Tearsheet

Skyward Specialty Insurance (SKWD)


Market Price (12/18/2025): $49.65 | Market Cap: $2.0 Bil
Sector: Financials | Industry: Property & Casualty Insurance

Skyward Specialty Insurance (SKWD)


Market Price (12/18/2025): $49.65
Market Cap: $2.0 Bil
Sector: Financials
Industry: Property & Casualty Insurance

Investment Highlights Why It Matters Which of these 2 stories sounds closer for this stock?

1. Generates cash flow

The stock generated 4% or more of the share price (called cash flow yield), and shows moderate 10-15% or more growth.

2. Riding a trend

Think Tesla during the pandemic of 2020 when EVs were riding a cultural high, or Nvidia in the current AI boom, or even Figma. These companies don’t have enough yield, or, enough growth, or both - however - they are riding a trend. They have momentum. These can be more volatile - they don’t have the floor of strong cash flow


0 Attractive yield
Total YieldTotal Yield = Earnings Yield + Dividend Yield, Earnings Yield = Net Income / Market Cap Dividend Yield = Total Dividends / Market Cap is 7.3%, ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is 3.2%, FCF Yield is 19%
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 -71%
 
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 7.3%, ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is 3.2%, FCF Yield is 19%
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 -71%
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 Generated Analysis | Feedback

Here are the key points explaining movements in Skyward Specialty Insurance (SKWD) stock during the approximate period from August 31, 2025, to December 18, 2025: 1. The appointment of Christopher Peirce to the Board of Directors on November 11, 2025, likely contributed to positive investor sentiment, coinciding with a 2.66% increase in the stock price on November 12, 2025. Peirce brings 30 years of experience in global property and casualty insurance and is anticipated to become the Chair of the Audit Committee after the 2025 financial year closes, signaling strengthened corporate governance.

2. Strong financial performance in the third quarter of 2025, reported on October 29, 2025, buoyed investor confidence. Skyward Specialty reported a net income of $45.9 million ($1.10 diluted per share), an increase from $36.7 million ($0.89 per share) in the prior year's third quarter, surpassing analyst estimates. Gross written premiums surged by 51.6% year-over-year to $606.5 million.

Show more

Stock Movement Drivers

Return vs. Risk


Price Returns Compared

 202020212022202320242025Total [1]
Returns
SKWD Return49%-3%
Peers Return19%19%16%9%28%3%138%
S&P 500 Return16%27%-19%24%23%14%108%

Monthly Win Rates [3]
SKWD Win Rate82%58%50% 
Peers Win Rate62%55%53%55%63%57% 
S&P 500 Win Rate58%75%42%67%75%73% 

Max Drawdowns [4]
SKWD Max Drawdown-12%-17% 
Peers Max Drawdown-30%-10%-12%-10%-0%-13% 
S&P 500 Max Drawdown-31%-1%-25%-1%-2%-15% 


[1] Cumulative total returns since the beginning of 2020
[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] 2025 data is for the year up to 12/17/2025 (YTD)

How Low Can It Go

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In The Past

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Preserve Wealth

Limiting losses and compounding gains is essential to preserving wealth over time.

Asset Allocation

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About Skyward Specialty Insurance (SKWD)

Better Bets than Skyward Specialty Insurance (SKWD)

Trade Ideas

Select past 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
14.6%14.6%-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
1.6%1.6%0.0%
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
-4.2%-4.2%-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
4.4%4.4%-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
-10.5%-10.5%-11.0%
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
-14.1%-14.1%-22.3%
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
14.6%14.6%-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
1.6%1.6%0.0%
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
-4.2%-4.2%-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
4.4%4.4%-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
-10.5%-10.5%-11.0%
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
-14.1%-14.1%-22.3%

Recent Active Movers

Recent Active Movers

More From Trefis

Peer Comparisons for Skyward Specialty Insurance

Peers to compare with:

Financials

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
Mkt Price49.652,151.0969.11377.9966.0547.6367.58
Mkt Cap2.027.027.58.86.112.910.8
Rev LTM1,33816,14614,6451,8031,85614,5698,212
Op Inc LTM-------
FCF LTM3712,3753,3309615812,5271,668
FCF 3Y Avg3572,5353,2548884782,3451,616
CFO LTM3782,5933,3981,0155862,6231,804
CFO 3Y Avg3612,7703,3309134832,4291,671

Growth & Margins

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
Rev Chg LTM22.5%-6.6%11.3%18.1%5.2%5.4%8.3%
Rev Chg 3Y Avg31.4%13.2%10.6%32.4%4.7%7.5%11.9%
Rev Chg Q26.5%-2.5%12.0%19.0%8.4%5.6%10.2%
QoQ Delta Rev Chg LTM6.4%-0.7%2.8%4.6%2.2%1.4%2.5%
Op Mgn LTM-------
Op Mgn 3Y Avg-------
QoQ Delta Op Mgn LTM-------
CFO/Rev LTM28.3%16.1%23.2%56.3%31.6%18.0%25.7%
CFO/Rev 3Y Avg33.8%17.1%25.2%62.3%28.2%17.7%26.7%
FCF/Rev LTM27.8%14.7%22.7%53.3%31.3%17.3%25.2%
FCF/Rev 3Y Avg33.4%15.7%24.7%60.8%27.8%17.1%26.2%

Valuation

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
Mkt Cap2.027.027.58.86.112.910.8
P/S1.41.52.15.53.20.91.8
P/EBIT10.28.211.916.213.59.011.1
P/E13.611.516.020.817.012.614.8
P/CFO5.19.39.09.710.24.89.1
Total Yield7.3%8.7%7.9%5.0%9.9%16.2%8.3%
Dividend Yield0.0%0.0%1.7%0.2%4.0%8.3%0.9%
FCF Yield 3Y Avg24.5%12.0%14.5%8.8%7.4%19.4%13.3%
D/E0.10.20.10.00.00.30.1
Net D/E-0.7-0.3-0.8-0.2-0.3-0.0-0.3

Returns

SKWDMKLWRBKNSLRLICNAMedian
NameSkyward .Markel WR Berkl.Kinsale .RLI CNA Fina. 
1M Rtn2.4%5.3%-8.9%-2.9%8.2%4.0%3.2%
3M Rtn6.2%11.6%-3.8%-12.2%4.5%4.2%4.4%
6M Rtn-13.2%10.3%-2.6%-17.9%-4.2%7.7%-3.4%
12M Rtn-3.6%25.8%20.6%-22.9%-17.5%6.6%1.5%
3Y Rtn-71.6%56.7%37.3%14.5%47.3%47.3%
1M Excs Rtn1.7%4.6%-9.7%-3.7%7.5%3.3%2.5%
3M Excs Rtn2.3%9.3%-5.2%-12.9%2.7%2.3%2.3%
6M Excs Rtn-25.6%-2.1%-15.0%-30.3%-16.6%-4.7%-15.8%
12M Excs Rtn-15.9%12.8%6.8%-36.4%-30.5%-5.5%-10.7%
3Y Excs Rtn--2.0%-16.1%-34.8%-55.6%-25.1%-25.1%

Financials

Segment Financials

Revenue by Segment

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


Price Behavior

Short Interest

Short Interest: As Of Date11282025
Short Interest: Shares Quantity1,219,000
Short Interest: % Change Since 111520250.5%
Average Daily Volume337,032
Days-to-Cover Short Interest3.62
Basic Shares Quantity40,487,069
Short % of Basic Shares3.0%

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