Tearsheet

Skyward Specialty Insurance (SKWD)


Market Price (12/27/2025): $51.885 | Market Cap: $2.1 Bil
Sector: Financials | Industry: Property & Casualty Insurance

Skyward Specialty Insurance (SKWD)


Market Price (12/27/2025): $51.885
Market Cap: $2.1 Bil
Sector: Financials
Industry: Property & Casualty Insurance

Investment Highlights Why It Matters Detailed financial logic regarding cash flow yields vs trend-riding momentum.


0 Attractive yield
Total YieldTotal Yield = Earnings Yield + Dividend Yield, Earnings Yield = Net Income / Market Cap Dividend Yield = Total Dividends / Market Cap is 6.7%, FCF Yield is 18%
Key risks
SKWD key risks include [1] the challenge of accurately pricing unique, Show more.
1 Cash is significant % of market cap
Net D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is -65%
 
2 Strong revenue growth
Rev Chg LTMRevenue Change % Last Twelve Months (LTM) is 23%
 
3 Attractive cash flow generation
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 28%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 28%
 
4 Low stock price volatility
Vol 12M is 36%
 
5 Megatrend and thematic drivers
Megatrends include Cybersecurity, Fintech & Digital Payments, and Energy Transition & Decarbonization. Themes include Cloud Security, Show more.
 
0 Attractive yield
Total YieldTotal Yield = Earnings Yield + Dividend Yield, Earnings Yield = Net Income / Market Cap Dividend Yield = Total Dividends / Market Cap is 6.7%, FCF Yield is 18%
1 Cash is significant % of market cap
Net D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is -65%
2 Strong revenue growth
Rev Chg LTMRevenue Change % Last Twelve Months (LTM) is 23%
3 Attractive cash flow generation
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 28%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 28%
4 Low stock price volatility
Vol 12M is 36%
5 Megatrend and thematic drivers
Megatrends include Cybersecurity, Fintech & Digital Payments, and Energy Transition & Decarbonization. Themes include Cloud Security, Show more.
6 Key risks
SKWD key risks include [1] the challenge of accurately pricing unique, Show more.

Valuation, Metrics & Events

SKWD Stock


Why The Stock Moved


Qualitative Assessment

AI Analysis | Feedback

The requested time period for Skyward Specialty Insurance (SKWD) from August 31, 2025, to December 27, 2025, is in the future. As such, there is no historical stock movement data available to explain a 7.3% change within this specific future timeframe. However, recent news and analyst activity for SKWD up to the current date provide insights into factors influencing its stock performance in late 2025.

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<b>1. Regulatory Approvals for Apollo Group Holdings Acquisition:</b> Skyward Specialty Insurance received necessary regulatory and shareholder approvals for its acquisition of Apollo Group Holdings Limited, an announcement made on December 3, 2025. This news led to the stock gaining more than 5% since its release. The transaction is expected to close early in the first quarter of 2026.

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<b>2. Strong Financial Guidance for 2026:</b> Alongside the acquisition approval, Skyward Specialty provided strong financial guidance for the 2026 fiscal year. The company projected gross written premiums between $2.65 billion and $2.8 billion and net income ranging from $207 million to $216 million. Analysts noted that adjusted EPS guidance of $4.80 to $5.00 per share topped Wall Street estimates by 8%.

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<b>3. Analyst Rating Upgrades and Price Target Increases:</b> Following these developments, several analysts maintained or upgraded their ratings and increased price targets for SKWD. For example, a Citizens JMP analyst maintained a Buy rating and increased the price target to $80 from $75 per share on December 4, 2025. On December 5, a KBW analyst raised the firm's price target from $64 to $66, maintaining a Buy rating. William Blair also reiterated a Buy rating on December 9. The consensus analyst rating for SKWD is "Buy," with an average price target of $65.3, forecasting a 25.94% increase over the next year.

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<b>4. Third Quarter 2025 Results Exceeded Expectations:</b> Skyward Specialty Insurance reported exceptional third-quarter results for 2025, with revenues of $382.5 million, up 27.1% year-on-year, exceeding analysts' expectations by 14.3%. The company achieved a combined ratio of 89.2% and an annualized return on equity of 19.3%. Net premiums written increased by 64.4% to $441.2 million, surpassing expectations.

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<b>5. Strategic Growth and Diversification through Acquisition:</b> The acquisition of Apollo Group Holdings Limited is viewed as providing Skyward with a strong source of inorganic growth and diversification into the Lloyd's market, opening up new specialty business areas. This strategic move is expected to deliver double-digit adjusted operating earnings per share (EPS) accretion in the first full year after closing and add over $1.5 billion in managed premium.

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Stock Movement Drivers

Fundamental Drivers

The 10.3% change in SKWD stock from 9/26/2025 to 12/26/2025 was primarily driven by a 6.4% change in the company's Total Revenues ($ Mil).
926202512262025Change
Stock Price ($)47.0251.8510.27%
Change Contribution ByLTMLTM
Total Revenues ($ Mil)1257.821337.976.37%
Net Income Margin (%)10.49%10.55%0.59%
P/E Multiple14.4114.873.17%
Shares Outstanding (Mil)40.4540.49-0.10%
Cumulative Contribution10.27%

LTM = Last Twelve Months as of date shown

Market Drivers

9/26/2025 to 12/26/2025
ReturnCorrelation
SKWD10.3% 
Market (SPY)4.3%19.0%
Sector (XLF)3.3%49.6%

