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Skyward Specialty Insurance (SKWD)


Market Price (6/7/2026): $45.955 | Market Cap: $2.0 BilSector: Financials | Industry: Property & Casualty Insurance

Skyward Specialty Insurance (SKWD)


Market Price (6/7/2026): $45.955
Market Cap: $2.0 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 8.7%, ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is 4.5%, FCF Yield is 21%

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 -66%

Strong revenue growth
Rev Chg LTMRevenue Change % Last Twelve Months (LTM) is 29%

Attractive cash flow generation
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 27%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 27%

Low stock price volatility
Vol 12M is 34%

Megatrend and thematic drivers
Megatrends include Cybersecurity, Fintech & Digital Payments, and Energy Transition & Decarbonization. Themes include Cloud Security, Show more.

Weak multi-year price returns
2Y Excs Rtn is -17%

Key risks
SKWD key risks include [1] the challenge of accurately pricing unique, 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 8.7%, ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is 4.5%, FCF Yield is 21%
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 -66%
2 Strong revenue growth
Rev Chg LTMRevenue Change % Last Twelve Months (LTM) is 29%
3 Attractive cash flow generation
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 27%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 27%
4 Low stock price volatility
Vol 12M is 34%
5 Megatrend and thematic drivers
Megatrends include Cybersecurity, Fintech & Digital Payments, and Energy Transition & Decarbonization. Themes include Cloud Security, Show more.
6 Weak multi-year price returns
2Y Excs Rtn is -17%
7 Key risks
SKWD key risks include [1] the challenge of accurately pricing unique, Show more.

Valuation, Metrics & Events

Price Chart

Why The Stock Moved

Qualitative Assessment

AI Analysis | Feedback

Updated on 6/1/2026

Skyward Specialty Insurance (SKWD) stock has remained largely at the same level since 2/28/2026 because of the following key factors:

1. Mixed Q1 2026 Earnings Report with Revenue Miss.

While Skyward Specialty Insurance reported a strong operating earnings per share (EPS) of $1.25 for Q1 2026, surpassing analyst estimates ranging from $1.10 to $1.14 by 9.45% to 13.64%, its reported revenue of $475.87 million, despite a 9.9% year-over-year increase, missed a higher consensus estimate of $665.12 million. This discrepancy, particularly the revenue miss against elevated expectations, likely contributed to investor caution following the May 5/6, 2026 earnings release.

2. Analyst Downgrades and Price Target Reductions.

Leading into and during the specified period, several analyst firms adjusted their outlook for Skyward Specialty Insurance. Piper Sandler lowered its price objective for SKWD from $65.00 to $55.00, maintaining an "overweight" rating, on February 26, 2026. Additionally, Weiss Ratings downgraded the stock from a "buy" to a "hold" rating on March 19, 2026, following a similar downgrade by Zacks Research from "strong-buy" to "hold" in early February 2026. These revised ratings and reduced price targets likely exerted downward pressure on the stock.

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Stock Movement Drivers

Fundamental Drivers

The -1.1% change in SKWD stock from 2/28/2026 to 6/6/2026 was primarily driven by a -13.7% change in the company's P/E Multiple.
(LTM values as of)22820266062026Change
Stock Price ($)46.4745.96-1.1%
Change Contribution By: 
Total Revenues ($ Mil)1,3381,56617.0%
Net Income Margin (%)10.6%11.3%7.5%
P/E Multiple13.311.5-13.7%
Shares Outstanding (Mil)4044-8.9%
Cumulative Contribution-1.1%

LTM = Last Twelve Months as of date shown

Market Drivers

2/28/2026 to 6/6/2026
ReturnCorrelation
SKWD-1.1% 
Market (SPY)7.8%13.5%
Sector (XLF)2.2%50.4%

Fundamental Drivers

The -6.1% change in SKWD stock from 11/30/2025 to 6/6/2026 was primarily driven by a -18.1% change in the company's P/E Multiple.
(LTM values as of)113020256062026Change
Stock Price ($)48.9645.96-6.1%
Change Contribution By: 
Total Revenues ($ Mil)1,3381,56617.0%
Net Income Margin (%)10.6%11.3%7.5%
P/E Multiple14.011.5-18.1%
Shares Outstanding (Mil)4044-8.9%
Cumulative Contribution-6.1%

