SKWD vs. PGR

Last updated Jun 4, 2026

SKWD (Skyward Specialty Insurance Group Inc. Common Stock) and PGR (The Progressive Corporation) are both stocks. Both operate in the Insurance - Property & Casualty industry within the Financial Services sector. Over the past 3 years, SKWD returned 21.40%/yr vs 17.80%/yr for PGR. At a 0.31 correlation, their price movements are largely independent.

Performance

SKWD vs. PGR - Performance Comparison

The chart below illustrates the hypothetical performance of a $10,000 investment in Skyward Specialty Insurance Group Inc. Common Stock (SKWD) and The Progressive Corporation (PGR). The values are adjusted to include any dividend payments, if applicable.

Returns By Period

In the year-to-date period, SKWD achieves a -16.40% return, which is significantly lower than PGR's -9.60% return.

SKWD

• 1D: -3.11%
• 1M: -2.09%
• YTD: -16.40%
• 6M: -5.42%
• 1Y: -34.08%
• 3Y*: 21.40%
• 5Y*: —
• 10Y*: —

PGR

• 1D: -1.71%
• 1M: -2.90%
• YTD: -9.60%
• 6M: -9.39%
• 1Y: -28.28%
• 3Y*: 17.80%
• 5Y*: 16.61%
• 10Y*: 22.74%

*Multi-year figures are annualized to reflect compound growth (CAGR)

SKWD vs. PGR - Yearly Performance Comparison

	2026 (YTD)	2025	2024	2023
SKWD Skyward Specialty Insurance Group Inc. Common Stock	-16.40%	1.13%	49.17%	77.38%
PGR The Progressive Corporation	-9.60%	-3.02%	51.39%	19.44%

Correlation

The correlation between SKWD and PGR is 0.34, which is low. Their price movements are largely independent, making them effective diversification partners.

	Correlation
Correlation (1Y) Calculated over the trailing 1-year period	0.34
Correlation (3Y) Calculated over the trailing 3-year period	0.31
Correlation (All Time) Calculated using the full available price history since Jan 17, 2023	0.31

Fundamentals

EPS SKWD : $5.66 PGR : $19.23
PE Ratio SKWD : 7.55 PGR : 10.06
PEG Ratio SKWD : 0.17 PGR : 0.08
PS Ratio SKWD : 0.86 PGR : 1.30
Total Revenue (TTM) SKWD : $1.56B PGR : $87.65B
Gross Profit (TTM) SKWD : $523.39M PGR : $23.23B
EBITDA (TTM) SKWD : $170.03M PGR : $14.81B

Return for Risk

SKWD vs. PGR — Risk / Return Rank

Compare risk-adjusted metric ranks to identify better-performing investments over the past 12 months.

SKWD

SKWD Risk / Return Rank: 6
SKWD Sharpe Ratio Rank: 4
SKWD Sortino Ratio Rank: 6
SKWD Omega Ratio Rank: 8
SKWD Calmar Ratio Rank: 2
SKWD Martin Ratio Rank: 8

PGR

PGR Risk / Return Rank: 3
PGR Sharpe Ratio Rank: 1
PGR Sortino Ratio Rank: 3
PGR Omega Ratio Rank: 5
PGR Calmar Ratio Rank: 0
PGR Martin Ratio Rank: 6

The rank (0–100) shows how this investment's returns compare to the risk taken. Higher = better. Based on the past 12 months of data, combining Sharpe, Sortino, and other metrics used by quantitative funds and institutional investors.

SKWD vs. PGR - Risk-Adjusted Trends Comparison

This table presents a comparison of risk-adjusted performance metrics for Skyward Specialty Insurance Group Inc. Common Stock (SKWD) and The Progressive Corporation (PGR). Risk-adjusted metrics are performance indicators that assess an investment's returns in relation to its risk, enabling a more accurate comparison of different investment options.

	SKWD	PGR	Difference
Sharpe ratio Return per unit of total volatility	-1.01	-1.28	+0.26
Sortino ratio Return per unit of downside risk	-1.42	-1.78	+0.36
Omega ratio Gain probability vs. loss probability	0.84	0.80	+0.04
Calmar ratio Return relative to maximum drawdown	-0.98	-1.01	+0.03
Martin ratio Return relative to average drawdown	-1.38	-1.46	+0.08
Data is calculated on a 1-year rolling basis and updated daily. The trend shows the change in the indicator over the past month.

SKWD vs. PGR - Sharpe Ratio Comparison

The current SKWD Sharpe Ratio is -1.01, which is comparable to the PGR Sharpe Ratio of -1.28. The chart below compares the historical Sharpe Ratios of SKWD and PGR, calculated using daily returns over the previous 12 months. A higher Sharpe Ratio indicates better risk-adjusted performance relative to the risk-free rate.

Sharpe Ratios by Period

	SKWD	PGR	Difference
Sharpe Ratio (1Y) Calculated over the trailing 1-year period	-1.01	-1.28	+0.26
Sharpe Ratio (5Y) Calculated over the trailing 5-year period	—	0.68	—
Sharpe Ratio (10Y) Calculated over the trailing 10-year period	—	0.93	—
Sharpe Ratio (All Time) Calculated using the full available price history	0.80	0.58	+0.22

Drawdowns

SKWD vs. PGR - Drawdown Comparison

The maximum SKWD drawdown since its inception was -36.52%, smaller than the maximum PGR drawdown of -71.06%. Use the drawdown chart below to compare losses from any high point for SKWD and PGR.

