Skyward Specialty Insurance : SKWD Investor Presentation - May 2026
SKWD
Published on 05/12/2026 at 10:40 am EDT
May 2026
Corporate Scale
Ticker
SKWD (NASDAQ)
Market Capitalization1
$2.1 BILLION
Gross Written Premiums2
$2.7 BILLION
Managed Premiums3
$4 BILLION
Financial Strength & Stability
AM Best Rating
A (Excellent)
Book Value Per Share3
$27.50
Operating EPS Growth4
39%
Combined Ratio3
89.5%
Leadership Momentum
S&P 500 Named
#7 Top
Commercial Carrier
We are led by a deeply experienced and entrepreneurial leadership team, averaging more than 30 years in the industry
Market Capital ization is as of December 31, 2025
Gross Written Premiums and Managed Premiums are pro forma trailing twelve months as of March 31, 2026
Book Value Per Share and Combined Ratio as of March 31, 2026
Diluted operating earnings per share as of March 31, 2026 compared to March 31, 2025
4
Top Quartile Financial Performance
5
Unmatched Portfolio Diversification & Growth Engines
Differentiated "Rule Our NicheTM" Strategy
& Technology DNA
Highly Specialized & Innovation Leader
Conservative Balance Sheet
1
Top Quartile Financial Performance
OUR DUAL PLATFORM POWERS TOP QUARTILE RESULTS
Our combined US and Lloyd's platforms offer extensive reach, highly diversified portfolio
with capital flexibility, driving consistent top-quartile financial performance.
DIVERSIFIED US SPECIALTY
9 operating divisions of high-margin, hyper-niche domestic specialty segments
More than $2 billion in gross written premiums
60/40 premium mix in short tail (less than 2 years), medium tail (between 2-5 years) liabilities
LLOYD'S PLATFORM
Specialty Syndicate 1969 (diversified multi-class portfolio) & ibott1 (sharing economy/autonomy)
More than $1.5 billion
of managed premiums
3/4 of capital provided by third parties, resulting in significant fee income
(1) Syndicate 1971, our digital economy syndicate.
1
Top Quartile Financial Performance
TOP QUARTILE UNDERWRITING PERFORMANCE
We have consistently delivered top quartile underwriting profitability with low volatility since entering the public market in 2023.
Three Year Combined Ratio & Standard Deviation1
RLI
Kinsale
W.R. Berkley
MORE PROFITABLE, MORE VOLATILE
Skyward Group
MORE PROFITABLE, LESS VOLATILE
LESS PROFITABLE, MORE VOLATILE
LESS PROFITABLE, LESS VOLATILE
Old Republic
Arch
Hamilton
Markel
Bowhead
5.0%
4.0%
3.0%
2.0%
1.0%
0.0%
88.0%
89.0%
90.0%
91.0%
92.0%
93.0%
94.0%
95.0%
96.0%
97.0%
98.0%
Our average Net Combined Ratio was 90.8%(2)
as of December 31, 2025.
Axis - Insurance segment, excludes ~2% points of corporate
expenses not reflected in segment results
Arch - Insurance segment Hamilton - International segment Old Republic - Specialty segment
Net Combined Ratio Comparison based on public releases from 2023 to 2025
Average net combined ratio is the average of the Decembre 31, 2025 combined ratio and December 31, 2024 and 2023 adjusted com bined ratios. See Non-GAAP Re conciliations in the
December 31, 2024 10 -K.
1
Top Quartile Financial Performance
WITH YEAR OVER YEAR PREMIUMS & EARNINGS GROWTH
Gross Written Premiums1 ($ in millions) Operating Income2,3 ($ in millions)
52%
$2,644
$167
GROWTH
19%
GROWTH
27%
GROWTH
$1,743
$1,460
$1,144
32%
GROWTH
58%
GROWTH
$127
37%
GROWTH
$81
$59
2022 2023 2024 2025
2022 2023 2024 2025
The years ended December 31, 2022 through 2024 are Skyward Specialty and 2025 is pro forma Skyward Group.
The years ended December 31, 2022 through 2025 are reported Skyward Specialty.
The years ended December 31, 2022 through 2024 reflect adjusted operating income, see "Reconcliations of Non -GAAP Financials Measures" reported in the December 31, 2023 and 2024 10 -K.
1
Top Quartile Financial Performance
MEANINGFUL VALUE CREATION FOR INVESTORS
18.4% GROWTH
26%
GROWTH
GROWTH
$24.92
$27.50
$19.79
$16.72
CAGR = 41%
$1.17 $1.25
$1.05
$0.90 $0.89
$0.75 $0.80 $0.71 $0.80
$0.65 $0.61
$0.42 $0.42
Book Value Per Share1 Diluted Operating Earnings Per Share2
10.4%
1Q23 2Q23 3Q23 4Q23 1Q24 2Q24 3Q24 4Q24 1Q25 2Q25 3Q25 4Q25 1Q26
2023 2024 2025 1Q2026
Return On Equity1 Return on Tangible Equity
18.9%
15.9%
16.3%
2023 2024 2025
Book Value Per Share, Return on Equity and Return on Tangible Equity for the years ended 2023 - 2025 are reported Skyward Specialty.