LTM = Last Twelve Months as of date shown

Market Drivers

11/30/2025 to 6/6/2026
ReturnCorrelation
SKWD-6.1% 
Market (SPY)8.5%9.5%
Sector (XLF)-1.1%27.9%

Fundamental Drivers

The -27.5% change in SKWD stock from 5/31/2025 to 6/6/2026 was primarily driven by a -44.0% change in the company's P/E Multiple.
(LTM values as of)53120256062026Change
Stock Price ($)63.3545.96-27.5%
Change Contribution By: 
Total Revenues ($ Mil)1,2141,56629.0%
Net Income Margin (%)10.2%11.3%11.0%
P/E Multiple20.511.5-44.0%
Shares Outstanding (Mil)4044-9.6%
Cumulative Contribution-27.5%

LTM = Last Twelve Months as of date shown

Market Drivers

5/31/2025 to 6/6/2026
ReturnCorrelation
SKWD-27.5% 
Market (SPY)26.6%13.8%
Sector (XLF)4.2%34.8%

Fundamental Drivers

The 94.7% change in SKWD stock from 5/31/2023 to 6/6/2026 was primarily driven by a 0.0% change in the company's P/E Multiple.
(LTM values as of)53120236062026Change
Stock Price ($)23.6145.9694.7%
Change Contribution By: 
Total Revenues ($ Mil)1,5660.0%
Net Income Margin (%)11.3%0.0%
P/E Multiple11.50.0%
Shares Outstanding (Mil)3844-15.4%
Cumulative Contribution0.0%

LTM = Last Twelve Months as of date shown

Market Drivers

5/31/2023 to 6/6/2026
ReturnCorrelation
SKWD94.7% 
Market (SPY)83.4%24.6%
Sector (XLF)72.8%39.2%

Return vs. Risk

Price Returns Compared

 202120222023202420252026Total [1]
Returns
SKWD Return--77%49%1%-14%131%
Peers Return19%16%9%28%4%-14%72%
S&P 500 Return27%-19%24%23%16%11%102%

Monthly Win Rates [3]
SKWD Win Rate--75%58%50%33% 
Peers Win Rate55%53%55%63%57%43% 
S&P 500 Win Rate75%42%67%75%67%67% 

Max Drawdowns [4]
SKWD Max Drawdown----15%-31%-19% 
Peers Max Drawdown-15%-22%-20%-15%-21%-20% 
S&P 500 Max Drawdown-5%-25%-10%-8%-19%-9% 


[1] Cumulative total returns since the beginning of 2021
[2] Peers: MKL, WRB, KNSL, RLI, CNA.
[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] 2026 data is for the year up to 6/5/2026 (YTD)

How Low Can It Go

EventSKWDS&P 500
2023 SVB Regional Banking Crisis
  % Loss-13.8%-6.7%
  % Gain to Breakeven16.0%7.1%
  Time to Breakeven15 days31 days

Compare to MKL, WRB, KNSL, RLI, CNA

In The Past

Skyward Specialty Insurance's stock fell -4.7% during the 2025 US Tariff Shock. Such a loss loss requires a 4.9% gain to breakeven.

Preserve Wealth

Limiting losses and compounding gains is essential to preserving wealth.

Asset Allocation

Actively managed asset allocation strategies protect wealth. Learn more.

Event

Compare to MKL, WRB, KNSL, RLI, CNA

In The Past

Skyward Specialty Insurance's stock fell -4.7% during the 2025 US Tariff Shock. Such a loss loss requires a 4.9% gain to breakeven.

Preserve Wealth

Limiting losses and compounding gains is essential to preserving wealth.

Asset Allocation

Actively managed asset allocation strategies protect wealth. Learn more.

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 1-2 brief analogies for Skyward Specialty Insurance (SKWD):

  • A more tech-driven W.R. Berkley, specializing in underserved and hard-to-place commercial insurance niches.

  • Markel for the modern era, using advanced data and specialized expertise to provide tailored insurance for unique, complex business risks.

