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No insider purchase over the last 90 days. The latest was filed 04 Mar 2026.
Skyward Specialty Insurance Group, Inc.: what insiders have been doing
Every trade that managers of Skyward Specialty Insurance Group, Inc. disclose to SEC (Form 4) is tracked on this page. The company sits in the Banks sector. In the past year (18 October 2025 to 18 October 2026), 39 filings came from 15 insiders.
The record shows 4 purchases on the open market worth €639k, made by 4 insiders, against 7 sales worth €406k by 3 insiders. The net balance comes to €233k on the buying side. Open-market purchases are the filings investors watch most closely, because the insider pays for the shares out of pocket. Among those who bought: 2 senior executives, 1 finance chief and 1 chief executive. Biggest ticket of the year: €427k, bought by Robinson Andrew S and made public on 27 February 2026.
For context, the typical company on the same exchange (median of 5,816 companies) published 19 filings over the same period, against 39 filings here. Looking back to 2023, when coverage begins, insiders filed 6 purchases and 37 sales. The 10-K for the year ended 31 December 2025 shows 1.42 bn USD of revenue and 170.0 m USD of net income.
In all, 3 purchases were made within 30 days of a purchase by another insider of the company. Purchases made close together by different insiders form what is called a cluster. The last purchase on record was published on 4 March 2026, which is 228 days ago. Between a trade and the moment it shows up on SEC (Form 4), the median delay is 2 days. Section 16 rules allow two business days to file each Form 4. A sale on its own says little: insiders also sell to pay tax, fund a purchase or diversify.
Elsewhere in the same sector, our signals recently picked up insider purchases at First Guaranty Bancshares, Inc. and BCB Bancorp Inc. Every figure here comes from the filings published by SEC (Form 4) and describes the past, not future prices; it is not investment advice.
Insider Decl.
125
Thresholds
n/a
Buy Volume
€675,285
6 ops. · all time
Sell Volume
€291M
37 ops. · all time
Who traded when
BuySaleAndrew S. Robinson1 buy3 sales
Gena L. Ashe4 sales
Thomas N. Schmitt4 sales
Hays James Charles3 sales
Hill Kirby3 sales
Sandip A. Kapadia3 sales
+8 other insiders
Since the insiders bought
- -13.1%Entry US$49.17 · Close at T+90 US$42.73
- -9.4%Entry US$48.65 · Close at T+90 US$44.10
- -9.4%Entry US$48.65 · Close at T+90 US$44.10
Entry is the close on the day after publication, the first price a reader could act on. Prices in the listing currency. Past moves are not a forecast.
Analyst consensus: bullish or bearish?
Analysts rate Skyward Specialty Insurance Group, Inc. Buy (bullish), based on 11 analysts. Average price target: US$70.73.
This score ranks the purchase within its own market. A position size is suggested only on the venues of the backtested strategy universe; elsewhere, signals stay on watch. Not investment advice.
Fundamental score
Ranked 1,773 of 24,148 companies
76.4
score / 100
Value73
Quality79
FCF yld15%
Earn yld6.3%
EV/EBITDA9.6x
ROE17%
Gross mgn·
Net mgn12%
Debt/EBITDA0.4x
Pillars2/3
Transparent value + quality ranking, distinct from the insider signal.
Financial data
as of FY 2025FY ended December 2025 · cache
US$61.23
Analyst consensus
11 analystsBuy
US$56.00Target US$70.73(+16%)US$80.00
Income statement
RevenueUS$1.4B
EBITDAUS$296.1M21% margin
Net incomeUS$170M10.8% margin
Valuation
PER (trailing)14.2x
PER (forward)11.1x
P/Book2.1x
Beta0.36
Balance sheet & cash
Market capUS$2.7B
Total debtUS$120M
Free Cash FlowUS$400.6M
Debt / Equity34%
Profitability & ownership
ROE17.3%
ROA3.1%
% insiders8.2%
% institutions92.8%
Last declaration on 12 June 2026
Declarations125 total
88 shares@ US$47.3833100.0% of flowCommon StockSEC144:0001628280-26-042764
8,397 shares@ US$51.2924100.0% of flowCommon StockSEC144:0001628280-26-042970
500 shares@ US$46.350.0010% mcap25.9% of flowCommon StockSEC:0001669943-26-000006:3
100 shares@ US$46.350.0002% mcap5.2% of flowCommon StockSEC:0001669943-26-000006:1
140 shares@ US$46.350.0003% mcap7.2% of flowCommon StockSEC:0001669943-26-000006:2
1,797 sharesCommon StockSEC:0001669943-26-000006:0
2,000 shares@ US$46.875168.7% of flowCommon StockSEC:0001976607-26-000002:0
Canonical exit: 28 May 2026 (T+90)
100 shares@ US$46.711.2% of flowCommon StockSEC:0002102589-26-000008:0
Canonical exit: 28 May 2026 (T+90)
3,200 shares@ US$47.30100.0% of flowCommon StockSEC:0002106014-26-000004:0
Canonical exit: 31 May 2026 (T+90)
17,575 shares0Common StockSEC:0001415833-26-000008:0
4,198 shares0Common StockSEC:0001936023-26-000006:0
3,318 shares0Common StockSEC:0001936008-26-000006:0
10,821 shares@ US$46.579.8% of flowCommon StockSEC:0001415833-26-000010:0