Drawdown Indicators

	SKWD	PGR	Difference
Max Drawdown Largest peak-to-trough decline	-36.52%	-71.06%	+34.54%
Max Drawdown (1Y) Largest decline over 1 year	-34.98%	-28.14%	-6.84%
Max Drawdown (3Y) Largest decline over 3 years	-36.52%	-30.35%	-6.17%
Max Drawdown (5Y) Largest decline over 5 years	—	-30.35%	—
Max Drawdown (10Y) Largest decline over 10 years	—	-30.35%	—
Current Drawdown Current decline from peak	-34.26%	-29.23%	-5.03%
Average Drawdown Average peak-to-trough decline	-10.89%	-14.53%	+3.64%
Ulcer Index Depth and duration of drawdowns from previous peaks	26.27%	20.72%	+5.55%

Volatility

SKWD vs. PGR - Volatility Comparison

Skyward Specialty Insurance Group Inc. Common Stock (SKWD) has a higher volatility of 10.00% compared to The Progressive Corporation (PGR) at 5.82%. This indicates that SKWD's price experiences larger fluctuations and is considered to be riskier than PGR based on this measure. The chart below showcases a comparison of their rolling one-month volatility.

Volatility by Period

	SKWD	PGR	Difference
Volatility (1M) Calculated over the trailing 1-month period	10.00%	5.82%	+4.18%
Volatility (6M) Calculated over the trailing 6-month period	24.87%	16.25%	+8.62%
Volatility (1Y) Calculated over the trailing 1-year period	33.75%	22.23%	+11.52%
Volatility (5Y) Calculated over the trailing 5-year period, annualized	33.91%	24.52%	+9.39%
Volatility (10Y) Calculated over the trailing 10-year period, annualized	33.91%	24.43%	+9.48%

Dividends

SKWD vs. PGR - Dividend Comparison

SKWD has not paid dividends to shareholders, while PGR's dividend yield for the trailing twelve months is around 7.18%.

Position	TTM	2025	2024	2023	2022	2021	2020	2019	2018	2017	2016	2015
PGR The Progressive Corporation	7.18%	2.15%	0.48%	0.25%	0.31%	6.23%	2.68%	3.89%	1.86%	1.21%	2.50%	2.16%
SKWD Skyward Specialty Insurance Group Inc. Common Stock	0.00%	0.00%	0.00%	0.00%	0.00%	0.00%	0.00%	0.00%	0.00%	0.00%	0.00%	0.00%

Financials

SKWD vs. PGR - Profitability Comparison

The chart below illustrates the profitability comparison between Skyward Specialty Insurance Group Inc. Common Stock and The Progressive Corporation over time, highlighting three key metrics: Gross Profit Margin, Operating Margin, and Net Profit Margin.

SKWD - Gross Margin

Gross margin is calculated as gross profit divided by revenue. For the three months ending on Jun 2026, Skyward Specialty Insurance Group Inc. Common Stock reported a gross profit of 0.00 and revenue of 475.87M. Therefore, the gross margin over that period was 0.0%.

PGR - Gross Margin

Gross margin is calculated as gross profit divided by revenue. For the three months ending on Jun 2026, The Progressive Corporation reported a gross profit of 6.66B and revenue of 22.74B. Therefore, the gross margin over that period was 29.3%.

SKWD - Operating Margin

Operating margin is calculated as operating income divided by revenue. For the three months ending on Jun 2026, Skyward Specialty Insurance Group Inc. Common Stock reported an operating income of 0.00 and revenue of 475.87M, resulting in an operating margin of 0.0%.

PGR - Operating Margin

Operating margin is calculated as operating income divided by revenue. For the three months ending on Jun 2026, The Progressive Corporation reported an operating income of 3.68B and revenue of 22.74B, resulting in an operating margin of 16.2%.

SKWD - Net Margin

Net margin is calculated as net income divided by revenue. For the three months ending on Jun 2026, Skyward Specialty Insurance Group Inc. Common Stock reported a net income of 49.73M and revenue of 475.87M, resulting in a net margin of 10.5%.

PGR - Net Margin

Net margin is calculated as net income divided by revenue. For the three months ending on Jun 2026, The Progressive Corporation reported a net income of 2.95B and revenue of 22.74B, resulting in a net margin of 13.0%.

Frequently Asked Questions

Can I hold both SKWD and PGR in my portfolio?

SKWD and PGR have a correlation of 0.34, meaning they provide meaningful diversification benefit when combined. Depending on your allocation goals, holding both could reduce overall portfolio risk.

Which is riskier, SKWD or PGR?

SKWD has higher volatility (10.00%) compared to PGR (5.82%). In terms of maximum drawdown, SKWD dropped -36.52% vs PGR's -71.06%.

Which has better risk-adjusted returns?

SKWD currently has the higher Sharpe Ratio (-1.01 vs -1.28), meaning it's delivered slightly more return per unit of risk over the trailing 12 months. However, this ranking shifts over time - use the Risk/Return Score above for a more comprehensive view that combines Sharpe, Sortino, and other measures used by quantitative funds.