Fundamental Drivers

The -8.9% change in SKWD stock from 6/27/2025 to 12/26/2025 was primarily driven by a -19.4% change in the company's P/E Multiple.
627202512262025Change
Stock Price ($)56.9351.85-8.92%
Change Contribution ByLTMLTM
Total Revenues ($ Mil)1214.321337.9710.18%
Net Income Margin (%)10.22%10.55%3.27%
P/E Multiple18.4414.87-19.38%
Shares Outstanding (Mil)40.2040.49-0.72%
Cumulative Contribution-8.93%

LTM = Last Twelve Months as of date shown

Market Drivers

6/27/2025 to 12/26/2025
ReturnCorrelation
SKWD-8.9% 
Market (SPY)12.6%16.9%
Sector (XLF)7.4%40.5%

Fundamental Drivers

The 0.8% change in SKWD stock from 12/26/2024 to 12/26/2025 was primarily driven by a 22.5% change in the company's Total Revenues ($ Mil).
1226202412262025Change
Stock Price ($)51.4451.850.80%
Change Contribution ByLTMLTM
Total Revenues ($ Mil)1092.161337.9722.51%
Net Income Margin (%)12.24%10.55%-13.78%
P/E Multiple15.4314.87-3.64%
Shares Outstanding (Mil)40.1040.49-0.97%
Cumulative Contribution0.79%

LTM = Last Twelve Months as of date shown

Market Drivers

12/26/2024 to 12/26/2025
ReturnCorrelation
SKWD0.8% 
Market (SPY)15.8%30.8%
Sector (XLF)14.4%49.2%

Fundamental Drivers

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Market Drivers

12/27/2023 to 12/26/2025
ReturnCorrelation
SKWD52.0% 
Market (SPY)48.0%29.7%
Sector (XLF)51.8%47.7%

Return vs. Risk


Price Returns Compared

 202020212022202320242025Total [1]
Returns
SKWD Return---77%49%2%171%
Peers Return16%38%-12%21%26%16%150%
S&P 500 Return16%27%-19%24%23%18%114%

Monthly Win Rates [3]
SKWD Win Rate---75%58%50% 
Peers Win Rate52%65%42%68%57%52% 
S&P 500 Win Rate58%75%42%67%75%73% 

Max Drawdowns [4]
SKWD Max Drawdown----6%-12%-17% 
Peers Max Drawdown-34%-5%-26%-7%-9%-23% 
S&P 500 Max Drawdown-31%-1%-25%-1%-2%-15% 


[1] Cumulative total returns since the beginning of 2020
[2] Peers: HPQ, HPE, IBM, CSCO, AAPL.
[3] Win Rate = % of calendar months in which monthly returns were positive
[4] Max drawdown represents maximum peak-to-trough decline within a year
[5] 2025 data is for the year up to 12/26/2025 (YTD)

How Low Can It Go

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In The Past

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About Skyward Specialty Insurance (SKWD)

