HAMILTON INSURANCE

GROUPMARCH 2017

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INTRODUCTION AND HIGHLIGHTS

BOARD OF DIRECTORS AND EXECUTIVE COMMITTEE

INSURANCE AND REINSURANCE OPERATIONS

TWO SIGMA

APPENDIX

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Table of Contents

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Introduction and Highlights

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MISSION: WE’RE WRITING THE FUTURE OF RISK

We’re a Bermuda-based holding company for insurance and reinsurance operations doing business on a

worldwide basis.

WHAT YOU SHOULD KNOW ABOUT HAMILTON

We’re executing a strategy to leverage analytics and research to create superior underwriting and investment

value for our clients and shareholders.

Hamilton was launched in December 2013 by investors led by insurance industry veteran Brian Duperreault.

As of December 31, 2016, Hamilton has over $1.6 billion in shareholders’ equity.

We’re differentiated by: Experienced, successful leadership and management

Our relationship with Two Sigma, a technology and investment company

No legacy (financial or systems) issues

Hamilton Insurance Group

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A Powerful Partnership

BRIAN DUPERREAULT

Forty year illustrious industry career includes serving as President & CEO, Marsh & McLennan Companies; non Executive Chairman of ACE Limited, and CEO and President of ACE Limited; various senior executive positions at American International Group (AIG)

Board positions include Attune, Blue Marble Microinsurance, International Insurance Society, and IESE Business School

Credited by the Insurance Hall of Fame with facilitating the transformation of Bermuda from a small, reinsurance-focused market into a global insurance center

A New York-based technology and investment company with unique experience and capabilities in the area of advanced analytics which they apply to data-driven investing

Assets under management of over $41 billion

Generated positive alpha and net returns every year since inception—15 consecutive years

1,100+ employees, two thirds of whom are modelers

Has distinguished itself as an innovator and a leader in investment management

Hamilton combines distinguished, experienced management and a high-

performing quantitative partner to grow its business and deliver superior

value to its clients and shareholders.

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Hamilton Today

Led by industry renowned management and Board of Directors

Committed to our long-term strategy

Superior financial strength

Meets or exceeds profitability expectations

Expert risk management

Consistent performance through severe market volatility

Disciplined growth

Attracts exceptional talent

Unique partnership with Two Sigma, a leading technology and investment company

Poised to continue to generate superior returns

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Hamilton Platform

Hamilton Underwriting Limited,

a Lloyd’s Managing Agency,

controls Syndicate 3334

Approved by Lloyd’s to write

$150 million of premiums for the

2017 Year of Account and to

add two new lines of business

– Marine Liability and War &

Terror.

Benefits from Lloyd’s ratings

from A.M. Best “A” (Excellent);

S&P “A+” (Strong); and Fitch

“AA-” (Very Strong)

Aims to improve transaction

efficiency and underwriting

results by leveraging cutting-

edge analytical technology

Partners with AIG and Two

Sigma through Attune, a

technology platform dedicated

to small commercial insurance

Benefits from Hamilton’s A.M.

Best Group Rating of “A-” and

Financial Size Category of “XIV”

Hamilton leverages Two Sigma’s data analytics and modeling skills to advance the science of underwriting risk

Manages majority of Hamilton’s invested assets in its proprietary funds

Entities affiliated with principals of Two Sigma are significant shareholders at Hamilton

Has established TSIQ (Two Sigma Insurance Quantified) to dedicate staff to Hamilton data science projects

Partnership with Hamilton

Established book of business in

fifth year of growth; produced

underwriting profit every year

since inception

Shareholder’s equity over $1.5

billion at December 31, 2016

Wrote over $250 million of gross

premiums in 2016; forecast to

write approximately $290 million

in 2017

Bermuda-based Class 4

property and casualty (re)insurer

Rated “A-” (Excellent) with a

stable outlook by A.M. Best

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Hamilton’s Growth in BV and SE

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

BOOK VALUE PER SHARE CONSOLIDATED SHAREHOLDERS’ EQUITY

$15.91 $16.01 $16.22 $1,632 $1,655$1,621

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Board of Directors and Executive Committee

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Industry-Renowned Leadership

BOARD OF DIRECTORS

David Brown – Chairman, Finance and Governance CommitteeChief Executive Officer of Flagstone Re 2005 – 2012Chief Executive Officer, Centre Solutions 1994–1997Chairman of the Board of Bermuda Stock Exchange

Mark BarrenecheaCEO, CTO and board member of OpenTextBoard member of Dick’s Sporting GoodsFormerly president, CEO and board member of Silicon Graphics International Corporation; vice president, technology and business development of Tesseract Corporation; and senior vice president of applications development of OracleNamed Top New CEO of the Year by Canadian Business magazine in 2015Earned BSc in computer science from Saint Michael’s College in Vermont