AI Analysis | Feedback

  • Accident & Health Insurance: Provides medical stop loss solutions for organizations looking to self-insure a portion of their healthcare costs, augmented by SkyVantage technology.
  • Captive Solutions: Offers group captive programs, including a specific Construction Captive, enabling companies to self-insure various P&C lines.
  • Global Property Insurance: Delivers specialized property-only insurance for large, multi-jurisdictional entities with complex exposures.
  • Industry-Specific Commercial P&C Insurance: Provides comprehensive coverages, such as general liability, commercial auto, and workers' compensation, tailored for the Construction, Energy, and Specialty Trucking sectors (utilizing SkyDrive).
  • Professional Lines Insurance: Includes management liability, professional liability, and allied health claims-made liability products for various professionals and organizations.
  • Programs Insurance: Collaborates with program administrators to offer a range of property, general liability, commercial auto, excess liability, and workers' compensation lines.
  • Surety Bonds: Provides contract and commercial surety solutions (bonding) primarily for small to medium-sized enterprises.
  • Transactional E&S Insurance: Offers primary and excess non-catastrophe prone property and general liability solutions for complex, hard-to-place, or new businesses.
  • Cannabis Industry Insurance: Develops and offers specialized property, general liability, professional & executive liability, and commercial surety products for the growing cannabis market.

AI Analysis | Feedback

Skyward Specialty Insurance (SKWD) primarily sells its insurance products and solutions to other companies and organizations, rather than to individuals. The company does not list specific customer names (public or private) in the provided description, but rather describes the types of businesses and market niches it serves.

Based on the company's "Rule Our Niche" strategy and its various underwriting divisions, Skyward Specialty Insurance serves the following major categories of business customers:

  1. Businesses in Specialized & Underserved Industries: These include companies operating in sectors such as construction, energy, and specialty trucking, as well as large multi-jurisdictional entities with complex property exposures. Skyward Specialty also explicitly targets businesses in the growing cannabis industry, offering tailored property, general liability, professional liability, and surety products. These customers typically require highly specialized, customized underwriting solutions due to the unique nature of their operations or market dislocation.
  2. Small to Medium-Sized Enterprises (SMEs) and Organizations Seeking Alternative Risk Transfer or Healthcare Cost Control Solutions: This category encompasses organizations with less than 2,500 employees seeking medical stop-loss solutions to self-insure a portion of their healthcare costs. It also includes companies seeking group captive solutions for various lines of business and small to medium-sized trade and services organizations requiring contract and commercial surety bonds. These customers are looking for flexible and tailored approaches to managing their specific risks and costs.
  3. Companies with Complex, "Hard-to-Place" Risks or Specialized Liability Needs: Skyward Specialty serves businesses that are considered difficult to insure due to factors such as complex underlying exposures, challenging loss histories, or limited operating histories (e.g., start-ups and newer businesses). Additionally, this category includes businesses and professionals requiring specialized liability coverages, such as management liability, professional liability, and allied health products. These customers often find standard insurance coverages insufficient or inadequate for their needs.

AI Analysis | Feedback

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Andrew Robinson, Chairman of the Board and Chief Executive Officer

Andrew Robinson joined Skyward Specialty in 2020 as CEO and later became Chairman of the Board. He possesses over 30 years of experience as a global insurance executive. Prior to Skyward Specialty, he served as President of Specialty Insurance, Executive Vice President of Corporate Development, and Chief Risk Officer at The Hanover Insurance Group, Inc. He was also the Global Chief Operating Officer and Executive Vice-President at Crawford & Co. Before his tenure at Hanover, he was the managing partner of Global Insurance at Diamond (now PWC) Consulting. Additionally, he held the role of 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.

Taryn Leonie McHarg, Chief Financial Officer

Taryn Leonie McHarg is the Chief Financial Officer of Skyward Specialty Insurance Group (SKWD). She was also identified as the CFO of Apollo and Deputy Chief Financial Officer of Skyward Group following the acquisition of Apollo by Skyward Specialty. She recently reported purchasing shares of the company's common stock in open-market transactions in February 2026.

John Burkhart, President, U.S. Property and Casualty

John Burkhart joined Skyward Specialty in January 2021. He brings 30 years of experience in specialty lines insurance, including management and professional liability, healthcare, financial institutions, and transactional liability. Before joining Skyward Specialty, he held various roles at QBE North America and Chubb.