We are a growing specialty insurance company delivering commercial property and casualty (“P&C”) products and solutions on a non-admitted (or excess and surplus (“E&S”)) and admitted basis, predominantly in the United States. We focus our business on markets that are underserved, dislocated and/or for which standard insurance coverages are insufficient or inadequate to meet the needs of businesses, including our customers and prospective customers operating in these markets. Our customers typically require highly specialized, customized underwriting solutions and claims capabilities. As such, we develop and deliver tailored insurance products and services to address each of the niche markets we serve. Our portfolio of insured risks is highly diversified — we insure customers operating in a wide variety of industries; we distribute through multiple channels; we write multiple lines of business, including general liability, excess liability, professional liability, commercial auto, group accident and health, property, surety and workers’ compensation; we insure both short and medium duration liabilities; and our business mix is balanced between E&S and admitted markets. All of these factors enable us to respond to market opportunities and dislocations by deploying capital where we believe we can consistently earn attractive risk-adjusted returns. We believe this diversification, combined with our underwriting and claims expertise, will produce strong growth and consistent profitability across P&C insurance pricing cycles. We seek to lead in our chosen market niches and establish sustainable competitive positions in these markets. The following key elements underpin our strategy and approach to our business: 1. Providing differentiated products, services and solutions that meet the unique needs of our target markets; 2. Attracting and retaining exceptional underwriting and claims talent and incentivizing our professionals in a manner that aligns with our organization and corporate goals; 3. Amplifying the expertise of our people with advanced technology and analytics that enable superior risk selection, pricing and claims management; 4. Empowering our underwriting and claims teams with considerable authority to make decisions and apply their expertise; and 5. Fostering a culture that promotes nimbleness and responsiveness to market opportunities and dislocation. We refer to this strategy as “Rule Our Niche” and it forms the basis of our approach to building a strong defensible market position, creating a competitive moat, and winning in our chosen markets. We believe that the principles underlying our strategy are key to achieving and sustaining best-in-class underwriting results through P&C insurance pricing cycles. We consistently strive for excellence in risk selection, pricing, and claims outcomes, and to amplify these critical functions with the use of advanced technology and analytics. We are led by an entrepreneurial executive management team with decades of insurance leadership experience spanning multiple aspects of the global P&C industry. Our leadership is supported by an experienced team with a broad skillset and aligned around our strategy. We believe our high-quality leadership and underwriting and claims teams, technology DNA, advanced analytics capabilities, diversified book of business, and strong competitive position in each of our chosen market niches position us to continue to profitably grow our business. We aim to deliver long-term value for our shareholders by generating best-in-class underwriting profitability and book value per share growth across P&C market cycles. For the nine months ended September 30, 2022, we wrote $879.1 million in gross written premiums and had a combined ratio of 94.7% and an adjusted combined ratio of 92.6%. At September 30, 2022, our stockholders’ equity was $399.8 million. For the nine months ended September 30, 2022, we generated $19.0 million and $46.9 million of net income and adjusted operating income, respectively, a 6.1% and 15.2% annualized return on equity and annualized adjusted return on equity, respectively and a 7.9% and 19.4% annualized return on tangible equity and annualized adjusted return on tangible equity, respectively. For the year ended December 31, 2021, we wrote $939.9 million in gross written premiums, had a combined ratio of 97.8% and an adjusted combined ratio of 94.6%, and our stockholders’ equity was $426.1 million at year end, an increase of 8.3% compared to the prior year period. For the year ended December 31, 2021, we generated $38.3 million and $36.1 million of net income and adjusted operating income, respectively, a 9.4% and 8.8% return on equity and adjusted return on equity, respectively and a 11.9% and 11.2% return on tangible equity and adjusted return on tangible equity, respectively. We have one reportable segment through which we offer a broad array of insurance coverages to a number of market niches. In order to provide a clear overview of this segment, we provide a presentation of our eight distinct underwriting divisions. Each of the underwriting divisions has dedicated underwriting leadership supported by high-quality technical staff with deep experience in their respective niches. We believe this structure and expertise allow us to serve the needs of our customers effectively and be a value-add partner to our distributors, while earning attractive risk-adjusted returns. --- Accident & Health: Our Accident & Health (“A&H”) underwriting division provides medical stop loss solutions targeting organizations with less than 2,500 employees that are actively seeking to take control of their healthcare costs by self-insuring a portion of their healthcare insurance. We write these products on an admitted basis and distribute primarily through retail brokers and wholesale broker partners. Captives: Our Captives underwriting division provides group captive solutions by drawing on our underwriting and claims expertise from other underwriting divisions to create group captives for companies seeking to self-insure. Our Captive underwriting division writes property, general liability, commercial auto, excess liability, and workers’ compensation lines of business on an E&S and an admitted basis. We often administer this business through partnerships with third-party captive managers. Global Property: Our Global Property underwriting division provides property-only solutions to large multi-jurisdictional entities with complex property exposures. The business is written entirely on an E&S basis. We distribute this product through retail brokers and select wholesale brokers. Industry Solutions: Our Industry Solutions underwriting division includes three underwriting units that each provide multiple coverages to the businesses they serve: Construction, Energy and Specialty Trucking. Coverages include general liability, excess liability, commercial auto, workers’ compensation, and inland marine. Our Construction and Energy underwriting units write principally on an admitted basis, while our Specialty Trucking unit writes on an E&S basis. We distribute these products through retail agents and brokers and a select network of wholesalers. Professional Lines: Our Professional Lines underwriting division includes three underwriting units: Management Liability, Professional Liability, and Allied Health. Professional Liability and Allied Health provide E&S primary and excess claims-made liability products distributed exclusively through wholesale brokers, while our Management Liability unit provides both E&S and admitted products distributed through both wholesale and retail brokers. Programs: Our Programs underwriting division partners with program administrators who typically possess a competitive advantage (owing to their scale in a particular market niche and/or proprietary technology) that we believe would be difficult for us to replicate on our own. The combination of our underwriting and claims expertise with their scale and/or technology creates a more powerful partnership than either party could present to the market on its own. Our Programs underwriting division writes property, general liability, commercial auto, excess liability, and workers’ compensation lines of business on an E&S and an admitted basis. Surety: Our Surety underwriting division provides contract and commercial surety solutions to a range of trade and services organizations requiring bonding. We principally focus on small to medium sized enterprises with aggregate bond programs up to $50 million. Within our Surety underwriting division, we distribute admitted-only products through retail agents and brokers. Transactional E&S: Our Transactional E&S underwriting division provides primary and excess non-catastrophe prone property and general liability solutions, with particular emphasis on risks that are considered hard to place because of the complexity of the underlying exposure, loss history, and/or limited operating history (i.e., start up and newer businesses). We access the market in this division exclusively through wholesale brokers. Our gross written premiums for each of our underwriting divisions for the nine months ending September 30, 2022 and 2021 are as follows: Total Gross Written Premiums For the nine months ended September 30, ($ in thousands) 2022 % of Total 2021 % of Total Industry Solutions $ 202,237 23.0% $ 150,599 21.0% Global Property 177,565 20.2% 140,815 19.7% Programs 131,752 15.0% 110,301 15.4% Accident & Health 97,107 11.0% 83,542 11.7% Captives 97,580 11.1% 70,355 9.8% Professional Lines 62,127 7.1% 44,060 6.2% Surety 53,734 6.1% 33,396 4.7% Transactional E&S 52,645 6.0% 17,492 2.4% Total continuing business $ 874,746 99.5% $ 650,560 90.9% Exited business 4,373 0.5% 65,116 9.1% Total gross written premiums $ 879,119 100.0% $ 715,676 100.0% Within every underwriting division, our actions are intentional to “Rule Our Niche.” We aim to innovate constantly, and our actions are specific to each of our divisions and the markets we serve. Some notable highlights are: • SkyDrive: Within our Specialty Trucking underwriting unit, we developed the award-winning, proprietary SkyDrive underwriting and risk management portal for our underwriters, brokers, and insureds to address a market that has been disrupted for some time due to the loss experience of certain incumbent carriers operating in the market. Our portal synthesizes real-time intelligence on driver and fleet history, safety, and performance, utilizing