Brian Duperreault – Chairman & CEO, Hamilton Insurance GroupForty year illustrious industry career includes serving as President & CEO, Marsh & McLennan Companies; non Executive Chairman of ACE Limited, and CEO and President of ACE Limited; various senior executive positions at American International Group (AIG)

Board positions include: Chairman of Attune, Chairman-elect of the Board of Directors of Blue Marble Microinsurance, International Insurance Society, and IESE Business School

Brad CooperSince 1990, Managing Partner and founding partner of Capital Z PartnersPrior to Capital Z, an investment banker in the Financial Institutions Group of Salomon Brothers

Board member of Make a Wish Foundation of Metro New York

Bill Freda – Chairman, Audit CommitteeRetired 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

Tom Hill – Chairman, Investment CommitteePresident and CEO of the Hedge Funds Solutions Group, a Vice Chairman of The Blackstone Group and Member of the Board of The Blackstone Group Management

Began career at First Boston, becoming one of the co-founders of its Mergers & Acquisitions Department

Board memberships include the Council on Foreign Relations and Lincoln Center Theatre

Russ Fradin Lead Independent Director of Best Buy Co., Inc., and Operating Partner of private equity firm Clayton, Dubilier & RiceFormerly 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 AssociatesHeld senior positions at Automatic Data Processing and McKinsey & CompanyEarned MBA from Harvard Business School and BSc in Economics and Finance from The Wharton School at the University of Pennsylvania

Joan Lamm-TennantChief Executive Officer of Blue Marble Microinsurance, an insurance industry collaborative announced in January 2015 to provide protection to the underservedPrior to Blue Marble, served as Global Chief Economist and Risk Strategist, Guy Carpenter & Company, LLCFaculty Member of the Wharton School, University of Pennsylvania

Steve PacalaFrederick D. Petrie Professor of Ecology and Evolutionary Biology at Princeton University; Director of the Princeton Environmental InstituteRecipient of the MacArthur Award, Mercer Award and the David Starr Jordan PrizeMember of the American Academy of Arts and Sciences and the National Academy of Sciences

John Overdeck – Chairman, Underwriting and Risk CommitteeCo-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 UniversityServes on the Boards of the Robin Hood Foundation, the Institute for Advanced Study and is the Vice Chair of the National Museum of Mathematics

Pauline RichardsCOO of Armour Group Holdings LimitedFormer 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

David Siegel – Chairman, 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

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Executive CommitteeBrian Duperreault – Chairman & CEO, Hamilton Insurance Group

Forty year illustrious industry career includes serving as President & CEO, Marsh & McLennan Companies; non Executive Chairman of ACE Limited, and CEO and President of ACE Limited; various senior executive positions at American International Group (AIG)

Board positions include: Chairman of Attune, Chairman-elect of the Board of Directors of Blue Marble Microinsurance, International Insurance Society, and IESE Business School

Jonathan Reiss – CFO

Member of the founding management team with 24 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

Seraina Macia – CEO, Hamilton USAFormerly held senior positions at AIG (CEO and EVP of Regional Management and Operations), AIG EMEA (CEO and President), XL Insurance North America (CEO), Zurich North America Commercial Specialties (President), Zurich Insurance Group (Head of Investor Relations) and NZB NeueZuercher Bank (Founding Partner)

Member of Board of Directors of Credit Suisse Group

Holds chartered Financial Analyst Designation

Victoria Guest – General Counsel

Member of the founding management team with 10 years’ experience in the insurance industry and 23 years of experience in corporate law

GC of Ariel Holdings (2009–2012)

GC of RAM Holdings (2006–2009)

Dermot O’Donohoe – CEO, Hamilton Underwriting Limited

Held various positions in Torus Group (now Starstone) including Transitional Group CEO and CEO Torus International (2009-2013)

18 years at XL Group in various positions, including Global Head of Specialty

Former member of Council of Lloyd’s (2007-2009); a Chartered Insurer (ACII)

Wendy Davis Johnson – Chief Communications Officer

Over 25 years’ experience in marketing communications and brand development

For the last 10 years, has been providing communications consulting services to corporate and non-profit organizations

Former SVP, Global Communications, ACE Group

Bob Deutsch – Chief Strategy Officer, Hamilton Insurance Group

35 year industry career includes founder and CEO of Ironshore Inc., EVP and CFO of CNA Financial Corporation, a founder of Executive Risk and President of its insurance subsidiaries as well as Chief Actuary and CFO

Fellow of the Casualty Actuarial Society

Current Board member of Wilton Re; past Board memberships include Beazley Furlong, Chaucer, Darwin, Enstar US and Platinum

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

CUO International of ACE Tempest Re (2005–2012)

Chair, Women in Reinsurance (Bermuda)

Pete Skerlj – Chief Risk Officer

Member of the founding management team with 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

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Insurance and Reinsurance Operations

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Established book of business in fifth year of growth; produced underwriting profit every year since inception

Shareholder’s equity over $1.5 billion as of December 31, 2016

Wrote over $250 million in 2016; forecast to write approximately $290 million in 2017

Maintains a conservative risk profile, limiting PML to 15% of shareholder’s equity in the US and 10% for the rest of the world

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.

