Skyward Specialty [SKWD] vs Progressive [PGR] Detailed Stock Comparison

Skyward Specialty Insurance Group, Inc.

NASDAQ

Progressive Corporation

NYSE

TLDR: Quick Comparison Summary

Based on 20 vital metrics comparison: Skyward Specialty Insurance Group, Inc. wins in 8 metrics, Progressive Corporation wins in 11 metrics, with 0 ties. Progressive Corporation appears stronger overall.

View Metrics Details

Vital Metrics Comparison

Metric	Skyward Specialty Insurance Group, Inc.	Progressive Corporation	Better
P/E Ratio (TTM)	11.36	10.45	Progressive Corporation
Price-to-Book Ratio	1.86	3.75	Skyward Specialty Insurance Group, Inc.
Debt-to-Equity Ratio	11.88	26.17	Skyward Specialty Insurance Group, Inc.
PEG Ratio	0.06	1.06	Skyward Specialty Insurance Group, Inc.
EV/EBITDA	7.21	8.33	Skyward Specialty Insurance Group, Inc.
Profit Margin (TTM)	12.00%	12.93%	Progressive Corporation
Operating Margin (TTM)	17.60%	16.39%	Skyward Specialty Insurance Group, Inc.
EBITDA Margin (TTM)	17.60%	16.39%	Skyward Specialty Insurance Group, Inc.
Return on Equity	18.86%	37.90%	Progressive Corporation
Return on Assets (TTM)	3.50%	7.94%	Progressive Corporation
Free Cash Flow (TTM)	$400.62M	$17.20B	Progressive Corporation
Dividend Yield	N/A	8.67%	N/A
1-Year Return	-30.36%	-33.18%	Skyward Specialty Insurance Group, Inc.
Price-to-Sales Ratio (TTM)	1.45	1.34	Progressive Corporation
Enterprise Value	$1.74B	$126.25B	Progressive Corporation
EV/Revenue Ratio	1.23	1.41	Skyward Specialty Insurance Group, Inc.
Revenue per Share (TTM)	$35	$153	Progressive Corporation
Earnings per Share (Diluted)	$4.07	$19.65	Progressive Corporation
Beta (Stock Volatility)	0.60	0.33	Progressive Corporation
Short % of Float	3.44%	1.25%	Progressive Corporation

Skyward Specialty Insurance Group, Inc. vs Progressive Corporation Stock Performance Analysis

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Performance Comparison

Short-term Returns

Stock	1D	1W	1M	3M	6M	YTD
Skyward Specialty Insurance Group, Inc.	-3.11%	-6.68%	-2.09%	-11.39%	-5.42%	-12.11%
Progressive Corporation	-1.71%	-1.75%	-2.90%	-9.32%	-14.84%	-8.80%

Long-term Returns

Stock	1Y	3Y	5Y	10Y	15Y	20Y
Skyward Specialty Insurance Group, Inc.	-30.36%	84.76%	-14.50%	-14.50%	-14.50%	-14.50%
Progressive Corporation	-33.18%	47.03%	89.72%	479.08%	807.96%	589.11%

Performance & Financial Health Analysis: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Metric	SKWD	PGR
Market Information
Market Cap i	$2.06B	$120.11B
Market Cap Category	Mid cap	Large cap
10 Day Avg. Volume i	429,359	3,008,670
90 Day Avg. Volume i	428,633	3,010,043
Last Close	$42.73	$193.46
52 Week Range	$40.60 - $65.01	$189.20 - $289.96
% from 52W High	-34.27%	-33.28%
All-Time High	$65.05 (Jun 02, 2025)	$292.99 (Mar 17, 2025)
% from All-Time High	-34.31%	-33.97%
Growth Metrics
Quarterly Revenue Growth	0.27%	0.09%
Quarterly Earnings Growth	2.00%	0.10%
Financial Health
Profit Margin (TTM) i	0.12%	0.13%
Operating Margin (TTM) i	0.18%	0.16%
Return on Equity (TTM) i	0.19%	0.38%
Debt to Equity (MRQ) i	11.88	26.17
Cash & Liquidity
Book Value per Share (MRQ)	$24.92	$54.71
Cash per Share (MRQ)	$9.73	$3.64
Operating Cash Flow (TTM) i	$408.08M	$12.39B
Levered Free Cash Flow (TTM) i	$-67,062,124	$11.31B
Dividends
Last 12-Month Dividend Yield i	N/A	8.67%
Last 12-Month Dividend i	$0.00	$18.40

