group • 17 years of experience in the insurance industry • Earned an MBA, summa cum laude with honors and distinction, from Columbia Business School and an Economics degree, magna cum laude, from Boston College

14. Insurance and Reinsurance Operations

15. OVERVIEW • During the period July 2012 (inception) to November 30, 2018, Hamilton Re earned over $1.1 billion of net income and paid dividends of $282 million to Hamilton Insurance Group. • Shareholder’s equity over $1.6 billion as of November 30, 2018. • Maintains a conservative risk profile, limiting PML to 15% of shareholder’s equity in the US and 10% for the rest of the world. • Through strategic relationship with AIG, provided with opportunity to participate in increased volume of AIG's ceded reinsurance. • Manages risk exposures through a combination of third-party models and HARP (Hamilton Analytics and Risk Platform), a proprietary risk management platform that: • is a collection of software tools used to build, optimize and analyze Hamilton Re’s risk portfolio; • simulates 200,000 iterations of loss scenarios over a multi-year window; and  • is fully embedded in the frontline risk selection and pricing process. • In July 2018, launched Beam, Hamilton’s bespoke deal management system.  • In November 2018, in direct response to clients’ interest in multiline support, established Risk XS book. • In March 2019, secured $65m of collateralized capacity for our special purpose sidecar Turing Re II to support our global property reinsurance portfolio.  Kathleen Reardon CEO, Hamilton Re Hamilton Re GROSS PREMIUMS WRITTEN (GPW)(1) GPW ($mm) (1) For fiscal year period 15

16. 2018 YEAR OF ACCOUNT OUR PORTFOLIO SPECIALTY REINSURANCE SPLIT BY CLASS SPLIT BY SEGMENT PROPERTY REINSURANCE CASUALTY REINSURANCE Hamilton Re SPLIT BY REGION SPLIT BY CLASS PROPERTY D&F INSURANCE EXCESS CASUALTY INSURANCE SPLIT BY CLASS SPLIT BY CLASS 16

17. OVERVIEW Peter Barrett, Global Head, Specialty Insurance, will hold the position of Interim CEO at Lloyd’s. The combined operations from Janus will double Hamilton’s employee base, with concentration in London, and provide meaningful scale at Lloyd’s as well as access to non Lloyd’s, EU and US E&S business. The portfolio of business underwritten by Pembroke’s Syndicate 4000 is highly complementary to Hamilton’s Syndicate 3334. Now in its fourth underwriting year, Hamilton Underwriting Limited maintains a stamp capacity of $175 million after exiting Professional Indemnity and Contingency lines in 2018. In 2017, Hamilton at Lloyd’s completed the Reinsurance to Close (RITC) to transfer legacy business inherited from the 2015 acquisition of Sportscover. Peter Barrett Global Head, Specialty Insurance Hamilton at Lloyd’s GROSS PREMIUMS WRITTEN (GPW) GPW ($mm) $83 $129 $175 $175 17

18. 2018 YEAR OF ACCOUNT OUR PORTFOLIO TREATYREINSURANCE SPLIT BY CLASS SPLIT BY TERRITORY SPECIALTY DIRECT FACULATIVE PROPERTY Hamilton at Lloyd’s SPLIT BY TERRITORY SPLIT BY CLASS SPACE, AVIATION and MARINE & ENERGY LIABILITY CASUALTY SPLIT BY CLASS SPLIT BY CLASS 18

19. Attune is building a market-leading, technology-based platform in the $150 billion Small to Medium Enterprise (SME) market Represents an unprecedented partnership that leverages data science, technology, brand awareness and a small business pipeline

20. Two Sigma

21. Two Sigma1 is a process-driven, systematic investment manager primarily focused on global liquid markets. Two Sigma applies its technology and expertise in financial markets to seek to consistently generate uncorrelated alpha across a wide range of market conditions. WHERE WE ARE TODAY • Computing Power and Data • 7,000+ servers in computing environment, with 335,000+ vCPUs and 2,232 terabytes of memory • 42+ petabytes of data and growing • 10K+ data sources • Human Capital • 4,500+ person years of R&D • Professional represent 80+ countries with ~60% coming from outside of finance • >95% voluntary employee retention, since inception • Performance5 • 17 consecutive years of positive alpha • 99.5% of investors have earned positive alpha • 81.9% positive (net alpha) product quarters WHAT WE DO Deploy and seek to continuously improve intelligent investment management systems first created in 2001 Manage approximately $60.1 billion of assets for a global, diversified client base in absolute return and benchmark-relative investment mandates2 Trade equities, futures, FX and derivatives in 40+ countries utilizing a highly diversified set of systematic strategies Tap the talents of 1,550+ employees headquartered in New York with additional offices in Houston, London, Hong Kong, and Japan2 Operate as a Registered Investment Adviser with the SEC3 and a Qualified Professional Asset Manager4 Note: For illustration purposes only. Not an offer to buy or sell securities. Two Sigma may modify its investment approach and portfolio parameters in the future in any manner that it believes is consistent with its fiduciary duty to its clients. There is no guarantee that Two Sigma or its products will be successful in achieving any or all of their investment objectives. Moreover, all investments involve some degree of risk, not all of which will be successfully mitigated. (1)As referenced  on this slide, “Two Sigma” or “the Firm” generally refers collectively to Two Sigma Investments, LP and Two Sigma Advisers, LP and their affiliates. (2) AuM and employee count are approximate as of March 1, 2019. AuM has been adjusted downward to account for investments by (or exposure to) (i) a product in another product where both products are advised by the same manager and (ii) a TSI product in a TSA product and vice versa. (3) Two Sigma Investments, LP and Two Sigma Advisers, LP are registered with the U.S. Securities and Exchange Commission (the “SEC”). Registration does not imply review, endorsement or approval by the SEC. (4) QPAM designation applicable to Two Sigma Advisers, LP only. (5) Net alpha” is measured against zero for absolute return products and against the applicable benchmark for beta-1 products and is net of management fees, incentive allocations and all other fund and trading expenses, in each case, to the extent applicable.  Statistics regarding investor and product performance are dollar-weighted by AuM as of December 31, 2018. Performance statistics only include performance of unaffiliated investors. “Net alpha product quarters” is an asset weighted figure derived by (i) taking the sum of the average notional AuM of each Two Sigma-managed product group by quarter and (ii) dividing the sum of the average notional AuM for the positive net alpha product quarters by (i). . 21

22. 20 22 FINANCIAL HIGHLIGHTS CORPORATE ORGANIZATIONAL CHARTS Appendix

23. CONSOLIDATED BALANCE SHEETS Hamilton Insurance Group

24. CONSOLIDATED BALANCE SHEETS Hamilton Re

25. Corporate Organization Chart • Each entity in the chart is owned 100% directly or indirectly by Hamilton Insurance Group, Ltd., unless indicated otherwise • * Hamilton U.S. Holdings II, Inc. has a 33.33% interest in Attune Holdings, LLC, as part of a joint venture arrangement between Hamilton, AIG and Two Sigma • ** Turing Re, Ltd. is a Bermuda-registered special purpose insurer that is licensed as a segregated accounts company. Hamilton Re owns 1 common share of Turing Re, representing 100% of the voting capital. Non-voting preference shares are issued to outside investors, the proceeds of which are used to reinsure the risk obligations of Hamilton Re on a fully collateralized basis.

26. Wellesley House North, 1st Floor 90 Pitts Bay Road Pembroke HM08 Bermuda +1 (441) 405-5200 www.hamiltongroup.com