telematics and other data from a variety of sources. We believe the portal significantly increases the power of our risk selection, underwriting, risk management and claims decision-making. Given the success of SkyDrive, we have started to deploy components of SkyDrive across our commercial auto exposures in other underwriting divisions as well. • Quick-Strike: Across all of our commercial auto lines, we utilize an innovative “quick strike” response to claims events. We seek to have an experienced investigator at the scene of an accident within two hours of the event, regardless of the location, to access, and if appropriate, to resolve quickly any third-party claims. • SkyVantage: Within our Accident & Health underwriting division, we have deployed SkyVantage, our latest technology driven stop-loss solution. SkyVantage leverages big data and machine learning to evaluate group health risk at a deeper level, particularly for smaller accounts (those with less than 250 lives) for which we believe efficient data capture and data fidelity are critical to the underwriting process. We utilize SkyVantage to facilitate risk scoring to augment our experienced underwriters’ analyses for risk selection and pricing. • Cannabis Industry: As part of our focus on underserved markets, we identified the cannabis industry as a market niche not sufficiently served by the P&C insurance industry. In property and general liability lines, we elected to partner with a technology-forward program administrator with specific capabilities for the cannabis industry. We subsequently developed and launched cannabis specific professional and executive liability products we offer directly to our wholesale partners, and then further developed and launched cannabis specific commercial surety products. We identified, evaluated, and launched products across these underwriting divisions in less than six months. We believe we have one of the market leading product offerings for cannabis, one of the fastest growing industries in the United States as measured by sales and job creation. • Construction Captive: Together with our distribution partners for our Construction underwriting unit, we identified an opportunity to leverage our market leading experience and capabilities in a particular specialty contractor segment. We subsequently developed and launched an innovative captive solution for this segment which is offered side-by-side with our traditional guaranteed cost product. As a result, we have significantly broadened the portion of this market we can serve while leveraging our existing underwriting, claims and analytic expertise. In addition to the underwriting divisions listed above in the nine months ended September 30, 2022, and prior, we wrote premiums in certain markets and lines of business that we have since exited and placed into run-off following a determination that they did not fit our “Rule Our Niche” strategy. For example, in the year ended December 31, 2020, we initiated a review of our business lines leading to our exiting specialty workers’ compensation, lawyers’ professional liability, automobile dealers programs, insurance agents and brokers professional liability, title agents professional liability, commercial auto for the timber industry and liability solutions for the hospitality industry. We refer to these lines and businesses, along with others we previously exited, as our “exited business.” Gross written premiums in “exited business” was $4.4 million and $65.1 million for the nine months ended September 30, 2022 and 2021, respectively, representing 0.5% and 9.1% of our total gross written premiums for each of these periods. Gross written premiums in “exited business” was $72.0 million and $225.3 million for the years ended December 31, 2021 and 2020, respectively, representing 7.7% and 25.8% of our total gross written premiums for each of these years. --- We believe that our claims operations are a key competitive differentiator. Aligning with our focus on specific customer segments and niches, our claims management teams are highly specialized to ensure that they can apply their expertise in handling claims for each niche we serve. Our claims operations are primarily staffed by Skyward Specialty employees, allowing us to maintain full control of the claims-handling process, meet our high-quality standards, and manage our losses and LAE. For the nine months ended September 30, 2022, we handled 74.3% of our claims in-house, measured as a percentage of gross reported losses. In the limited instances where we do not handle claims in-house, we utilize claims adjusters through a third-party administrator (“TPA”). Specifically, we utilize these TPAs for a select set of captives and programs for which the TPA possesses specific expertise that we would not seek to replicate. We also utilize these TPAs for the workers’ compensation line of business, given the specific geographical knowledge that is required to adjudicate these claims. We strategically purchase reinsurance from third parties which enhances our business by protecting capital from severity events (either large single event losses or catastrophes) and volatility in our earnings. As of September 30, 2022, 98% of our reinsurance recoverables were either derived from reinsurers rated “A-” (Excellent) by A.M. Best, or better, or were collateralized for our reinsurance recoverable by the reinsurer. We treat our reinsurers as long-term partners. As such, we target underwriting profitability on a gross basis before utilization of reinsurance to ensure consistent support from our reinsurance partners and to protect ourselves from changes in the reinsurance market. Our reinsurance includes quota share, facultative, and excess of loss coverages. Based upon our modeling, it would take an event beyond our 1 in 250-year Probable Maximum Loss (“PML”) to exhaust our $25.0 million property catastrophe coverage. Additionally, we seek to expose no more than 3.0% of our stockholders’ equity to a catastrophic loss that is less than a 1 in 250-year event. We believe a strong balance sheet is foundational to our ability to deliver superior financial performance and returns as it underpins our distribution partners’ and customers’ confidence in our business. Our insurance liabilities consist of losses and LAE reserves including cost of claims reported to us (“case reserves”) and estimates of cost of claims that have been incurred but not yet reported (“IBNR”). To illustrate our reserve strength, our net IBNR reserves as a percentage of total net losses and LAE reserves was 62.2% as of September 30, 2022, up from 60.0% as of December 31, 2021, and up from 57.3% as of December 31, 2020. A centerpiece of our strong balance sheet is our rigorous reserving practices designed and overseen by experienced claims professionals and actuaries. Since 2020, we have focused on materially strengthening both the quality of our claims team and the processes and guidelines by which case reserves are set and managed. In this regard, our entire claims team works diligently to identify and recognize loss exposures as early as possible in the claims-handling process. For example, our reserving guidelines direct our adjusters to use their best estimate to set liability reserves to an expected ultimate loss within 90 days of first notice of loss. Similarly, we have invested considerably in our actuarial team, increasing the number of members of our actuarial team by fifty percent (50%) since January 1, 2020. The actuarial team has monthly meetings with each of the underwriting divisions and our claims professionals, to discuss trends inclusive of, loss frequency, severity, rate and retention by class and line of business. Additionally, we put in place rigorous risk oversight measures including the formation of a reserve committee that meets twice a quarter. We measure each of the key loss metrics by policy year against prior policy years at the same development ages to ensure the business is performing as expected. Additionally, in 2020, we entered into a LPT agreement covering policy years 2017 and prior to limit our exposure to potential loss reserve development on the covered business produced during those years. The LPT agreement covers the majority of our exited business. This protection has allowed our management team to focus on our continuing business which we believe provides the best path for continued profitable growth. The following graphic depicts the Loss Ratios, Expense Ratios and Combined Ratios for the nine months ended September 30, 2022 versus September 30, 2021 on a reported and adjusted basis. --- We believe our recent underwriting results begin to highlight the impact these initiatives have had on our business and position us to deliver consistently attractive underwriting results across P&C market cycles. We complement our strong reserve position with a conservative investment portfolio overseen by our Investment Committee. Our portfolio is mainly comprised of cash and cash equivalents and investment-grade fixed-maturity securities, supplemented by additional investments that fit our risk appetite, principally higher yielding direct lending strategies and equities. Other investments, while typically not rated securities, are generally lower volatility fixed income loans and securities that we believe provide us with risk-adjusted returns above what is achievable in liquid investment grade markets. We call this part of our investment portfolio Opportunistic Fixed Income. Our fixed maturity securities, including both core fixed income and opportunistic fixed income, together comprising 72.9% of our total investments and cash as of September 30, 2022, had a weighted average effective duration of 3.2 years as of September 30, 2022, and an average core fixed income credit rating of “AA” (Standard & Poor’s) as of September 30, 2022. We seek to maintain an “A-” (Excellent) or better financial strength rating with A.M. Best, which we carry today with a stable outlook. This is the fourth highest of 16 ratings assigned by A.M. Best to insurance companies. Maintaining a strong rating from A.M. Best helps us demonstrate our financial strength to policyholders and distribution partners, which we believe is a critical factor in the decision to purchase insurance. Skyward Specialty Insurance Group, Inc. is an insurance holding company incorporated in Delaware that was organized in 2006. Our principal executive office is located at 800 Gessner Road, Suite 600, Houston, TX.

