Skyward Specialty Insurance Group, Inc. · NASDAQ:SKWD
Skyward Specialty Insurance — Investor Presentation (August 2026)
24 slides from Skyward Specialty Insurance's investor presentation, Aug 10, 2026
Slide 1: Investor Presentation August 2026
INVESTOR PRESENTATION August 2026 Updated 8/10/2026
Slide 2: Disclaimer
DISCLAIMER Forward-Looking Statements This presentation may contain forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. The words “believe,” “may,” “will,” “intend,” “expect,” “anticipate,” “estimate,” “target,” and similar expressions, or the negat
Slide 3: Reimagining insurance to create greater resilience in an increasingly risky world
We are reimagining insurance to create greater resilience in an increasingly risky world.
Slide 4: Skyward Group Snapshot
SKYWARD GROUP SNAPSHOT Corporate Scale Financial Strength & Stability Leadership Momentum Ticker AM Best Rating S&P 500 Named SKWD (NASDAQ) A (Excellent) #7 Top Market Capitalization1 Book Value Per Share3 Commercial $2.4 BILLION $28.55 Carrier Gross Written Premiums2 Operating EPS Growth4 $2.7 BILL
Slide 5: We Are a Specialty Carrier Unlike Any Other
1 Top Quartile Financial Performance 2 Unmatched Portfolio Diversification & Growth Engines WE ARE A SPECIALTY 3 Differentiated “Rule Our NicheTM” Strategy CARRIER UNLIKE & Technology DNA ANY OTHER 4 Highly Specialized & Innovation Leader 5 Conservative Balance Sheet
Slide 6: Our Dual Platform Powers Top Quartile Results
1 Top Quartile Financial Performance OUR DUAL PLATFORM POWERS TOP QUARTILE RESULTS Our combined US and Lloyd’s platforms offer extensive reach, a highly diversified portfolio, capital flexibility, and consistent top-quartile financial performance. DIVERSIFIED US SPECIALTY LLOYD’S PLATFORM Specialty
Slide 7: Top Quartile Underwriting Performance
1 Top Quartile Financial Performance TOP QUARTILE UNDERWRITING PERFORMANCE Three Year Combined Ratio & Standard Deviation1 88.0% RLI Axis Kinsale 89.0% 90.0% W.R. Berkley Skyward AFG Ategrity 91.0% MORE PROFITABLE, MORE VOLATILE MORE PROFITABLE, LESS VOLATILE We have consistently delivered top quart
Slide 8: Meaningful Growth & Value Creation for Investors
1 Top Quartile Financial Performance MEANINGFUL GROWTH & VALUE CREATION FOR INVESTORS Gross Written Premiums ($ in millions) Diluted Operating Earnings Per Share2 CAGR = 38% $1.30 $2,166 $1.25 $1.17 $1,743 $1.05 $1,460 $0.90 $0.89 $0.80 $0.80 $1,144 $0.75 $0.71 $0.65 $0.61 $0.42 $0.42 2022 2023 2024
Slide 9: Underwriting Portfolio Unlike Any Other
2 Unmatched Portfolio Diversification & Growth Engines UNDERWRITING PORTFOLIO UNLIKE ANY OTHER Syndicate 1969 Accident & Health ibott2 9% 12% We operate across 11 distinct underwriting 6% divisions, targeting niche markets where we can Global Agriculture build a competitive moat. llo Transactional E
Slide 10: Fee Engine and Capital Flexibility Multiplies Portfolio Value
2 Unmatched Portfolio Diversification & Growth Engines FEE ENGINE AND CAPITAL FLEXIBILITY MULTIPLIES PORTFOLIO VALUE Fee-driving premiums adds $1.6B to the $2.7B in underwriting premiums, FEE PREMIUM resulting in $4.3B in ALIGNED SYNDICATES managed premiums. 26% $1.1B Portion of Syndicate 1969 and i
Slide 11: Rule Our Niche: How We Win in the Market
3 Differentiated “Rule Our Niche” Strategy & Technology DNA RULE OUR NICHE: HOW WE WIN IN THE MARKET Our market leading underwriting strategy is founded in building defensible competitive moats to deliver sustainable superior risk-adjusted returns and durable growth in shareholder value. Targeted Ni
Slide 12: Talent Is Our Proprietary Advantage
3 Differentiated “Rule Our Niche” Strategy & Technology DNA TALENT IS OUR PROPRIETARY ADVANTAGE STRATEGIC ALIGNMENT & CULTURE PERFORMANCE & RETENTION METRICS Culture Fuels the “Rule Our Niche” Strategy Talent model is focused on specialization, expertise, <1% 97% <60 days and execution to drive fast