Sean Duffy, Executive Vice President & Chief Claims Officer

Sean Duffy serves as the Executive Vice President and Chief Claims Officer at Skyward Specialty.

Kirby Hill, President, Industry Solutions, Specialty Programs and Captives

Kirby Hill holds the title of President for Industry Solutions, Specialty Programs, and Captives at Skyward Specialty.

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Here are the key risks to Skyward Specialty Insurance (SKWD):
  1. Risk of Adverse Loss Reserve Development: Skyward Specialty has faced and continues to manage risks related to the adequacy of its historical loss reserves. The company entered into a Loss Portfolio Transfer (LPT) agreement in 2020 covering policy years 2017 and prior to limit exposure to potential loss reserve development on covered business, much of which was subsequently exited. In February 2025, the company commuted this LPT, and at December 31, 2024, it strengthened LPT loss reserves by $25.3 million and recognized approximately $9.8 million, net of tax, of uncollectible reinsurance recoverable. This demonstrates that adverse development on these older reserves has continued to materialize, impacting financial performance.
  2. Increased Competition and Challenges in Niche Market Selection: Skyward Specialty's strategy revolves around "Rule Our Niche," focusing on underserved, dislocated, or complex markets. However, this strategy carries the inherent risk of selecting and maintaining profitable niches. The company's significant volume of "exited business," which generated gross written premiums of $225.3 million in 2020 and $72.0 million in 2021 before being placed into run-off for not fitting the strategy, highlights past challenges in this area. Furthermore, the specialty insurance market is becoming increasingly attractive, leading to intensified competition that could result in pricing pressure and potentially erode Skyward Specialty's market share or underwriting margins.
  3. Regulatory and Legislative Changes: As an insurer operating predominantly in the United States and serving various specialized markets, Skyward Specialty is susceptible to a dynamic regulatory and legislative environment. Changes in insurance laws and regulations, particularly within the specific niches the company serves, could impose additional compliance costs, necessitate changes to business practices, or limit the products and services Skyward Specialty can offer, potentially impacting its profitability and operational flexibility.

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Addressable Markets for Skyward Specialty Insurance's Main Products and Services

Skyward Specialty Insurance (SKWD) operates predominantly in the United States, offering a diversified portfolio of commercial property and casualty (P&C) products across several specialized underwriting divisions. The addressable market sizes for their main products and services, primarily within the U.S. region, are as follows: * Accident & Health (Medical Stop Loss): The U.S. stop loss insurance market was valued at approximately $26.9 billion in 2024 and is estimated to reach $113.5 billion by 2034. North America, particularly the United States, holds the largest market share in stop loss insurance. * Captives: While there is significant activity in the captive insurance market, with U.S. domestic captives increasing to 3,466 in 2024, a direct overall market size in terms of premiums for "group captive solutions" was not available. The North American captive insurance market is projected to dominate globally. * Global Property (Commercial Property): The global commercial property insurance market was valued at $254.93 billion in 2022 and is estimated to reach $724 billion by 2032. In 2023, North America was the largest regional market with over 5 million commercial building policies active. The commercial property insurance market globally grew from $378.18 billion in 2025 to $422.74 billion in 2026. * Industry Solutions: * **Construction:** The U.S. construction insurance market is valued at $13.9 billion in 2024. The global construction insurance market is expected to reach $92.0 billion by 2034, increasing from $39.2 billion in 2024, with North America holding a 37.3% market share and generating approximately $14.6 billion in revenue in 2024. * **Energy:** The global energy insurance market covered insured assets exceeding $4.2 trillion in 2024. North America leads in energy insurance uptake. The global energy insurance market size was valued at USD 6.32 million in 2025 and is projected to reach USD 8.72 million by 2033. * **Specialty Trucking (Commercial Auto):** The U.S. Commercial Auto Insurance Market size was valued at $40.45 billion in 2023 and is anticipated to exceed $90.41 billion by 2033. Globally, the commercial auto insurance market was valued at $199.9 billion in 2025 and is projected to reach $459.1 billion by 2035. North America is expected to hold a 38.8% share of the commercial auto insurance market by 2035. * Professional Lines (Professional Liability): The global professional liability insurance market is estimated at $51.4 billion in 2026 and is expected to grow to $69.2 billion by 2035. In 2024, North America dominated this market, with the U.S. accounting for more than 11 million active policies and a market size of approximately $17.1 billion. * Programs: null * Surety: The U.S. surety bond market writes approximately $7-9 billion in premiums annually. Globally, the surety market was estimated at $19.14 billion in 2024 and is projected to grow to $27.7 billion by 2035. North America is the largest market for surety bonds, accounting for approximately 60% of the global share. * Transactional E&S (Excess & Surplus Lines): The U.S. excess and surplus lines market reached just under $130 billion in 2024. For full-year 2024, the U.S. E&S direct premiums written were nearly $100 billion. In 2025, surplus lines premium volume across the 15 stamping office states totaled $90.3 billion. * Cannabis Industry Insurance: The legal U.S. cannabis industry would potentially generate about $1 billion in annual insurance premiums if insured to normal levels. The global cannabis insurance market was valued at $1.76 billion in 2024 and is expected to grow to $10 billion by 2035. North America's cannabis insurance market was valued at $1 billion in 2024 and is projected to reach $6 billion by 2035.