AI Analysis | Feedback

Here are 1-3 brief analogies for Skyward Specialty Insurance (SKWD):

  • It's like a more concentrated version of Chubb, specializing in unique and complex business insurance.
  • If State Farm is your local car and home insurer, Skyward is like a specialized commercial insurer for unique business risks, similar to a focused division of AIG or Travelers.

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  • Casualty Insurance: Provides coverage for liability arising from injuries to others or damage to their property, often including general liability, commercial auto, and umbrella coverage for specialized risks.
  • Surety Bonds: Guarantees the performance of an obligation or contract by one party to another, frequently used in construction, commercial, and judicial contexts.
  • Professional Lines Insurance: Protects professionals and businesses against claims of negligence, errors, or omissions in their professional services, such as Directors & Officers (D&O) and Errors & Omissions (E&O).
  • Property Insurance: Covers commercial property against physical loss or damage from various perils, including fire, natural disasters, and other specified risks in niche markets.
  • Energy Insurance: Offers specialized coverage tailored to the unique and complex risks of the energy industry, encompassing upstream, midstream, and downstream operations.

AI Analysis | Feedback

Skyward Specialty Insurance (SKWD) primarily sells its insurance products to **other companies (B2B)**, rather than directly to individuals.

Due to the nature of its business as a specialty insurer, Skyward Specialty serves a highly diversified portfolio of insured businesses across numerous industries and niche segments. Therefore, it does not typically have a small number of identifiable "major customers" in the traditional sense, nor does it publicly disclose the names of its insured entities. Instead, its customer base consists of a broad array of businesses and organizations that require specialized property and casualty insurance solutions.

Based on Skyward Specialty's business segments and target markets, its customers can be categorized as various types of companies, including but not limited to:

  • Professional Services Firms: Companies operating in sectors such as legal, accounting, architecture, engineering, consulting, and finance, seeking coverage like professional liability (Errors & Omissions - E&O), directors & officers (D&O), and cyber insurance.
  • Healthcare Providers & Organizations: Hospitals, clinics, physician groups, and other healthcare facilities requiring specialized professional liability, general liability, and D&O coverages.
  • Commercial & Industrial Businesses: A wide range of businesses across various industries needing commercial general liability, excess liability, commercial auto, niche workers' compensation programs, commercial property, and surety bonds (e.g., construction contractors, manufacturers, specialized service providers).
  • Marine & Logistics Companies: Businesses involved in ocean and inland marine operations, including cargo owners, vessel operators, and other entities in the supply chain requiring marine hull, cargo, and liability coverages.

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Andrew Robinson, Chief Executive Officer

Andrew Robinson has served as the Chief Executive Officer of Skyward Specialty Insurance since May 2020 and as Chairman of its Board since December 2023. With over 30 years of experience as a global insurance executive, he has a track record of growth, financial improvement, and strategic and operational leadership. Prior to Skyward Specialty, Mr. Robinson spent ten years at The Hanover Insurance Group, Inc., where his roles included President of Specialty Insurance, Executive Vice President of Corporate Development, and Chief Risk Officer. While at Hanover, he was responsible for acquisitions and divestitures. He also served as Global Chief Operating Officer and Executive Vice-President at Crawford & Co. Earlier in his career, he was the managing partner of Global Insurance at Diamond (now PWC) Consulting and an Executive in Residence and Senior Advisor at Oak HC/FT, a private equity firm. He was also previously Chairman of Groundspeed Analytics, Inc. and WeGoLook LLC, and an advisor at Manchesterstory Group LLC, a venture capital firm.