Canonical exit: 28 May 2026 (T+90)
2,343 shares0Common StockSEC:0001937549-26-000006:0
2,929 shares0Common StockSEC:0001937316-26-000008:0
2,343 shares0Common StockSEC:0001937132-26-000006:0
4,392 shares0Common StockSEC:0001211319-26-000006:0
2,616 shares@ US$43.491621.7% of flowCommon StockSEC:0001937316-26-000006:0
5,000 shares0Common StockSEC:0001937549-26-000004:0
5,000 shares0Common StockSEC:0001937316-26-000004:0
5,000 shares0Common StockSEC:0001937132-26-000004:0
50,000 shares0Common StockSEC:0001415833-26-000006:0
6,665 shares0Common StockSEC:0001936023-26-000004:0
5,000 shares0Common StockSEC:0001936008-26-000004:0
6,665 shares0Common StockSEC:0001211319-26-000004:0
25 of 125 declarations
About Skyward Specialty Insurance Group, Inc.
Skyward Specialty Insurance Group, Inc. (ticker: SKWD) is a U.S.-listed specialty insurer traded on the Nasdaq, not the NYSE, placing it in the American small/mid-cap growth segment. The company is a Delaware-incorporated insurance holding company founded in 2006 and headquartered in Houston, Texas. Its positioning is built around a “rule our niche” strategy: rather than competing broadly in commoditized property and casualty insurance, Skyward focuses on technically complex, under-served specialty markets where underwriting expertise and speed of execution matter most. The company provides commercial P&C solutions on both admitted and non-admitted bases.([skywardinsurance.com](https://skywardinsurance.com/about/?utm_source=openai))
Operationally, Skyward Specialty is organized into nine underwriting divisions: Accident & Health, Agriculture & Credit (Re)insurance, Captives, Construction & Energy Solutions, Global Property, Professional Lines, Specialty Programs, Surety, and Transactional E&S. This structure gives the group broad specialty reach while keeping its portfolio tightly focused on niche risks. A key part of its competitive advantage is the use of proprietary analytics and workflow tools such as SkyBI and SkyVantage, which the company says help underwriters and claims professionals react faster to market trends, improve risk selection, and maintain disciplined underwriting.([skywardinsurance.com](https://skywardinsurance.com/about/?utm_source=openai))
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The company’s insurance platform is supported by operating subsidiaries including Great Midwest Insurance Company, Houston Specialty Insurance Company, Imperium Insurance Company, and Oklahoma Specialty Insurance Company. Geographically, Skyward’s core business has been centered in the United States, but the business took a meaningful strategic step in 2026 when it completed its acquisition of Apollo and introduced Skyward Group as the new holding-company brand for its U.S. and Lloyd’s businesses. That move expands the group’s footprint beyond the domestic market and strengthens its access to global specialty property and casualty opportunities.([investors.skywardinsurance.com](https://investors.skywardinsurance.com/news-releases/news-release-details/skyward-specialty-introduces-skyward-group-new-holding-company/?utm_source=openai))
Skyward has continued to broaden its specialty product set with targeted launches in recent periods, including life sciences liability, aviation, mortgage reinsurance, power generation, renewable energy, and enhanced E&S property capabilities. These actions are consistent with a company that is intentionally building depth in profitable specialist niches rather than pursuing scale for its own sake. The product strategy also suggests a higher-value underwriting mix, where expertise, relationships with brokers, and tailored coverage design can support margin resilience.([investors.skywardinsurance.com](https://investors.skywardinsurance.com/news-releases/news-release-details/skyward-specialty-launches-new-life-sciences-liability-insurance?utm_source=openai))
The most important recent corporate development is the acquisition of Apollo, announced in September 2025 and closed on January 1, 2026, followed by the January 2026 rollout of the Skyward Group brand. Management framed the transaction as a way to amplify its specialty strategy, add new niche capabilities, and bring in Apollo’s Lloyd’s platform and technology strengths. For investors, SKWD stands out as a Nasdaq-listed U.S. specialty insurer with a differentiated underwriting model, a growing product suite, and a recent strategic step toward a more global specialty platform.([skywardinsurance.com](https://skywardinsurance.com/press-releases/skyward-specialty-insurance-group-to-acquire-apollo-group-holdings-limited-amplifying-rule-our-niche-strategy/?utm_source=openai))
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