Skyward Specialty Insurance Group, Inc.
SKWD · Fire, Marine & Casualty Insurance · 40.5M shares · +6%/yr ↑ shares · EDGAR filings ↗
Reference price $51.32 · est. market cap ~$2.1B — last insider sale, 2026-06-12 (estimated from the dated SEC Form 4 price × shares outstanding — not a live quote)
Grade
B77Fast-growing, A-rated specialty (E&S) insurer with high ROE and top-decile premium growth across a diversified niche book.
Strengths
- Strong returns and growth: ROE 16.8%, revenue up 23.4% (97th pct), net income up 43%, OCF margin 78th pct
- Diversified nine-division specialty platform with A.M. Best 'A' rating; Apollo/Lloyd's acquisition extends the franchise
Risks
- Reserve-adequacy, reinsurance-recovery and underwriting-cycle risks inherent to specialty P&C
- Integration risk from the Apollo acquisition; ROA only mid-pack (50th pct)
Notable findings
- Exec changeRecent 8-K item 5.02 8-K ↗
- Strong balance sheetStrong balance sheet — $169M cash & investments
- Insider buyingInsider buying — 11 open-market buy(s) by 4 insider(s) (cluster of 4 insiders, ~$2M, last 6mo) Form 4 ↗
- Insider sellingInsider selling — 5 open-market sale(s) by 2 insider(s) (cluster of 2 insiders, ~$579,036, last 6mo) Form 4 ↗
Quarterly revenue
Last 4 quarters · from SEC filings.
Key metrics
Net margin
12.0%
Return on equity
16.8%
Return on assets
3.5%
Revenue growth (QoQ)
23.4%
Net-income growth
43.1%
Free cash flow
$403M
Tangible book value
$922M
Cash & investments
$169M
Stock comp / revenue
0.8%
Insider transactions · last 18 months
| Date | Insider | Type | Shares | Price |
|---|---|---|---|---|
| 2026-06-12 | Schmitt Thomas N | Sell | 8.4K | $51.32 |
| 2026-05-21 | Kuczinski Anthony J | Buy | 1.0K | $47.20 |
| 2026-05-21 | Kuczinski Anthony J | Buy | 200 | $47.00 |
| 2026-05-21 | Kuczinski Anthony J | Buy | 800 | $47.00 |
| 2026-05-11 | Ashe Gena L | Sell | 500 | $46.35 |
| 2026-05-11 | Ashe Gena L | Option exercise | 1.8K | — |
| 2026-05-11 | Ashe Gena L | Sell | 100 | $46.35 |
| 2026-05-11 | Ashe Gena L | Sell | 140 | $46.35 |
| 2026-05-07 | Kuczinski Anthony J | Option exercise | 1.8K | — |
| 2026-05-06 | Burkhart John A III | Option exercise | 4.8K | — |
| 2026-05-06 | Bodnar Dan PK | Option exercise | 2.7K | — |
| 2026-05-06 | Bodnar Dan PK | Tax withheld | 1.0K | $43.68 |
| 2026-05-06 | Schmitt Thomas N | Option exercise | 3.4K | — |
| 2026-05-06 | Schmitt Thomas N | Tax withheld | 1.3K | $43.68 |
| 2026-05-06 | Kapadia Sandip A | Option exercise | 2.7K | — |
| 2026-05-06 | Kapadia Sandip A | Tax withheld | 1.4K | $43.68 |
| 2026-05-06 | Burkhart John A III | Tax withheld | 1.9K | $43.68 |
| 2026-05-06 | Duffy Sean W | Option exercise | 3.8K | — |
| 2026-05-06 | Duffy Sean W | Tax withheld | 1.7K | $43.68 |
| 2026-05-06 | Robinson Andrew S | Option exercise | 20K | — |
| 2026-05-06 | Robinson Andrew S | Tax withheld | 7.9K | $43.68 |
| 2026-05-06 | HAUSHILL MARK W | Option exercise | 5.0K | — |