Mark Haushill, EVP & Chief Financial Officer

Mark Haushill joined Skyward Specialty Insurance in 2015 as Executive Vice President and Chief Financial Officer. He brings over 25 years of experience in the insurance industry, ensuring all financial aspects of the company are managed and reported properly. Before his time at Skyward Specialty, Mr. Haushill served as Vice President, Chief Financial Officer, and Treasurer at American Safety Holdings, Ltd., a public insurance company, from September 2009. His career also includes experience at USAA, Argo Insurance Company, and as Chief Financial Officer, Treasurer & Senior VP at Argonaut Group, Inc. from 2000 to 2009. He previously served as Chief Executive Officer of North American Insurance Leaders, Inc.

Dan Bodnar, Chief Information & Technology Officer

Dan Bodnar serves as the Chief Information & Technology Officer, responsible for leading the company's information and technology strategies.

Sandip Kapadia, Executive Vice President, Chief Actuary & Analytics Officer

Sandip Kapadia holds the position of Executive Vice President, Chief Actuary & Analytics Officer, overseeing the company's actuarial and analytics functions.

Sean Duffy, EVP & Chief Claims Officer

Sean Duffy is the EVP & Chief Claims Officer at Skyward Specialty Insurance, responsible for the company's claims operations and strategy.

AI Analysis | Feedback

The key risks to Skyward Specialty Insurance (SKWD) primarily revolve around the inherent challenges of the insurance industry, competitive pressures, and evolving regulatory landscapes.

  1. Underwriting Risk and Claims Volatility: As a specialty insurance provider, Skyward Specialty faces significant challenges in accurately assessing and pricing unique and complex risks. Inaccurate underwriting can lead to inappropriate premium rates and substantial underwriting losses, which directly impact the company's financial performance. Specialty insurance lines are often characterized by higher unpredictability and a greater propensity for "blow ups" compared to standard insurance. Concerns related to claims volatility and increases in loss reserves have been highlighted in recent reports.
  2. Intense Industry Competition: The insurance industry is highly competitive, with numerous players vying for market share. Skyward Specialty, with a relatively modest market share within specialty insurance lines, must continuously differentiate its offerings to compete effectively. This intense competition can exert pressure on profit margins, make it challenging to price products adequately, and affect the company's ability to retain business.
  3. Regulatory Changes and Compliance Costs: The insurance sector is subject to a complex and stringent web of regulations at both state and federal levels. Any changes in these regulations, particularly concerning claims handling and capital requirements, can impose additional operational costs and necessitate significant adjustments to the company's compliance strategies. Staying abreast of and adapting to these evolving regulatory demands is crucial for maintaining market position and financial stability.

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AI Analysis | Feedback

Skyward Specialty Insurance (SKWD) operates within the broad specialty insurance market, offering a diverse range of commercial property and casualty products and solutions on both non-admitted and admitted bases. The company focuses on niche markets requiring highly specialized and customized underwriting solutions, including general liability, excess liability, professional liability (including cyber insurance), commercial auto, group accident & health, property, agriculture, surety, and workers' compensation.

The company's nine underwriting divisions encompass areas such as Accident & Health, Agriculture & Credit (re)Insurance, Captives, Construction & Energy Solutions, Global Property, Professional Lines, Specialty Programs, Surety, and Transactional Excess & Surplus (E&S). Within its Specialty Programs, Skyward offers coverages for areas like Aviation, Mono-line Flood, Cannabis, Crane and Rigging, Ocean Marine, Earthquake DIC, Transactional Liability, and Trade Credit.

Addressable Market Sizes:

For its main products and services, Skyward Specialty Insurance addresses the following market segments:

  • Global Specialty Insurance Market: The global specialty insurance market was valued at approximately USD 139.74 billion in 2025 and is projected to reach around USD 335.86 billion by 2034, growing at a Compound Annual Growth Rate (CAGR) of 10.23% from 2025 to 2034. Other estimates for the global specialty insurance market include USD 134.6 billion in 2025, expected to expand to USD 215.8 billion by 2030 (CAGR 9.89%).
  • U.S. Excess & Surplus (E&S) Lines Market: This is a significant area for Skyward Specialty. The U.S. E&S direct premiums written reached nearly USD 100 billion, specifically USD 98.2 billion, for full-year 2024, an increase from USD 86.6 billion in 2023. The total U.S. surplus lines industry was estimated at USD 134 billion for 2024. The U.S. E&S market accounts for over 62% of the global E&S market share.
  • Global Surety Market: The global surety market was valued at approximately USD 22.33 billion in 2024 and is projected to grow to about USD 33.15 billion by 2032, with a CAGR of 5.06% from 2025 to 2032. Another source estimates the global surety market at US$ 20.26 billion in 2024, expected to reach US$ 31.85 billion by 2031 (CAGR of 6.6% during 2025–2031).