Rated “A-” (Excellent) with a stable outlook by A.M. Best

Bermuda-based Class 4 property and casualty (re)insurer

Hamilton Re

OVERVIEW GROSS PREMIUMS WRITTEN(1)

Kathleen ReardonCEO, Hamilton Re

(1)Pie charts reflect in-force portfolio as of January 1, 2017

Property36.2%

Specialty26.8%

Professional Liability27%

Health Care4%

Multi-Line12%

Commercial Motor12%

Personal Motor6%

Excess/Umbrella

Liability25%

General Liability14%

Casualty37.1%

Worldwide10%

USA (Includes Caribbean)

66%

Financial Lines37%

Agriculture6%

Terror/PV3% Accident & Health

3%

WC/PA Cat3%

Multi-Line17%

Marine & Energy22%

Aviation & Space9%

Multi-Territory1%

Japan7%

Europe10%

Canada2%

Australasia4%

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Hamilton at Lloyd’s

OVERVIEW ACTUAL 2016 YOA GPW - $100 MILLION

PLANNED 2017 YOA GPW - $150 MILLION

Global licenses of Lloyd’s iconic brand

On April 1, 2015, Hamilton purchased a Lloyd’s Managing Agent, Sportscover Underwriting Limited (subsequently renamed Hamilton Underwriting Limited)

Hamilton Underwriting Limited currently manages Lloyd’s Syndicate 3334

Syndicate 3334 is marketed as Hamilton at Lloyd’s

Solvency II compliant, with no capital loadings applied

Approved by Lloyd’s to write $150m of premiums for the 2017 Year of Account ("YOA") and to add two lines of business in 2017 (Marine Liability and War & Terror)

Received approval from Lloyd’s in 2016 to acquire renewal rights for CNA Hardy’s A&H account

Credit ratings:

• A.M. Best: “A” (Excellent)

• S&P: “A+” (Strong)

• Fitch: “AA-” (Very Strong)

Dermot O’Donohoe CEO, Hamilton Underwriting Limited

Professional lines/Casualty22%

Property19%

Treaty Reinsurance24%

Space10%

Specialty25%

Professional lines/Casualty20%

Property14%

Treaty Reinsurance24%

Space8%

Specialty28%

Marine6%

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Hamilton USA

In partnership with Two Sigma, aims to deliver cutting-edge analytics and technology to agents and brokers resulting in improved transaction efficiency and underwriting results

Offers products to commercial lines customers with exceptional ease of submission and management for distribution partners.

In partnership with AIG and Two Sigma, launched Attune:

• A technology platform that accelerates the vision of using analytics and technology to improve efficiency, reduce costs and strengthen underwriting for small business in the US.

• Admitted business owners policies written in 1Q 2017

• AIG’s excess products for main street and specialty business to be introduced later in 2017

• Other lines of business including Workers Comp and Auto coming in 2018

Launched MyAttune, a mobile friendly platform that rates, quotes, binds and issues policies in a few minutes

Strategic review underway to expand Hamilton’s and Attune’s capabilities to adjacent Middle Market segment

Strategic decision made to transition from existing Programs business

Benefits from Hamilton’s A.M. Best Group Rating of “A-” and Financial Size Category of “XIV”

ACTUAL 2016 GPW - $105 MILLIONOVERVIEW

Seraina MaciaCEO, Hamilton USA

Property66%

Admitted BOP2%

Excess Liability2%

GL30%

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Attune is building a market leading, technology-based platform in the $120 billion Small to Medium Enterprise (SME) market

Initial book to represent approximately $300 million in premium

Represents an unprecedented partnership that leverages data science, technology, brand awareness and extensive claims data

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Will be synonymous with innovation, ease of use, speed, customer centricity and partnership.

Will meet the needs of a diverse customer base while maximizing cross-sell opportunities through AIG’s vast product offering and Hamilton USA’s underwriting methodology and user experience, creating a complete and efficient business insurance solution.