20.9%
19.8%
17.9%
2023 2024 2025
The periods ended 2023 and 2024 reflect adjusted operating earnings per share, see "Reconcliations of Non -GAAP Financials Measures included in each respective period filing with the SEC.
2
Unmatched Portfolio Diversification & Growth Engines
UNDERWRITING PORTFOLIO UNLIKE ANY OTHER IN THE INDUSTRY
We operate across 11 distinct underwriting divisions, targeting niche markets where we can build a competitive moat.
Syndicate 1969
Accident & Health
Transactional E&S
ibott2
5%
7%
11%
GWP1
11%
12%
Global Agriculture
Credit & Surety 9%
$2.7 B
10%
The construction of our portfolio is intentionally balanced with our largest business representing only 13% of total GWP.
Nearly half3the portfolio is in low P&C cycle sensitive lines, we can outearn regardless of market backdrop.
Captives
Specialty Programs
13%
5% 6%
9%
Energy Solutions
Professional Lines
Global Property
Gross Written Premiums are pro forma TTM as of March 31, 2026.
Syndicate 1971, our digital economy syndicate.
47% of portfolio in less cycle-sensitive business lines including Accident & Health, Captives, Credit & Surety, Global Agriculture and ibott
2
Unmatched Portfolio Diversification & Growth Engines
FEE ENGINE MULTIPLIES PORTFOLIO VALUE
27%
MANAGED
PREMIUMS
Underwriting Premium 63%
$4.2B1
10%
Apollo-managed syndicates fully capitalized by
third-parties.
$0.42B
PARTNER SYNDICATES
Portion of Syndicate 1969 and ibott2 capitalized by third-parties
$1.12B
ALIGNED SYNDICATES
FEE PREMIUM
Fee-driving premiums adds $1.5B to the $2.7B in underwriting premiums.
Fee-driving premiums are capital-light, recurring and incremental to underwriting premiums.
Fee-driving premiums represent a structurally important growth lever as volumes scale over time.
Managed Premiums are pro forma TTM as of March 31, 2026.
Syndicate 1971, our digital economy syndicate.
3
Differentiated "Rule Our Niche" Strategy & Technology DNA
RULE OUR NICHE: HOW WE WIN IN THE MARKET
Our market leading underwriting strategy delivers superior risk-adjusted returns and durable enterprise value through lower volatility, scalable growth and a defensible competitive moat.
Targeted Niche Markets
We own narrowly defined, specialty segments and build defensible positions with lower volatility where standard
carriers fall short.
Elite, Empowered Talent
We attract and retain the industry's top professionals and empower them with the tools to perform at the highest level.
RULE OUR NICHE STRATEGY
Bespoke, Differentiated Solutions
We provide differentiated products, services and solutions tailored precisely to meet the unique needs of our target markets.
Advanced Tech & Data Analytics
Combine advanced analytics, proprietary
data, and automation to elevate risk selection, dynamic pricing, portfolio management.
12
3
Differentiated "Rule Our Niche" Strategy & Technology DNA
TALENT IS OUR PROPRIETARY ADVANTAGE
STRATEGIC ALIGNMENT & CULTURE
Culture Fuels the "Rule Our Niche" Strategy
PERFORMANCE & RETENTION METRICS
Talent model is focused on specialization, expertise, and execution to drive faster decision making and deeper underwriting discipline.
Performance Linked Compensation Compensation and incentives are directly tied to business outcomes to reinforce long-term value creation.
Geographic Talent Access
98% hybrid workforce enables access to top-tier global talent regardless of location.
<1%
Turnover in Business
Critical Roles
Exceptional stability in key positions
97%
Employee
Satisfaction
TURNOVER WORKFORCE COMPARISON
Overall Retention
Skyward Group
Industry
88%
80%
Voluntary Turnover
Skyward Group 4.2%
Industry
8.2%
High engagement supports culture of execution and growth
<60 days
Rapid Talent Acquisition
Speed to fill roles maintains operational scale
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
Chairman and CEO, Skyward Group
Mark Haushill
Chief Financial Officer,
Skyward Group
John Burkhart
President, US P&C, Skyward Specialty
David Ibeson
CEO, Apollo
Shakoor Kahn
Chief Strategy & Corporate
Dev., Skyward Group
Taryn McHarg
CFO, Apollo & Deputy CFO, Skyward Group
Patricia Ryan Chief Legal Officer, Skyward Group
Tom Schmitt
Chief People Officer, Skyward Group
James Slaughter Chief Underwriting Officer, Apollo
3
Differentiated "Rule Our Niche" Strategy & Technology DNA
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.
AMPLIFY OUR INSIGHT
Our continuously learning AI models provide real-time portfolio and performance insights that improve pricing, risk selection, and overall underwriting outcomes.
INGESTION
Our proprietary platform uses AI to rapidly process and structure submission data, automating intake and surfacing key insights before underwriter review.
