Skyward Specialty Insurance Group, Inc. · NASDAQ:SKWD
Skyward Specialty Insurance — Merger or Acquisition (September 2025)
18 slides from Skyward Specialty Insurance's merger presentation, Sep 2, 2025
Slide 1: Skyward to Acquire Apollo Group Holdings: Amplifying Our "Rule Our Niche" Strategy
SKYWARD TO ACQUIRE APOLLO GROUP HOLDINGS: AMPLIFYING OUR “RULE OUR NICHE” STRATEGY SEPTEMBER 2, 2025
Slide 2: Disclaimer
DISCLAIMER Forward-Looking Statements Except for historical information, all other information in this news release consists of forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. The forward-looking statements are typically, but not always, identif
Slide 3: A Strategically Impactful and Financially Compelling Transaction
A STRATEGICALLY IMPACTFUL AND FINANCIALLY COMPELLING TRANSACTION has agreed to acquire (Apollo Group Holdings Limited) from Alchemy, management, employees and other strategic investors 3
Slide 4: Transaction Overview
A STRATEGICALLY IMPACTFUL AND FINANCIALLY COMPELLING TRANSACTION Transaction overview • Skyward has entered into a definitive agreement with the majority sellers to acquire 100% of Apollo Group Holdings (“Apollo”) for $555m • Represents <9x 2025E EBITDA • Expected to deliver double-digit adjusted op
Slide 5: A Strategically Impactful and Financially Compelling Transaction
A STRATEGICALLY IMPACTFUL AND FINANCIALLY COMPELLING TRANSACTION 1 Apollo is a high growth, low volatility, top quartile Lloyd’s specialty insurance platform with a unique proposition exceptionally well matched to Skyward 2 Adds over $1.5bn(1) of managed premium in attractive new niches, reinforcing
Slide 6: Apollo: A High Growth, Low Volatility, Top Quartile Specialty Insurance Platform
APOLLO: A HIGH GROWTH, LOW VOLATILITY, TOP QUARTILE SPECIALTY 1 INSURANCE PLATFORM Business Description Managed Premium Evolution ($m)(2) Apollo syndicates (1969+1971) Third-party syndicates • Leading capital-light, innovation-focused, 1,374 1,502 specialty insurance platform, operating at Lloyd’s 1
Slide 7: Apollo: Lloyd's Syndicate Performance
1 APOLLO: A HIGH GROWTH, LOW VOLATILITY, TOP QUARTILE SPECIALTY INSURANCE PLATFORM 2020-2024 CY(1) ( Lloyd’s Syndicate Performance Reinsurance % vs. Volatility (Weighted Standard Deviation of Annual Combined Ratios) Lloyd’s Average(2) 0% Lowest avg. combined ratio, least volatility 1% 1971 34% 2% 3%
Slide 8: Adds Over $1.5bn of Managed Premium in Attractive New, Specialty Niches
2 ADDS OVER $1.5BN OF MANAGED PREMIUM IN ATTRACTIVE NEW, SPECIALTY NICHES Skyward + Apollo Pro Forma Business Mix(1, 2) • Apollo syndicates (1969 and 1971) add over $1.3bn(1) of managed Client Domicile premium, further strengthening Skyward’s position as a leading UK, 5% US-focused specialty insurer
Slide 9: Accelerates Innovation
3 ACCELERATES INNOVATION Apollo has an unrivalled track record of innovation within Lloyd’s of London • Launches innovative smart follow • In partnership with a major global tech • Lead on new £75m drone, • Launches ibott SPA focused on proposition (data enabled, semi-autonomous client, launches the
Slide 10: Accelerates Innovation (Cont'd)
3 ACCELERATES INNOVATION (CONT’D) ibott is the only insurer exclusively focused on new economy risks Syndicate 1971 / ibott has grown rapidly ibott overview GWP, $m 411 • Provides platform liability cover (typically the first excess 299 261 layer) for businesses operating in the new economy, 159 inc
Slide 11: Brings Predictable Fee-Based Earnings and Third-Party Capital Support
4 BRINGS PREDICTABLE FEE-BASED EARNINGS AND THIRD-PARTY CAPITAL SUPPORT Underwriting / Fee Income Split(1,2) 2025 Apollo Syndicate Capacity Providers(4) Underwriting Income 40% Fee-based Income 60%(3) 27% Fee income is comprised of managing agency fees (tied to premium) and profit commissions (tied
Slide 12: Leading Management Team and Strong Strategic / Cultural Alignment
5 LEADING MANAGEMENT TEAM AND STRONG STRATEGIC / CULTURAL ALIGNMENT Entrepreneurial and dynamic team, led by CEO David Ibeson, who has been with the business for more than a decade. Strong cultural alignment between Skyward and Apollo Senior leadership Underwriting leadership Strong cultural alignme
Slide 13: Highly Accretive Transaction, with Significant Incremental Value Creation Potential
6 HIGHLY ACCRETIVE TRANSACTION, WITH SIGNFICANT INCREMENTAL VALUE CREATION POTENTIAL Attractive valuation… … with multiple levers for significant additional value creation <9x Create an ibott US platform Apollo 2025E EBITDA Utilize Lloyd’s license network to serve US clients’ international needs | E
Slide 14: Skyward Team Has a Proven Track Record and the Experience to Deliver a Successful Combination
SKYWARD TEAM HAS A PROVEN TRACK RECORD AND THE EXPERIENCE TO DELIVER A SUCCESSFUL COMBINATION Proven track record of outperformance… …and relevant M&A / operational experience Skyward has underwritten at a profitable combined ratio since its listing… • The Skyward team has directly overseen the succ
Slide 15: A Strategically Impactful and Financially Compelling Transaction
A STRATEGICALLY IMPACTFUL AND FINANCIALLY COMPELLING TRANSACTION 1 Apollo is a high growth, low volatility, top quartile Lloyd’s specialty insurance platform with a unique proposition exceptionally well matched to Skyward 2 Adds over $1.5bn(1) of managed premium in attractive new niches, reinforcing
Slide 16: Q&A
Q&A 16
Slide 17: Appendix
APPENDIX
Slide 18: Apollo Financial Highlights
APOLLO FINANCIAL HIGHLIGHTS Apollo Group Standalone Key Financial Highlights (4) Figures in $m unless otherwise stated 2025E 2024 2023 (1) Managed Premium ($bn) 2.0 1.4 1.0 (2) EBITDA 65 60 38 Underwriting Income 22 17 15 Fee-based Income 27 26 14 Investment Income 13 15 8 Profit before Tax 63 59 37
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