Skyward Specialty Insurance Group

SKWD on Nasdaq. Skyward Specialty sells commercial insurance to businesses that standard insurers often do not cover. Market value $2.5bn.

Watch this stockFree. We tell you when something changes.

Price checks use the past 12 months to June 2026. Some use the latest annual report instead, as marked. Quality checks use five annual reports, the latest for the year to December 2025.

We can't read total debt from the filing, so debt is left out.

Should I look at this?

Worth a closer look

Read what could go wrong

This is not advice. Check the numbers below.

Compare with another stock

Return on equity
five annual reports to December 2025
16.3%five-year median

Yearly profit per dollar of owners' money: 16 cents. Above 10 is good.

Price to book
quarterly report to June 2026
2.0×

What you pay for each dollar of net assets: $1.98.

Earnings yield
past 12 months to June 2026
7.5%

Profit per $100 you pay: $7.49.

Quality score: 100 of 100. Price score: 72 of 100. Our list needs 70 on quality and 60 on price.

$56.49 a share, 39% above its 1-year low

Over the past year the price has ranged from $40.60 to $65.69.

Pays no dividend

Prices from Tuesday’s close (6 October).

Five years of cash, in billions

n/a
n/a
n/a
n/a
2022202320242025
Revenue
$642m$886m$1.2bn$1.4bn
Operating margin
n/an/an/an/a
Debt to equity
n/an/an/an/a
Shares outstanding
0.04bn0.04bn0.04bn0.04bn

Health checks

  • Free cash flow positiveDoesn't apply to banks and insurers
  • Accounting checksDoesn't apply to banks and insurers
  • DebtDoesn't apply to banks and insurers
  • Revenue growth, five yearsStrong, 30.1% a year
  • Buying back its own sharesNo, 18% more shares since 2022

The quarter to June 2026

How the business did, compared with the same quarter a year earlier.

  • Sales: $490 million last quarter, up 53% on a year ago.
  • Profit: $49 million, up 26% on a year ago.
  • Spare cash over the past 12 months: $402 million, up from $372 million.
  • 9% more shares than a year ago. Each share owns a bit less of the company.
  • Sales grew on a year ago in each of the last 4 quarters.
Sales by quarter
Sales by quarter
Quarter toAmount
September 2024$301m
December 2024$304m
March 2025$329m
June 2025$320m
September 2025$383m
December 2025$386m
March 2026$476m
June 2026$490m
Profit by quarter
Profit by quarter
Quarter toAmount
September 2024$37m
December 2024$14m
March 2025$42m
June 2025$39m
September 2025$46m
December 2025$43m
March 2026$50m
June 2026$49m

From the company's quarterly reports to the SEC.

Dates

Next results (estimated)
n/a
Last annual report (10-K)
2 March 2026
Next quarterly (estimated, 10-Q)
6 November 2026

Who owns it

1 long-term investor we follow owns it, unchanged from 1 last quarter. 244 funds in all.

Jun '25
Dec '25
Jun '26
Largest holders overall

From 13F filings for the quarter ended 30 June 2026.

Big holders and activists

3 investors own more than 5%.

From Schedule 13D and 13G filings: anyone owning more than 5% must file one.

What insiders did

In the last 12 months, 4 insiders bought $2m of shares on the open market. 3 sold $969,099, $503,866 of it under preset trading plans.

  • Schmitt Thomas N
    CPO, Skyward Group
    Sold
    Date
    12 June 2026
    Shares
    8,397
    Price
    $51.32
    Value
    $430,934
  • Kuczinski Anthony J
    Director
    Bought
    Date
    21 May 2026
    Shares
    2,000
    Price
    $47.10
    Value
    $94,200
  • Ashe Gena L
    Director
    Sold
    Date
    11 May 2026
    Shares
    740
    Price
    $46.35
    Value
    $34,299
  • Kuczinski Anthony J
    Director
    Bought
    Date
    3 March 2026
    Shares
    1,000
    Price
    $48.13
    Value
    $48,130
  • Kuczinski Anthony J
    Director
    Bought
    Date
    2 March 2026
    Shares
    2,000
    Price
    $48.79
    Value
    $97,580
  • Peirce Christopher Locke
    Director
    Bought
    Date
    2 March 2026
    Shares
    3,200
    Price
    $47.30
    Value
    $151,360
  • Kuczinski Anthony J
    Director
    Bought
    Date
    27 February 2026
    Shares
    2,000
    Price
    $46.88
    Value
    $93,760
  • McHarg Taryn Leonie
    CFO - Apollo
    Bought
    Date
    27 February 2026
    Shares
    200
    Price
    $46.60
    Value
    $9,320
  • Robinson Andrew S
    Chairman & CEO, Skyward Group, Director
    Bought
    Date
    27 February 2026
    Shares
    22,100
    Price
    $46.76
    Value
    $1m
  • Schmitt Thomas N
    CPO, Skyward Group
    Sold
    under a preset trading plan
    Date
    9 February 2026
    Shares
    2,616
    Price
    $43.49
    Value
    $113,770

From Form 4 filings: insiders must report trades in their own company's shares within two days.