Valuation & Enterprise Metrics Analysis: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Metric	SKWD (Apr 22, 2026)	PGR (Apr 24, 2026)
Price Ratios
P/E Ratio (TTM) i	11.36	10.45
Forward P/E i	8.47	12.73
PEG Ratio i	0.06	1.06
Price to Sales (TTM) i	1.45	1.34
Price to Book (MRQ) i	1.86	3.75
Market Capitalization
Market Capitalization i	$2.06B	$120.11B
Enterprise Value i	$1.74B	$126.25B
Enterprise Value Metrics
Enterprise to Revenue i	1.23	1.41
Enterprise to EBITDA i	7.21	8.33
Risk & Other Metrics
Beta i	0.60	0.33
Book Value per Share (MRQ) i	$24.92	$54.71

Financial Statements Comparison: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Financial Metrics

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Revenue

Operating Margin

Profit Margin

Long Term Debt

Income Flow Analysis

Financial Statements Comparison

Income Statement

Metric	SKWD (2025)	PGR (2025)
Revenue/Sales i	1.42B	87.64B
Cost of Goods Sold i	N/A	N/A
COGS % of Revenue i	0.0%	0.0%
Gross Profit i	N/A	N/A
Gross Margin i	0.0%	0.0%
Research & Development i	N/A	N/A
Operating Income (EBIT) i	N/A	N/A
Operating Margin i	0.0%	0.0%
EBITDA i	N/A	N/A
EBITDA Margin i	0.0%	0.0%
Pre-Tax Income i	216.42M	14.22B
Pre-Tax Income % of Revenue i	15.2%	16.2%
Income Tax i	46.40M	2.92B
Income Tax % of Revenue i	3.3%	3.3%
Net Income (Profit) i	170.03M	11.31B
Profit Margin i	12.0%	12.9%

Balance Sheet & Liquidity Metrics

Metric	SKWD (2025)	PGR (2025)
Cash & Equivalents i	168.54M	125.00M
Total Current Assets i	N/A	N/A
Total Current Assets % of Revenue i	0.0%	0.0%
Total Current Liabilities i	N/A	N/A
Total Current Liabilities % of Revenue i	0.0%	0.0%
Long-Term Debt i	119.98M	6.90B
Long-Term Debt % of Revenue i	8.5%	7.9%
Total Shareholders Equity i	1.01B	30.32B
Retained Earnings i	267.15M	27.33B
Retained Earnings % of Revenue i	18.8%	31.2%
Property, Plant & Equipment i	N/A	N/A

Cash Flow Statement Comparison

Metric	SKWD (2025)	PGR (2025)
Operating Cash Flow i	-226.34M	12.39B
Operating Cash Flow % of Revenue i	-15.9%	14.1%
Capital Expenditures i	-5.45M	-268.00M
Free Cash Flow i	400.62M	17.20B
FCF Margin i	28.2%	19.6%
Debt Repayment i	-43.00M	N/A
Common Stock Repurchase i	N/A	-166.00M

Short Interest & Institutional Ownership Analysis

Metric	SKWD	PGR
Shares Short i	1.40M	7.29M
Short Ratio i	2.78	2.32
Short % of Float i	3.44%	1.25%
Shares Outstanding i	40.51M	584.40M
Float Shares i	40.69M	582.21M
% Held by Insiders i	8.09%	0.25%
% Held by Institutions i	87.90%	89.29%
% Held by Public i	4.01%	10.46%

Dividend Analysis & Yield Comparison: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Metric	SKWD	PGR
Last 12-Month Dividend i	$0.00	$18.40
Last 12-Month Dividend Yield i	N/A	8.67%
3-Year Avg Annual Dividend i	$0.00	$6.62
3-Year Avg Dividend Yield i	N/A	0.71%
3-Year Total Dividends i	$0.00	$19.85
Ex-Dividend Date	N/A	Jan 02, 2026

Metric	SKWD (Dec 31, 2025)	PGR (Dec 31, 2025)
Operating Cash Flow i	43.23M	3.63B
Operating Cash Flow % of Revenue i	11.2%	16.0%
Capital Expenditures i	-1.71M	-111.00M
Free Cash Flow i	50.06M	3.05B
FCF Margin i	13.0%	13.4%
Debt Repayment i	-43.00M	N/A
Common Stock Repurchase i	N/A	-59.00M

Skyward Specialty [SKWD] vs Progressive [PGR] Detailed Stock Comparison

Skyward Specialty Insurance Group, Inc.

