Which has the lower trailing P/E, SKWD or UPST?

SKWD has the lower trailing P/E: SKWD trades at 13.17 and UPST at 46.66. P/E is one valuation measure and does not by itself establish which business is cheaper.

Which has grown faster, SKWD or UPST?

Over the past five years, SKWD grew revenue faster — SKWD at a 27.90% CAGR versus UPST at 22.79%.

Is SKWD or UPST more profitable?

SKWD runs the higher net margin — SKWD at 11.45% versus UPST at 4.69%.

Skyward Specialty Insurance Group, Inc. (SKWD) vs Upstart Holdings, Inc. (UPST)

A side-by-side comparison of Skyward Specialty Insurance Group, Inc. and Upstart Holdings, Inc. across valuation, profitability, dividends, and growth — built entirely from reported fundamentals, as of October 6, 2026. Differences are shown without an overall score or investment verdict.

SKWD

Skyward Specialty Insurance Group, Inc.

$2.29B

$56.49Financial ServicesDelayed quote: Oct 6, 2026, 4:00 PM EDT

UPST

Upstart Holdings, Inc.

$2.28B

$23.86Financial ServicesDelayed quote: Oct 6, 2026, 4:00 PM EDT

Total return — SKWD vs UPST

growth of $100 · dividends reinvested · last 4y

SKWD +189.0% (+30.4%/yr)UPST +43.3% (+9.4%/yr)SKWD compounded faster over this window

SKWD UPST

SKWD vs UPST: by the numbers

•SKWD is the larger company ($2.29B vs $2.28B market cap).
•SKWD trades at the lower trailing earnings multiple (13.17 vs 46.66 P/E), one valuation lens rather than an overall verdict.
•SKWD converts more revenue to profit (11.45% vs 4.69% net margin).
•SKWD grew revenue faster over the past five years (27.90% vs 22.79% CAGR).

Metrics side by side

Valuation

Metric	SKWD	UPST
P/E ratio	13.17	46.66
Forward P/E	11.24	35.20
PEG ratio	N/A	3.25
P/S ratio	1.40	1.78
P/B ratio	1.81	2.86

Profitability

Metric	SKWD	UPST
Operating margin	14.68%	4.80%
Net margin	11.45%	4.69%
ROE	14.82%	7.57%

Skyward Specialty Insurance Group, Inc.: Gross margin is not shown for a lender or insurer: its revenue is interest, premiums and fees rather than the sale of goods, so there is no cost of goods sold to measure it against.

Upstart Holdings, Inc.: Gross margin is not shown for a lender or insurer: its revenue is interest, premiums and fees rather than the sale of goods, so there is no cost of goods sold to measure it against.

Growth (annualized)

Metric	SKWD	UPST
Revenue CAGR (5Y)	27.90%	22.79%
EPS CAGR (5Y)	N/A	15.71%
Total return CAGR (5Y)	N/A	-39.34%

Frequently asked

Which has the lower trailing P/E, SKWD or UPST?: SKWD has the lower trailing P/E: SKWD trades at 13.17 and UPST at 46.66. P/E is one valuation measure and does not by itself establish which business is cheaper.
Which has grown faster, SKWD or UPST?: Over the past five years, SKWD grew revenue faster — SKWD at a 27.90% CAGR versus UPST at 22.79%.
Is SKWD or UPST more profitable?: SKWD runs the higher net margin — SKWD at 11.45% versus UPST at 4.69%.

Go deeper

Full SKWD analysis Full UPST analysis Interactive comparison tool

Dig into the metrics

Skyward Specialty Insurance P/E ratio Upstart P/E ratio Skyward Specialty Insurance ROE Upstart ROE Skyward Specialty Insurance operating margin Upstart operating margin Skyward Specialty Insurance revenue growth Upstart revenue growth

Skyward Specialty Insurance & Upstart appear in these rankings

Fastest Revenue Growth Stocks Lowest P/E Ratio Stocks

Figures are sourced from reported fundamentals and the latest end-of-day price. This comparison is informational only and is not investment advice. Past performance does not predict future results. See our methodology. Compiled by TGMCharts Research · data verified October 6, 2026.