HAMILTON INSURANCE

GROUPAPRIL 2016

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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.

our founding chairman, sandy weill, played a pivotal role in hamilton’s development from 2014 to 2016, and

remains a shareholder of hamilton to this day.

as of december 31, 2015, hamilton has over $1.5 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

president and ceo of marsh & mclennan companies until december 2012

ceo of ace limited from 1994 to 2004

nearly 20 years in various senior executive positions with aig

lead director of tyco’s Board of directors

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 approximately $31 billion

generated positive alpha and net returns every year since inception—13 consecutive years

leverages a diverse, experienced team of more than 900 employees, including 525+ modelers and engineers holding more than 130 phds

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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Bermuda-based class 4

property and casualty

(re)insurer

established book of business

in fifth year of growth

shareholder’s equity over $1.4

billion at december 31, 2015

wrote $206 million of gross

premiums in 2015;

forecast to write

$250 million in 2016

rated “a-” (excellent) with a

stable outlook by a.m. Best

hamilton at a glance

global licenses and imprimatur

of lloyd’s iconic brand

hamilton underwriting limited,

a lloyd’s managing agency,

controls syndicate 3334

approved by lloyd’s to write

over $100 million of premiums

for the 2016 Year of account

Benefits from lloyd’s ratings

from a.m. Best “a” (excellent);

s&p “a+” (strong); and fitch

“aa-” (very strong)

operations based in princeton,

new Jersey

• hamilton insurance company (delaware – admitted)

• hamilton specialty insurance company (delaware – e&s)

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

planned gross premiums written

for 2016 is approximately $110

million

Benefits from hamilton’s a.m.

Best group rating of “a-” and

financial size category of “xiii”

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

partnership with hamilton

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hamilton’s growth in Bv and se

book VALue PeR shARe ConsoLIdAted shARehoLdeRs’ equIty

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

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Board of directors and executive committee

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industry-renowned leadership

boARd of dIReCtoRs

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

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

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

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 Blue marble microinsurance, international insurance society, and iese Business school; lead director, tyco international

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

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

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

Bob Deutsch – Acting CEO, Hamilton USA; Chief Strategy Officer, Hamilton Insurance Group

thirty 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

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 Blackstone group managementBegan career at first Boston, becoming one of the co-founders of its mergers & acquisitions departmentBoard memberships include the council on foreign relations and lincoln center theatre

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 Blue marble microinsurance, international insurance society, and iese Business school; lead director, tyco international

Wendy Davis Johnson – Chief Communications

Officerover 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

Victoria Guest – General Counselmember of the founding management team; has 10 years of experience in the insurance industry and 22 years of experience in corporate law

gc of ram holdings (2006–2009)

gc of ariel holdings (2009–2012)

Jonathan Reiss – CFOmember of the founding management team and has more than 22 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

Dermot O’Donohoe – CEO, Hamilton Underwriting

Limitedmost recently held the position of group ceo of global specialty insurer torus group, where he oversaw the successful transition of torus’ ownership to Bermuda-based enstar in 2014

ceo of torus international (2009–2013)

14 years at xl group in various positions, including global head of specialty

former member of council of lloyd’s (2007–2009)

Bob Deutsch – Acting CEO, Hamilton USA; Chief Strategy Officer, Hamilton Insurance Group

thirty 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

Pete Skerlj – Chief Risk Officermember 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

Kathleen Reardon – CEO, Hamilton Remember of the founding management team and has 20 years of insurance industry experience

fellow of the casualty actuarial society

cuo international of ace tempest re (2005–2012)

chair, women in reinsurance (Bermuda)

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insurance and reinsurance operations

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

established book of business in fifth year of growth

shareholder’s equity over $1.4 billion as of december 31, 2015

wrote $206 million of gross premiums in 2015; forecast to write $250 million in 2016

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 as well as a proprietary risk management platform

generates strong risk-adjusted returns while maintaining liquidity to support underwriting operations

rated “a-” (excellent) with a stable outlook by a.m. Best

hamilton re was honoured in 2015 as “Bermuda reinsurer of the Year” by reactions magazine

hamilton re

oVeRVIeW gRoss PReMIuMs WRItten(1)