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Skyward Specialty Insurance (SKWD) is expected to drive future revenue growth over the next 2-3 years through several key strategies:
  1. Strategic Expansion in Niche Markets: The company's core "Rule Our Niche" strategy focuses on underserved, dislocated, and specialized markets, which provides opportunities for growth. This is evidenced by continued strong performance in divisions like Transactional E&S, Captives, Industry Solutions, and Professional Lines, and the development of specialized offerings for emerging sectors such as the cannabis industry. Additionally, Skyward Specialty has expanded its underwriting divisions to include areas like Agriculture and Credit (Re)insurance and Media Liability, further diversifying its revenue streams within specialty insurance.
  2. Impact of Strategic Acquisitions: The acquisition of Apollo Group Holdings is a significant driver, expected to expand Skyward Specialty's presence in specialty insurance lines and enhance its digital and analytical capabilities. This acquisition is also anticipated to introduce new growth areas, notably a partnership related to autonomous vehicles.
  3. Leveraging Advanced Technology and Analytics: Skyward Specialty consistently invests in and utilizes advanced technology and analytics to improve risk selection, pricing, and claims management. Proprietary platforms like SkyDrive for specialty trucking and SkyVantage for Accident & Health exemplify this approach, enabling more efficient data capture, risk scoring, and ultimately, profitable premium growth.
  4. Disciplined Underwriting and Favorable Pricing: The company's strong underwriting discipline and ability to secure favorable pricing contribute to its premium growth. Management has reported achieving mid-single-digit pure rate increases (excluding global property) and robust submission growth, indicating a healthy environment for premium expansion in their chosen niches.

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Share Repurchases

  • Skyward Specialty Insurance Group, Inc. announced a share repurchase program in October 2024, authorizing the purchase of up to $50 million of its common stock.
  • The company indicated in February 2026 that it plans to opportunistically use its share repurchase program to deploy excess capital, taking advantage of its share price.

Share Issuance

  • Skyward Specialty Insurance Group, Inc. became a public company on January 13, 2023.
  • In early 2026, shares were issued to executives and officers upon the settlement of Restricted Stock Unit (RSU) grants originating from the 2023 IPO.
  • A new US$41.7 million shelf registration for ESOP related common stock was noted in March 2026.

Outbound Investments

  • Skyward Specialty completed the acquisition of Apollo Group Holdings Limited, which expanded its capabilities by adding Lloyd's-based specialty capacity and digital-economy liability products.

