Skyward Specialty Insurance Group, Inc. (SKWD): fair value, margin of safety and Wheel Score

Is SKWD undervalued?

At 59.35 (close of 16 Oct 2026), SKWD trades 65% below the GLS average fair value of 170.73. That average comes from 7 models run on the latest filings, and 4 of them land above the current price. Margins of safety over 30% are the exception rather than the rule across the ~7,400 stocks we value each night, so the number earns Skyward Specialty Insurance Group, Inc. the full Value points in the Wheel Score - and a closer look at what the market is pricing in.

There is a wide gap between Lynch (47.72) and Payback Time (395.70). When the models are this far apart the "fair value" is really a range, and the margin of safety above should be read with that range in mind.

The nightly engine files SKWD under High Growth: revenue and earnings growing fast enough that the growth-based models carry the valuation.

Nine valuation models for SKWD

Each model turns the latest filed numbers into a value per share; the GLS fair value is the simple average of the ones that produce a positive number. The last two rows are shown for reference and never enter the average. The Quote page lets you switch any model off and add your own margin of safety.

Quality and financial health

Skyward Specialty Insurance Group, Inc. scores 5 of 9 on the Piotroski F-score: a middling result that falls one point short of the Sunday Scan's "6 or more" rule. Some of the nine tests on profitability, leverage and efficiency are failed, so the accounts are worth a look before selling a put on the name. A GLS Moat score of 7.7/10 puts SKWD among the more durable businesses we track: over ten years the metrics the score watches (revenue, EPS, book value, margins, cash flow, ROIC) have mostly moved the right way, year after year.

Returns on capital are high - ROIC 15.1%, ROE 16.8%, ROA 3.5% - with debt at 0.12 times equity and a free-cash-flow yield of 15.3%.

Skyward Specialty Insurance Group, Inc. pays no dividend, so the DDM model does not apply and a covered-call holder earns only the premium and any price gain.

Institutional ownership scores 10/10, insider activity 7/10 and Congressional trading 10/10 on the GLS smart-money scales; the last recorded Congressional buy was on 16 Jul 2026.

Wheel Score 80: Prime

With a Wheel Score of 80, Skyward Specialty Insurance Group, Inc. sits in the Prime band - price, quality and premium all line up for the wheel strategy. The parts: Value 25/25, Health 11/20, Moat 12/15, Premium 20/20, Stability 13/20. A high score is a ranking, not a signal: it says nothing about timing, the earnings date or your position size.

Implied volatility is 40% on the near-the-money contracts 20-60 days out - inside the 35-60% range the Wheel Score pays full marks for: enough premium to be worth selling, not so much that the risk is unpaid. Chain open interest is thin - 1,399 contracts across every expiry - so fills at a fair price are not guaranteed; a 30-45-day put may not exist at a usable strike.

Volume runs at 305k shares a day on a market cap of $2.6B, with a beta of 0.32 - a low beta, so day-to-day moves are smaller than the market's; the Stability part of the Wheel Score gives that 13 of 20.

The Wheel Score ranks ~7,400 US stocks for selling cash-secured puts and covered calls; it is updated nightly and is not a recommendation. The walkthrough lesson shows how the score fits into a trade, start to finish.

Upcoming events

The next earnings report is due on 4 Nov 2026 (after the close), 19 days away; a 30-45-day put sold today would expire after it, which is worth weighing against the premium.

Earnings, dividend, IPO, split and economic calendars for the whole market, filterable to your watchlists.

Similar stocks in Insurance - Property & Casualty

The 12 companies below are the closest to Skyward Specialty Insurance Group, Inc. by market cap within the Insurance - Property & Casualty industry, each with its own fact sheet; the Compare page puts up to eight of them side by side.

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