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Skyward Specialty Insurance (NASDAQ: SKWD) is poised for future revenue growth over the next 2-3 years, driven by several strategic initiatives and market dynamics:

  1. Expansion in High-Growth, Specialized Underwriting Divisions: The company has demonstrated significant expansion and consistent growth in its specialized underwriting segments. Particularly, the Agricultural business, including its product in the U.S. dairy and livestock industry, has been a substantial contributor to gross written premiums. Other key divisions showing strong growth include Accident & Health (A&H), Captives, Surety, and Specialty Programs.
  2. Strategic Acquisitions and Market Diversification: Skyward Specialty is actively pursuing acquisitions to enhance its diversification and competitive standing. A notable upcoming catalyst is the anticipated acquisition of Apollo Group, which is expected to further boost the company's market reach and offerings. Additionally, the company has been focused on expanding into complex, underserved insurance niches, such as the launch of its new Aviation underwriting unit.
  3. Development and Launch of Innovative Specialty Products: A core component of Skyward Specialty's "Rule Our Niche" strategy is the continuous creation of tailored insurance solutions to address specific market gaps. This innovation supports premium growth and helps offset competition in more commoditized lines, as evidenced by the launch of products like Skyward Specialty EndWell Protection.
  4. Enhanced Underwriting Performance and Technology Adoption: Skyward Specialty emphasizes disciplined underwriting and leveraging technology, including AI, to achieve profitable growth. This approach allows the company to capitalize on emerging risks and penetrate underserved markets effectively, leading to higher premium retention and overall revenue stability and growth.
  5. Growth in Net Investment Income: The company's net investment income has seen increases, driven by higher yields and a growing invested asset base. This financial component contributes meaningfully to total revenue, with recent reports indicating increased income from its fixed income portfolio due to favorable yields and a larger asset pool.

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Share Repurchases

  • Information regarding specific dollar amounts of share repurchases made or authorized for future periods for Skyward Specialty Insurance is not readily available within the provided search results.

Share Issuance

  • Skyward Specialty Insurance Group, Inc. completed its Initial Public Offering (IPO) on January 12, 2023, offering 4,750,000 shares of common stock at an initial public offering price of $15.00 per share.
  • The company received approximately $66.26 million in proceeds, before expenses, from its portion of the IPO.
  • Between Q2 2024 and Q2 2025, the number of issued and outstanding shares slightly increased from 40,127,908 to 40,486,656.

Inbound Investments

  • No information available regarding large inbound investments made in the company by third-parties such as strategic partners or private equity firms within the specified timeframe, beyond the initial public offering.

Outbound Investments

  • Skyward Specialty Insurance Group is acquiring Apollo Group Holdings for approximately $555 million, aiming to expand its specialty insurance lines and enhance digital and analytical capabilities.
  • This acquisition is expected to close in Q1 2026 and will be financed through a combination of cash and shares, with debt financing from Barclays for the cash component.
  • The company also entered the specialized aviation market through the acquisition of Acceleration Aviation Underwriters.

Capital Expenditures

  • No specific dollar values for capital expenditures or their primary focus are explicitly available within the provided information for Skyward Specialty Insurance.

Trade Ideas

Select ideas related to SKWD. For more, see Trefis Trade Ideas.

Unique KeyDateTickerCompanyCategoryTrade Strategy6M Fwd Rtn12M Fwd Rtn12M Max DD
WU_11212025_Dip_Buyer_FCFYield11212025WUWestern UnionDip BuyDB | FCFY OPMDip Buy with High FCF Yield and High Margin
Buying dips for companies with high FCF yield and meaningfully high operating margin
14.5%14.5%-0.4%
COIN_11212025_Monopoly_xInd_xCD_Getting_Cheaper11212025COINCoinbase GlobalMonopolyMY | Getting CheaperMonopoly-Like with P/S Decline
Large cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple
-1.5%-1.5%-1.5%
PYPL_11142025_Dip_Buyer_FCFYield11142025PYPLPayPalDip BuyDB | FCFY OPMDip Buy with High FCF Yield and High Margin
Buying dips for companies with high FCF yield and meaningfully high operating margin
-4.5%-4.5%-7.5%
V_11142025_Monopoly_xInd_xCD_Getting_Cheaper11142025VVisaMonopolyMY | Getting CheaperMonopoly-Like with P/S Decline
Large cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple
7.6%7.6%-2.7%
WD_11072025_Dip_Buyer_ValueBuy11072025WDWalker & DunlopDip BuyDB | P/E OPMDip Buy with Low PE and High Margin
Buying dips for companies with tame PE and meaningfully high operating margin
-11.1%-11.1%-12.1%
SKWD_6302025_Quality_Momentum_RoomToRun_10%06302025SKWDSkyward Specialty InsuranceQualityQ | Momentum | UpsideQuality Stocks with Momentum and Upside
Buying quality stocks with strong momentum but still having room to run
-10.3%-10.3%-22.3%

Recent Active Movers

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Peer Comparisons for Skyward Specialty Insurance

Peers to compare with:

Financials

SKWDHPQHPEIBMCSCOAAPLMedian
NameSkyward .HP Hewlett .Internat.Cisco Sy.Apple  
Mkt Price51.8523.2624.49305.0978.16273.4065.00
Mkt Cap2.121.932.6284.9309.24,074.4158.8
Rev LTM1,33855,29534,29665,40257,696408,62556,496
Op Inc LTM-3,6241,64411,54412,991130,21411,544
FCF LTM3712,80062711,85412,73396,1847,327
FCF 3Y Avg3572,9781,40011,75313,879100,5037,366
CFO LTM3783,6972,91913,48313,744108,5658,590
CFO 3Y Avg3613,6723,89613,49814,736111,5598,697