Progressive Corporation

TLDR: Quick Comparison Summary

Vital Metrics Comparison

Complete Skyward Specialty Insurance Group, Inc. Investment Analysis: Compare with Industry Leaders

Ever Wonder Which Stock is Really the Better Pick?

What You'll Actually Learn (in Plain English)

💰 Which Stock is Cheaper

🏥 Which Company is Healthier

📈 Which Has Been Growing Faster

💵 Which Pays You Better

Skyward Specialty Insurance Group, Inc. vs Progressive Corporation Stock Performance Analysis

Performance Comparison

Short-term Returns

Long-term Returns

Performance & Financial Health Analysis: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Valuation & Enterprise Metrics Analysis: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Financial Statements Comparison: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Financial Metrics

Revenue

Operating Margin

Profit Margin

Long Term Debt

Income Flow Analysis

SKWD (Annual)

SKWD (Quarterly)

PGR (Annual)

PGR (Quarterly)

Financial Statements Comparison

Income Statement

Balance Sheet & Liquidity Metrics

Cash Flow Statement Comparison

Income Statement

Balance Sheet & Liquidity Metrics

Cash Flow Statement Comparison

Short Interest & Institutional Ownership Analysis

Dividend Analysis & Yield Comparison: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Metric	SKWD (Dec 31, 2025)	PGR (Dec 31, 2025)
Revenue/Sales i	385.73M	22.74B
Cost of Goods Sold i	N/A	N/A
COGS % of Revenue i	0.0%	0.0%
Gross Profit i	N/A	N/A
Gross Margin i	0.0%	0.0%
Research & Development i	N/A	N/A
Operating Income (EBIT) i	N/A	N/A
Operating Margin i	0.0%	0.0%
EBITDA i	N/A	N/A
EBITDA Margin i	0.0%	0.0%
Pre-Tax Income i	54.65M	3.68B
Pre-Tax Income % of Revenue i	14.2%	16.2%
Income Tax i	11.42M	731.00M
Income Tax % of Revenue i	3.0%	3.2%
Net Income (Profit) i	43.23M	2.95B
Profit Margin i	11.2%	13.0%

Skyward Specialty [SKWD] vs Progressive [PGR] Detailed Stock Comparison

Skyward Specialty Insurance Group, Inc.

Progressive Corporation

TLDR: Quick Comparison Summary

Vital Metrics Comparison

Complete Skyward Specialty Insurance Group, Inc. Investment Analysis: Compare with Industry Leaders

Ever Wonder Which Stock is Really the Better Pick?

What You'll Actually Learn (in Plain English)

💰 Which Stock is Cheaper

🏥 Which Company is Healthier

📈 Which Has Been Growing Faster

💵 Which Pays You Better

Skyward Specialty Insurance Group, Inc. vs Progressive Corporation Stock Performance Analysis

Performance Comparison

Short-term Returns

Long-term Returns

Performance & Financial Health Analysis: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Valuation & Enterprise Metrics Analysis: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Financial Statements Comparison: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Financial Metrics Quarterly Annual

Revenue

Operating Margin

Profit Margin

Long Term Debt

Income Flow Analysis

SKWD (Annual)

SKWD (Quarterly)

PGR (Annual)

PGR (Quarterly)

Financial Statements Comparison

Income Statement

Balance Sheet & Liquidity Metrics

Cash Flow Statement Comparison

Income Statement

Balance Sheet & Liquidity Metrics

Cash Flow Statement Comparison

Short Interest & Institutional Ownership Analysis

Dividend Analysis & Yield Comparison: Skyward Specialty Insurance Group, Inc. vs Progressive Corporation

Financial Metrics