Recent Active Movers

Peer Comparisons

Peers to compare with:

Financials

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
Mkt Price45.961,818.6768.57306.1252.3843.6660.47
Mkt Cap2.023.026.97.04.811.89.4
Rev LTM1,56615,88414,8191,9171,89914,7648,341
Op Inc LTM-------
FCF LTM4212,1883,3531,0145482,1641,589
FCF 3Y Avg3492,3813,3659475322,3461,647
CFO LTM4282,4013,5071,0635542,2451,654
CFO 3Y Avg3542,6253,4719775372,4341,706

Growth & Margins

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
Rev Chg LTM29.0%2.1%6.2%17.0%9.5%4.1%7.9%
Rev Chg 3Y Avg31.7%8.5%9.9%28.4%2.3%6.7%9.2%
Rev Chg Q44.4%-13.5%5.1%10.2%4.0%1.4%4.5%
QoQ Delta Rev Chg LTM10.3%-2.7%1.2%2.3%0.9%0.3%1.0%
Op Inc Chg LTM-------
Op Inc Chg 3Y Avg-------
Op Mgn LTM-------
Op Mgn 3Y Avg-------
QoQ Delta Op Mgn LTM-------
CFO/Rev LTM27.3%15.1%23.7%55.4%29.2%15.2%25.5%
CFO/Rev 3Y Avg28.8%16.3%25.3%60.5%30.9%17.3%27.0%
FCF/Rev LTM26.9%13.8%22.6%52.9%28.9%14.7%24.7%
FCF/Rev 3Y Avg28.5%14.8%24.5%58.8%30.6%16.7%26.5%

Valuation

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
Mkt Cap2.023.026.97.04.811.89.4
P/S1.31.41.83.72.50.81.6
P/Op Inc-------
P/EBIT8.59.210.810.59.67.19.4
P/E11.513.014.313.312.29.712.6
P/CFO4.89.67.76.68.75.37.1
Total Yield8.7%7.7%9.6%7.7%13.2%19.2%9.1%
Dividend Yield0.0%0.0%2.6%0.3%5.0%8.9%1.4%
FCF Yield 3Y Avg19.4%10.7%13.0%9.5%8.4%18.2%11.8%
D/E0.20.20.10.00.10.30.1
Net D/E-0.7-0.3-0.9-0.4-0.3-0.0-0.3

Returns

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
1M Rtn1.0%1.0%3.1%-0.8%10.2%1.0%1.0%
3M Rtn-5.6%-8.3%-1.9%-17.6%-11.4%-8.3%-8.3%
6M Rtn-1.4%-11.2%4.5%-14.0%-12.2%4.9%-6.3%
12M Rtn-26.4%-7.4%-5.1%-35.6%-25.1%0.5%-16.2%
3Y Rtn95.2%33.6%92.7%-13.5%-9.1%39.1%36.4%
1M Excs Rtn4.6%1.6%3.5%0.7%11.3%1.4%2.5%
3M Excs Rtn-15.2%-17.8%-11.5%-27.2%-20.9%-17.9%-17.9%
6M Excs Rtn-6.1%-19.4%-10.4%-25.9%-20.3%-6.9%-14.9%
12M Excs Rtn-51.2%-29.5%-28.6%-58.1%-48.1%-23.0%-38.8%
3Y Excs Rtn18.0%-38.3%23.1%-75.1%-79.8%-25.6%-32.0%

Comparison Analyses

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Financials

Segment Financials

Revenue by Segment
$ Mil202520242023
Broad array of commercial property and casualty products and solutions on a non-admitted (or E&S)1,148895636
Total1,148895636


Price Behavior

Price Behavior
Market Price$45.96 
Market Cap ($ Bil)2.0 
First Trading Date01/13/2023 
Distance from 52W High-26.4% 
   50 Days200 Days
DMA Price$45.29$46.68
DMA Trenddownindeterminate
Distance from DMA1.5%-1.5%
 3M1YR
Volatility32.2%34.2%
Downside Capture74.1065.80
Upside Capture26.5411.00
Correlation (SPY)25.2%16.9%
SKWD Betas & Captures as of 5/31/2026

 1M2M3M6M1Y3Y
Beta0.100.600.510.410.480.56
Up Beta1.751.270.380.370.660.67
Down Beta-1.22-1.490.430.770.510.57
Up Capture-29%22%32%10%6%24%
Bmk +ve Days13283667141432
Stock +ve Days8172656116388
Down Capture21%81%88%53%80%67%
Bmk -ve Days7132757109318
Stock -ve Days12243767131356