Growth & Margins

SKWDHPQHPEIBMCSCOAAPLMedian
NameSkyward .HP Hewlett .Internat.Cisco Sy.Apple  
Rev Chg LTM22.5%3.2%13.8%4.5%8.9%6.0%7.4%
Rev Chg 3Y Avg31.4%-3.9%6.5%2.6%3.7%1.8%3.2%
Rev Chg Q26.5%4.2%14.4%9.1%7.5%9.6%9.4%
QoQ Delta Rev Chg LTM6.4%1.1%3.7%2.1%1.8%2.1%2.1%
Op Mgn LTM-6.6%4.8%17.7%22.5%31.9%17.7%
Op Mgn 3Y Avg-7.4%7.2%16.4%24.2%30.8%16.4%
QoQ Delta Op Mgn LTM--0.2%-1.4%0.6%0.4%0.1%0.1%
CFO/Rev LTM28.3%6.7%8.5%20.6%23.8%26.6%22.2%
CFO/Rev 3Y Avg33.8%6.8%12.7%21.4%26.1%28.4%23.8%
FCF/Rev LTM27.8%5.1%1.8%18.1%22.1%23.5%20.1%
FCF/Rev 3Y Avg33.4%5.5%4.6%18.6%24.6%25.6%21.6%

Valuation

SKWDHPQHPEIBMCSCOAAPLMedian
NameSkyward .HP Hewlett .Internat.Cisco Sy.Apple  
Mkt Cap2.121.932.6284.9309.24,074.4158.8
P/S1.60.41.04.45.410.03.0
P/EBIT11.26.819.925.122.531.321.2
P/E14.98.6572.736.029.941.033.0
P/CFO5.65.911.221.122.537.516.2
Total Yield6.7%14.1%2.3%5.0%5.4%2.8%5.2%
Dividend Yield0.0%2.5%2.1%2.2%2.1%0.4%2.1%
FCF Yield 3Y Avg24.5%10.6%5.5%6.4%6.0%3.1%6.2%
D/E0.10.50.70.20.10.00.2
Net D/E-0.60.30.60.20.00.00.1

Returns

SKWDHPQHPEIBMCSCOAAPLMedian
NameSkyward .HP Hewlett .Internat.Cisco Sy.Apple  
1M Rtn5.8%-1.8%14.4%0.6%2.7%-1.5%1.7%
3M Rtn10.3%-11.9%2.7%7.9%17.0%7.1%7.5%
6M Rtn-8.9%-4.0%34.5%6.6%15.2%36.3%10.9%
12M Rtn0.8%-27.3%14.2%39.2%33.7%6.0%10.1%
3Y Rtn171.5%-3.8%67.7%139.0%79.5%113.4%96.5%
1M Excs Rtn2.8%-5.6%12.9%-2.2%-0.0%-3.7%-1.1%
3M Excs Rtn6.0%-16.2%-1.7%3.6%12.7%2.8%3.2%
6M Excs Rtn-21.2%-16.3%22.3%-5.7%3.0%24.0%-1.3%
12M Excs Rtn-12.1%-42.9%-0.7%25.0%19.9%-8.4%-4.6%
3Y Excs Rtn90.1%-83.5%-11.2%59.6%-1.2%28.4%13.6%

Financials

Segment Financials

Revenue by Segment
$ Mil202420232022
Delivering commercial property and casualty products insurance coverages through its underwriting1,148895636
Total1,148895636


Price Behavior

Price Behavior
Market Price$51.85 
Market Cap ($ Bil)2.1 
First Trading Date01/13/2023 
Distance from 52W High-20.2% 
   50 Days200 Days
DMA Price$47.84$51.77
DMA Trendindeterminateup
Distance from DMA8.4%0.1%
 3M1YR
Volatility37.3%36.4%
Downside Capture61.4260.52
Upside Capture95.9252.30
Correlation (SPY)19.3%30.8%
SKWD Betas & Captures as of 11/30/2025

 1M2M3M6M1Y3Y
Beta0.740.550.550.580.60-0.23
Up Beta0.220.511.041.130.620.17
Down Beta0.550.280.200.260.560.10
Up Capture146%70%50%4%38%37%
Bmk +ve Days13263974142427
Stock +ve Days9233260128380
Down Capture58%65%65%106%78%70%
Bmk -ve Days7162452107323
Stock -ve Days11193064117333

[1] Upside and downside betas calculated using positive and negative benchmark daily returns respectively
Based On 1-Year Data
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Based On 5-Year Data
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Based On 10-Year Data
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Short Interest

Short Interest: As Of Date12152025
Short Interest: Shares Quantity1,130,476
Short Interest: % Change Since 11302025-7.3%
Average Daily Volume404,113
Days-to-Cover Short Interest2.80
Basic Shares Quantity40,487,069
Short % of Basic Shares2.8%

Earnings Returns History

Expand for More
 Forward Returns
Earnings Date1D Returns5D Returns21D Returns
10/29/20251.4%4.0%5.8%
7/30/20252.3%-3.1%-2.0%
5/1/20259.4%11.3%21.3%
2/5/20253.0%1.7%0.3%
10/29/2024-0.6%-0.9%20.0%
8/5/2024-1.8%-11.5%3.9%
5/1/20240.8%4.7%5.1%
2/20/2024-1.5%5.1%6.4%
...
SUMMARY STATS   
# Positive9910
# Negative332
Median Positive2.3%4.7%7.1%
Median Negative-1.5%-3.1%-2.4%
Max Positive11.1%12.4%21.3%
Max Negative-1.8%-11.5%-2.8%

SEC Filings

Expand for More
Report DateFiling DateFiling
93020251106202510-Q 9/30/2025
6302025807202510-Q 6/30/2025
3312025507202510-Q 3/31/2025
12312024303202510-K 12/31/2024
93020241107202410-Q 9/30/2024
6302024808202410-Q 6/30/2024
3312024503202410-Q 3/31/2024
12312023401202410-K 12/31/2023
93020231109202310-Q 9/30/2023
6302023810202310-Q 6/30/2023
3312023511202310-Q 3/31/2023
12312022328202310-K 12/31/2022
123120211132023424B4 12/31/2021