What could go wrong

Cheap for a reason is the question the numbers cannot answer.

Whether the price already reflects the risks is what the deep dive is for.

What changed in the risks this year

Companies must list what could hurt them each year. These are the parts that changed since last year’s report.

  • The acquisition and integration of Apollo may adversely affect our business, financial condition and results of operations.

    Could happen
    • Financial and Accounting Risks: The acquisition may result in significant changes to our financial statements, including the recognition of goodwill and other intangible assets, which could be subject to future impairment. In addition, the acquired business may have undisclosed liabilities or risks that could adversely affect our financial results. Furthermore, as Apollo’s financial statements are currently prepared under U.K. GAAP, which will need to be converted to U.S. GAAP, which may require adjustments to accounting policies, estimates, and disclosures, potentially impacting reported balances and comparability with prior periods.
    Read more
  • Our use of derivatives to mitigate exposure to market price volatility may subject us to risks such as hedge ineffectiveness, basis risk, collateral and margin call liquidity pressures, and valuation uncertainty inherent in futures and options markets, any of which could adversely affect our financial condition.

    Could happen
    Our use of derivatives to mitigate exposure to market price volatility subjects us to risks that could adversely affect our financial condition and results of operations. These risks include hedge ineffectiveness due to imperfect correlation between derivatives and the underlying exposures, a recognized limitation in commodity market hedge theory; basis risk, where futures prices do not move in line with cash market prices relevant to our business; and liquidity pressures arising from margin call or collateral requirements associated with futures positions during adverse market movements. Additionally, reliance on market based models introduces valuation uncertainty that may cause hedges to perform differently than expected. Together, these factors may prevent our hedging strategies from effectively reducing volatility and could materially adversely impact our financial results.
    Read more
  • • our use of derivatives to mitigate exposure to market price volatility may subject us to risks such as hedge ineffectiveness, basis risk,…

    Could happen
    • our use of derivatives to mitigate exposure to market price volatility may subject us to risks such as hedge ineffectiveness, basis risk, collateral and margin call liquidity pressures, and valuation uncertainty inherent in futures and options markets, any of which could adversely affect our financial condition; and • the integration of Apollo may present unforeseen challenges, including potential difficulties in integrating technology systems, business processes, and risk management frameworks, which could result in operational disruptions, increased costs, or delays in realizing anticipated strategic benefits from the acquisition.
    Read more
  • Artificial intelligence is an evolving and rapidly growing technology which may impact our business and operations.

    Could happen
    The rapid growth and development of artificial intelligence and machine learning may alter the competitive landscape in which we operate. Our employees utilize artificial intelligence for risk selection, pricing and claims handling to aid in their effectiveness and efficiency and we continue to research and implement artificial intelligence-based solutions in an effort to improve our business. Notwithstanding this, our competitive position may be harmed if competitors are able to leverage artificial intelligence solutions more quickly or more effectively. In addition, while we do not rely solely on information and analysis production through artificial intelligence in our decision making, if the content, analyses or recommendations that artificial intelligence applications assist in producing are, or are alleged to be, deficient, inaccurate or biased, such as due to limitations in algorithms, insufficient or biased base data or flawed training methodologies, our business, financial condition, results of operations and reputation may be adversely affected. Further, as artificial intelligence technology and products are continuously evolving, we may incur costs to adopt and deploy technologies that could become obsolete earlier than expected. There can be no assurance that we will realize the desired or anticipated benefits from artificial intelligence.
    Read more
  • The acquisition and integration of Apollo may adversely affect our business, financial condition and results of operations.

    Could happen
    • Integration Risks: The successful integration of Apollo’s operations, systems, technology platforms, and personnel with our own is subject to significant challenges. Difficulties in integrating Apollo may result in the diversion of management’s attention and resources, disruption of ongoing business, and the incurrence of unexpected costs or delays.
    Read more

Read it in the annual report

The deep dive

Everything above is arithmetic on public filings. The deep dive reads the last ten years of annual reports, the proxy statements, and the earnings calls, then argues the case the way Buffett, Klarman, and Hohn would, and checks every claim against the source.

  • What the business is worth, as a range, and the margin of safety at today’s price
  • Prices to start buying, buy, and buy hard
  • The three things that would make this a mistake
  • Every number footnoted to the filing it came from

It just passed both our tests. The deep dive checks what the numbers can't.

Create a free account to run it

Your first deep dive is free.

What a finished deep dive looks like

Not advice. Numbers on this page come from SEC filings and are updated each night; prices are updated again after the US market closes. The five-year figures are rounded.