Will offer a fully streamlined, straight-through processing insurance buying experience for SMEs regardless of how they choose to purchase insurance, including new and emerging distribution partners.

Will use external data and scalable technology to eliminate the need to ask underwriting questions, remove human bias, prefill data, reduce frictional costs, increase transactional velocity, and target and retain more profitable business. Advanced analytics will improve risk selection, pricing efficacy, claims management and overall portfolio optimization.

BRAND

PRODUCT

DISTRIBUTION

DATA & TECHNOLOGY

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Two Sigma

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Deploy and seek to continuously improve intelligent investment management systems first created in 2001

Manage approximately $41.1 billion of assets for a global, diversified client base in absolute return and benchmark-relative investment mandates(2)

Trade equities, futures, FX, and derivatives in 70+ countries utilizing a highly diversified set of systematic strategies

Tap the talents of 1,100+ employees headquartered in New York with additional offices in Houston, London, and Hong Kong(2)

Operate as a Registered Investment Adviser with the SEC(3)

Computing Power & Data:

6,150+ servers in our computing environment, with 95,000 vCPUs and 1,695 terabytes of memory

35+petabytes of data and growing

10K+ data sources including public and proprietary

Human Capital

3,300 person years of R&D

Two thirds of staff consist of Engineers and Modelers

72% non-financial backgrounds

97% voluntary employee retention, since inception

Performance(4)

Created positive net alpha every year since inception (15 Years)

96% of investors have earned positive alpha

80% positive (net alpha) product quarters

WHAT WE DO

WHERE WE ARE TODAY

Two Sigma(1) 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.

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 February 1, 2015.(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) “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, 2016. 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).

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FINANCIAL HIGHLIGHTS CORPORATE ORGANIZATION CHART

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Appendix

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Hamilton Insurance Group Financial Highlights

CONSOLIDATED BALANCE SHEETS

December 31, 2016 December 31, 2015 December 31, 2014

($ in millions) Audited Audited Audited

Cash and investments $ 1,917 $ 1,819 $ 1,231

Premiums receivable 134 75 51

Losses and LAE recoverable 108 113 86

Intangible assets 39 41 7

Other 118 68 24

Total assets 2,316 2,116 1,399

Reserve for losses and LAE 336 226 147

Unearned premiums 209 97 51

Payable to related parties 27 158 117

Notes payable 20 20 15

Other 69 50 22

Total liabilities 661 551 352

Non-controlling interest — — —

Shareholders’ equity 1,655 1,565 1,047

Total liabilities and shareholders’ equity $ 2,316 $ 2,116 $ 1,399

Book value per share $ 16.22 $ 15.43 $ 12.83

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Hamilton Re Financial Highlights

CONSOLIDATED BALANCE SHEETS

December 31, 2016 December 31, 2015 December 31, 2014

($ in millions) Audited Audited Audited

Cash and investments $ 1,802 $ 1,746 $ 1,177

Premiums receivable 137 79 51

Losses and LAE recoverable 28 11 1

Other 88 56 24

Total assets 2,055 1,892 1,253

Reserve for losses and LAE 242 124 61

Unearned premiums 182 93 51

Payable to related parties 24 154 113

Notes payable 20 20 15

Other 26 16 44

Total liabilities 494 407 284

Non-controlling interest 8 3 2

Shareholder’s equity 1,553 1,482 967

Total liabilities and shareholder's equity $ 2,055 $ 1,892 $ 1,253

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Corporate Organization Chart

Hamilton Insurance Group, Ltd. (Bermuda)

September 4, 2013

Hamilton Insurance Services (Bermuda), Ltd.

Hamilton U.S. Holdings, Inc. (Delaware)

February 5, 2014

Hamilton Specialty Insurance Company

(Delaware)

(acquired October 6, 2014)

Hamilton Insurance Company (Delaware)

(acquired October 6, 2014)

Lloyd’s Syndicate 3334 (Managed by Hamilton Underwriting Limited)

Hamilton Services, LLC (Delaware)

February 5, 2014

Hamilton Underwriting Limited (U.K.)

(acquired April 1, 2015)

Hamilton Corporate Member Limited

(U.K.)

(acquired April 1, 2015)

Attune Holdings, LLC (Delaware)

August 15, 2016

Attune Insurance Services, LLC

(Delaware)

February 5, 2015

Hamilton Customer Care Insurance Services, LLC

(acquired April, 2016)

Hamilton Re, Ltd. (Bermuda)

June 8, 2012

Hamilton UK Holdings Limited (U.K.)

September 30, 2014

33.3%

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Wellesley House North, 1st Floor 90 Pitts Bay RoadPembroke HM08

Bermuda+1 (441) 405 5200

www.hamiltongroup.com

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