40%
FASTER SUBMISSION DELIVERY
47%
TO UNDERWRITER
GWP IN 2025 WAS INFLUENCED BY
PREDICTIVE ANALYTICS
AGENTIC UNDERWRITING
AI-driven workflows streamline submissions with data-backed insights, allowing underwriters to focus on high-value decisions and outcomes
AUGMENTATION
We enhance underwriting decisions by integrating internal, third-party, and public data to deliver richer insights while keeping experts firmly in control.
80%
UNDERWRITTEN GWP
35%
POWERED BY AUGMENTED DATA
TIME TO QUOTE IMPROVEMENT
2
Differentiated "Rule Our Niche" Strategy & Technology DNA
OUR RULE OUR NICHE STRATEGY IN ACTION
We have established market leading positions through proprietary underwriting and specialized product
innovation. See the strategy in action through case studies of two industry leading divisions below.
SURETY IBOTT1,2
(SKYWARD SPECIALTY)
Grew from $12M at year-end 2020 to more than
$168M at year-end 2025
SCALE & PROFITABILITY
(APOLLO)
Launched in 2018 and grew to $510M by year-end 2025
Tailored solutions including small business administration, fiduciary and Judicial, transactional
BESPOKE SOLUTIONS
Highly specialized embedded platform liability and dynamic, usage-based products
Balanced portfolio comprising 55% contract
and 45% commercial bonds
NICHE MARKETS
Capitalizing on digital economy risk market; maintaining limited competition
Led by veteran Surety experts and backed by a dedicated team of more
than 60 underwriting specialists
ELITE TALENT
Unmatched expertise with dedicated specialists
focused specifically in digital risk and embedded data
Creation of industry first products, like EndWell Protection for complex energy decommissioning
MARKET INNOVATION
Launched a first-of-its-kind Autonomous Vehicle Insurance Program in partnership
with Marsh for Uber
Syndicate 1971, our digital economy syndicate.
Prof forma gross written premiums and fee generating managed premiums for the year-ended 2025.
4
Highly Specialized & Innovation Leader
Skyward Specialty is a recognized leader in tailoring solutions in the most niche markets creating solutions where traditional solutions fall short.
PARTNERED WITH
GRADIENT AI
Reimagining Medical
Stop Loss
ESTABLISHED DEALER
OPEN LOT CAPTIVE
Understory Weather to reimagine this class of business with data
analytics
DEVELOPED DAIRY LIVESTOCK SOLUTION
Designed to address unique and niche risks of dairy farming globally
LAUNCHED ENDWELL PROTECTION BONDS
First-of-its kind bond product for well decommissioning
EXPANDED LIFE SCIENCE SOLUTION GLOBALLY
Leveraging global markets
2022
Moved from SPA and created first and only syndicate focused on new economy opportunities
CREATED IBOTT SYNDICATE
1971
2023
In partnership with major global tech client this captive is the first in the
modern era
LAUNCHED FIRST LLOYD'S
CAPTIVE
2024
Added third party syndicate management capabilities, as additional fee income engine
INTRODUCED THIRD PARTY
SYNDICATE MANAGEMENT
2025
Innovation facility in partnership with Moonrock
LEAD ON NEW £75M DRONE, eVTOL
2026
through Lloyd's of London
licensing
INTRODUCED UBER AUTONOMOUS VEHICLE INSURANCE PROGRAM
First-of-its kind embedded
solution on Uber's platform
Apollo has an unrivaled track record of product innovation within
Lloyd's of London leveraging best-in-class augmented underwriting and technology capabilities.
5
Conservative Balance Sheet
CONSERVATIVE INVESTMENT PORTFOLIO
5.3%
FIXED INCOME
YIELD1
$2.7 B
TOTAL INVESTED
ASSETS
We are guided by key tenets of capital preservation and a balanced risk/reward approach. We continue to deploy free cashflow to our Fixed Income portfolio in line with our investment strategy.
Investment Portfolio as of March 31, 2026
Alternative & Strategic 6%
Short-Term 14%
3.5 Years
PORTFOLIO DURATION
"A+"
WEIGHTED AVERAGE
CREDIT QUALITY
Fixed Income 80%
5
Conservative Balance Sheet
We are committed to establishing and maintaining a strong balance sheet, starting with conservative loss reserves and strong capitalization ratios.
Overall Net Reserves1
26%
26%
38%
37%
31%
62%
63%
69%
74%
74%
100%
80%
Our reserve position is increasingly strong while simultaneously shortening the liability duration.
60%
40%
We believe this is imperative to maintain the confidence of customers, distribution partners, reinsurers, regulators, rating agencies and shareholders.
20%
0%
2022 2023 2024 2025 1Q 2026
(1) The years ended December 31, 2022 through 2025 are reported Skyward Specialty.
Top Quartile Financial Performance
5
Differentiated "Rule Our Niche" Strategy
& Technology DNA
Unmatched Portfolio Diversification & Growth Engines
Highly Specialized & Innovation Leader
Conservative Balance Sheet
Disclaimer
Skyward Specialty Insurance Group Inc. published this content on May 12, 2026, and is solely responsible for the information contained herein. Distributed via Public Technologies (PUBT), unedited and unaltered, on May 12, 2026 at 14:39 UTC.