[1] Upside and downside betas calculated using positive and negative benchmark daily returns respectively
Based On 1-Year Data
Annualized
Return
Annualized
Volatility
Sharpe
Ratio
Correlation
with SKWD
SKWD-27.8%34.2%-0.91-
Sector ETF (XLF)4.6%14.6%0.0934.8%
Equity (SPY)25.3%12.1%1.5713.8%
Gold (GLD)27.6%26.9%0.881.1%
Commodities (DBC)36.9%19.0%1.52-9.6%
Real Estate (VNQ)12.5%13.3%0.6325.5%
Bitcoin (BTCUSD)-42.0%42.5%-1.165.8%

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Based On 5-Year Data
Annualized
Return
Annualized
Volatility
Sharpe
Ratio
Correlation
with SKWD
SKWD19.2%34.0%0.81-
Sector ETF (XLF)8.5%18.6%0.3439.7%
Equity (SPY)13.5%17.1%0.6226.4%
Gold (GLD)17.3%18.1%0.781.2%
Commodities (DBC)9.5%19.4%0.38-0.8%
Real Estate (VNQ)3.2%18.8%0.0725.2%
Bitcoin (BTCUSD)11.3%54.6%0.4010.2%

Smart multi-asset allocation framework can stack odds in your favor. Learn How
Based On 10-Year Data
Annualized
Return
Annualized
Volatility
Sharpe
Ratio
Correlation
with SKWD
SKWD9.2%34.0%0.81-
Sector ETF (XLF)12.6%22.2%0.5239.7%
Equity (SPY)15.3%17.9%0.7326.4%
Gold (GLD)13.0%16.0%0.671.2%
Commodities (DBC)7.1%18.0%0.32-0.8%
Real Estate (VNQ)5.6%20.7%0.2425.2%
Bitcoin (BTCUSD)63.3%66.9%1.0310.2%

Smart multi-asset allocation framework can stack odds in your favor. Learn How

Short Interest

Short Interest: As Of Date5152026
Short Interest: Shares Quantity1.2 Mil
Short Interest: % Change Since 4302026-3.1%
Average Daily Volume0.5 Mil
Days-to-Cover Short Interest2.7 days
Basic Shares Quantity44.5 Mil
Short % of Basic Shares2.8%

Earnings Returns History

Updated 6/7/2026
Expand for More
 Forward Returns
Earnings Date1D Returns5D Returns21D Returns
5/6/20263.8%0.4%4.8%
2/23/2026-4.4%3.0%-10.1%
10/29/20251.4%4.0%5.8%
7/30/20252.3%-3.1%-2.0%
5/1/20259.4%11.3%21.3%
2/25/2025-0.8%2.7%4.6%
10/29/2024-0.6%-0.9%20.0%
8/5/2024-1.8%-11.5%3.9%
...
SUMMARY STATS   
# Positive91111
# Negative533
Median Positive2.3%4.0%6.4%
Median Negative-1.5%-3.1%-2.8%
Max Positive11.1%12.4%21.3%
Max Negative-4.4%-11.5%-10.1%

SEC Filings

Expand for More
Report DateFiling DateFiling
03/31/202605/11/202610-Q
12/31/202503/02/202610-K
09/30/202511/06/202510-Q
06/30/202508/07/202510-Q
03/31/202505/07/202510-Q
12/31/202403/03/202510-K
09/30/202411/07/202410-Q
06/30/202408/08/202410-Q
03/31/202405/03/202410-Q
12/31/202304/01/202410-K
09/30/202311/09/202310-Q
06/30/202308/10/202310-Q
03/31/202305/11/202310-Q
12/31/202203/28/202310-K
09/30/202201/13/2023424B4

Insider Activity

Updated 5/21/2026
Expand for More
#OwnerTitleHoldingActionFiling DatePriceSharesTransacted
Value
Value of
Held Shares
Form
1Kuczinski, Anthony JDirectBuy521202647.102,00094,200752,517Form
2Ashe, Gena LDirectSell512202646.3574034,299211,820Form
3Kuczinski, Anthony JDirectBuy304202648.131,00048,132572,916Form
4Kuczinski, Anthony JDirectBuy304202648.792,00097,582531,969Form
5Kuczinski, Anthony JDirectBuy304202646.882,00093,750417,329Form
Core Cache Last Updated: 6/6/2026