Kathleen ReardonCeo, hamilton Re

(1)pie charts reflect in-force portfolio as of January 1, 2016

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hamilton at lloyd’s

oVeRVIeW PLAnned 2016 gPW foR LLoyd’s

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

all senior underwriting and functional personnel now recruited

functions with a full Board and committee structure, including three independent directors

achieved solvency ii readiness ahead of 2016 go-live requirement

approved by lloyd’s to write over $100 million of premiums for the 2016 Year of account

credit ratings:

• a.m. Best: “a” (excellent)

• s&p: “a+” (strong)

• fitch: “aa-” (very strong)

Dermot O’Donohoe Ceo, hamilton underwriting Limited

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operations based in princeton, new Jersey

• hamilton insurance company (delaware – admitted)

licensed in 49 states and the district of columbia

• hamilton specialty insurance company (delaware – e&s)

eligible surplus lines insurer in 49 states and the district of

columbia

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. Business segments: small Business, middle markets and programs

planned gross premiums written for 2016 is approximately $110 million

execution of No hands touch the trade

• straight-through processing

• predictive analytics

• partnership with two sigma

Benefits from hamilton’s a.m. Best group rating of “a-” and financial size category of “xiii”

hamilton usa

oVeRVIeW 2016 PReMIuM estIMAtes

Producer Rank Premium Split1 31.8%2 22.7%3 7.3%4 6.4%5 4.6%6 3.6%7 3.6%8 3.6%9 2.7%10 2.7%other 11.0%

Total 100%

Bob DeutschActing Ceo, hamilton usA

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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 $31 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 40+ countries utilizing a highly diversified set of systematic strategies

tap the talents of 900+ 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:

4,500+ servers in our computing environment, with 87,000 vcpus and 1,000 terabytes of memory

22+petabytes of data and growing

10K+ data sources including public and proprietary

Human Capital

2600+ person years of r&d

2/3rds of staff consist of engineers and modelers

60% non-financial backgrounds

97% voluntary employee retention, since inception

Performance(4)

created positive net alpha every year since our inception (13 Years)

99% of our investors have earned positive alpha

85% 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, llc, and two sigma advisers, llc and their affiliates.(2) aum and employee count are approximate as of october 1, 2015.(3) two sigma investments, llc and two sigma advisers, llc 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, 2014. performance statistics only include performance of unaffiliated investors. “net product quarters” is an asset weighted figure derived by (i) adding the sum of the average notional aum of each two sigma-managed product group by quarter and (ii) dividing the number of positive net alpha quarters by the total number of product quarters.

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FINANCIAL HIGHLIGHTS CORPORATE ORGANIzATION CHART

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appendix

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hamilton insurance group financial highlights

($ in millions) December 31, 2015 December 31, 2014

cash and investments $ 1,819 $ 1,231

premiums receivable 75 51

losses and lae recoverable 113 86

intangible assets 41 7

other 68 24

Total assets 2,116 1,399

reserve for losses and lae 226 147

unearned premiums 97 51

payable to related parties 158 117

notes payable 20 15

other 50 22

total liabilities 551 352

non-controlling interest — —

shareholders’ equity 1,565 1,047

Total liabilities, non-controlling interest and shareholders’ equity $ 2,116 $ 1,399

Book value per share $ 15.43 $ 12.83

ConsoLIdAted bALAnCe sheets

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hamilton re financial highlights

($ in millions) December 31, 2015 December 31, 2014

cash and investments $ 1,746 $ 1,177

premiums receivable 79 51

losses and lae recoverable 11 1

other 56 24

Total assets 1,892 1,253

reserve for losses and lae 124 61

unearned premiums 93 51

payable to related parties 154 113

notes payable 20 15

other 16 44

total liabilities 407 284

non-controlling interest 3 2

shareholder’s equity 1,482 967

Total liabilities, non-controlling interest and shareholder's equity $ 1,892 $ 1,253

ConsoLIdAted bALAnCe sheets

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corporate organization chart

Hamilton Insurance Group, Ltd. (Bermuda)

september 4, 2013

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

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)

Kinetic Insurance Brokers Limited (U.K.)

(acquired april 1, 2015)

NHT3 Insurance Services, LLC (Delaware)

february 5, 2015

Hamilton Re, Ltd. (Bermuda)

July 8, 2012

Hamilton UK Holdings Limited (U.K.)

september 30, 2014

*as of april 2016

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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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