Slide 13: Skyward Group Executive Leaders
3 Differentiated “Rule Our Niche” Strategy & Technology DNA SKYWARD GROUP EXECUTIVE LEADERS We are led by an entrepreneurial executive management team with decades of insurance leadership experience spanning multiple aspects of the global P&C industry. Andrew Robinson Mark Haushill John Burkhart Dav
Slide 14: Our Technology DNA: Bionic Underwriting
3 Differentiated “Rule Our Niche” Strategy & Technology DNA OUR TECHNOLOGY DNA: BIONIC UNDERWRITING Skyward Specialty’s bionic underwriting uses expert judgment with AI-driven insights and automation to remove constraints and deliver faster, more precise and consistent decisions at scale. 40% FASTER
Slide 15: Our Rule Our Niche Strategy in Action
3 Differentiated “Rule Our Niche” Strategy & Technology DNA OUR RULE OUR NICHE STRATEGY IN ACTION SURETY IBOTT1,2 (SKYWARD SPECIALTY) (APOLLO) Grew from $12M at year-end 2020 to more than Launched in 2018 and grew to $510M by year-end $168M at year-end 2025, 17% net loss ratio3 SCALE & PROFITABILITY
Slide 16: Innovating in Niche Markets
4 Highly Specialized & Innovation Leader INNOVATING IN NICHE MARKETS Skyward Specialty is a recognized leader in tailoring solutions in the most niche markets creating solutions where traditional solutions fall short. PARTNERED WITH ESTABLISHED DEALER DEVELOPED DAIRY LAUNCHED ENDWELL GRADIENT AI OPE
Slide 17: Thoughtful Capital Managers
5 Conservative Balance Sheet THOUGHTFUL CAPITAL MANAGERS • Portfolio diversification provides allocation Current & Target Leverage of capital to support growth and maximize returns 35% 33% • Management is committed to thoughtful 30% returning any excess capital 26% 25% • In 2Q 2026, repurchased $10
Slide 18: Conservative Investment Portfolio
5 Conservative Balance Sheet CONSERVATIVE INVESTMENT PORTFOLIO Investment Portfolio as of June 30, 2026 We are guided by key tenets of capital preservation and a balanced risk/reward approach. We continue to deploy free Alternative cashflow to our Fixed Income portfolio in line with our & Strategic
Slide 19: Strong Reserve Position
5 Conservative Balance Sheet STRONG RESERVE POSITION Overall Net Reserves1 We are committed to establishing and maintaining a strong balance 100% sheet, starting with conservative loss reserves and strong 26% 26% 23% 31% capitalization ratios.. 80% 38% 37% Our reserve position is 60% increasingly st
Slide 20: We Are a Specialty Carrier Unlike Any Other
1 Top Quartile Financial Performance 2 Differentiated “Rule Our Niche” Strategy & Technology DNA WE ARE A SPECIALTY 3 Unmatched Portfolio Diversification CARRIER UNLIKE & Growth Engines ANY OTHER 4 Highly Specialized & Innovation Leader 5 Conservative Balance Sheet
Slide 21: Appendix
SKYWARD GROUP APPENDIX
Slide 22: Balance Sheet
BALANCE SHEET ($ in thousands) June 30, 2026 December 31, 2025 Assets Total cash and invested assets $ 3,040,911 $ 2,499,628 Funds at Lloyd’s 121,630 2,509 Options, at fair value 40,535 34,857 Premiums and commissions receivable, net 978,409 544,217 Reinsurance recoverables, net 1,411,648 1,119,880
Slide 23: Income Statement
INCOME STATEMENT ($ in thousands) Three months ended June 30, Six months ended June 30, 2026 2025 2026 2025 Revenues: Net earned premiums $444,472 295,542 $878,479 595,908 Underwriting fee income 12,588 - 22,666 - Commission and fee income 2,334 2,560 3,861 4,536 Net investment income 30,727 18,704
Slide 24: Gross Written Premiums & Managed Premiums
GROSS WRITTEN PREMIUMS & MANAGED PREMIUMS ($ in thousands) 1Q 2025 2Q 2025 3Q 2025 4Q 2025 1Q 2026 2Q 2026 Skyward Specialty Insurance Accident & Health $63,169 $60,489 $63,147 $67,298 $92,009 $95,456 Captives 66,929 76,995 67,955 62,376 57,914 64,251 Credit & Surety 45,027 55,132 52,785 61,503 64,1
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