| 2026-05-06 | HAUSHILL MARK W | Tax withheld | 2.0K | $43.68 |
| 2026-05-05 | Hays James Charles | Option exercise | 1.8K | — |
| 2026-05-05 | Creager Robert E. | Option exercise | 1.8K | — |
| 2026-03-03 | Kuczinski Anthony J | Buy | 1.0K | $48.13 |
| 2026-03-02 | Kuczinski Anthony J | Buy | 2.0K | $48.79 |
| 2026-03-02 | Peirce Christopher Locke | Buy | 3.2K | $47.30 |
| 2026-02-27 | McHarg Taryn Leonie | Buy | 100 | $46.49 |
| 2026-02-27 | Robinson Andrew S | Buy | 11K | $46.57 |
| 2026-02-27 | Kuczinski Anthony J | Buy | 2.0K | $46.88 |
| 2026-02-27 | McHarg Taryn Leonie | Buy | 100 | $46.71 |
| 2026-02-27 | Robinson Andrew S | Buy | 11K | $46.94 |
| 2026-02-26 | HAUSHILL MARK W | Tax withheld | 1.4K | $45.89 |
| 2026-02-26 | Bodnar Dan PK | Tax withheld | 876 | $45.89 |
| 2026-02-26 | Schmitt Thomas N | Tax withheld | 1.2K | $45.89 |
| 2026-02-26 | Kapadia Sandip A | Tax withheld | 847 | $45.89 |
| 2026-02-26 | Burkhart John A III | Tax withheld | 1.7K | $45.89 |
| 2026-02-26 | Duffy Sean W | Tax withheld | 1.4K | $45.89 |
| 2026-02-26 | Robinson Andrew S | Tax withheld | 6.9K | $45.89 |
| 2026-02-25 | Duffy Sean W | Option exercise | 3.3K | — |
| 2026-02-25 | Robinson Andrew S | Option exercise | 18K | — |
| 2026-02-25 | Schmitt Thomas N | Option exercise | 2.9K | — |
| 2026-02-25 | HAUSHILL MARK W | Option exercise | 4.4K | — |
| 2026-02-25 | Kapadia Sandip A | Option exercise | 2.3K | — |
| 2026-02-25 | Bodnar Dan PK | Option exercise | 2.3K | — |
| 2026-02-25 | Burkhart John A III | Option exercise | 4.2K | — |
| 2026-02-09 | Schmitt Thomas N | Sell | 2.6K | $43.49 |
| 2026-01-12 | Schmitt Thomas N | Option exercise | 5.0K | — |
| 2026-01-12 | Schmitt Thomas N | Tax withheld | 2.1K | $46.10 |
| 2026-01-12 | Schmitt Thomas N | Option exercise | 5.0K | — |
| 2026-01-12 | Schmitt Thomas N | Tax withheld | 2.0K | $46.10 |
| 2026-01-12 | Kapadia Sandip A | Option exercise | 5.0K | — |
| 2026-01-12 | Kapadia Sandip A | Tax withheld | 2.0K | $46.10 |
| 2026-01-12 | Kapadia Sandip A | Option exercise | 5.0K | — |
| 2026-01-12 | Kapadia Sandip A | Tax withheld | 1.8K | $46.10 |
| 2026-01-12 | Burkhart John A III | Option exercise | 6.7K | — |
| 2026-01-12 | Burkhart John A III | Tax withheld | 2.8K | $46.10 |
| 2026-01-12 | Burkhart John A III | Option exercise | 6.7K | — |
| 2026-01-12 | Burkhart John A III | Tax withheld | 2.6K | $46.10 |
| 2026-01-12 | Duffy Sean W | Option exercise | 5.0K | — |
| 2026-01-12 | Duffy Sean W | Tax withheld | 2.3K | $46.10 |
| 2026-01-12 | Duffy Sean W | Option exercise | 5.0K | — |
| 2026-01-12 | Duffy Sean W | Tax withheld | 2.1K | $46.10 |
| 2026-01-12 | Robinson Andrew S | Option exercise | 50K | — |
| 2026-01-12 | Robinson Andrew S | Tax withheld | 20K | $46.10 |
| 2026-01-12 | Robinson Andrew S | Option exercise | 50K | — |
| 2026-01-12 | Robinson Andrew S | Tax withheld | 20K | $46.10 |
| 2026-01-12 | HAUSHILL MARK W | Option exercise | 6.7K | — |
| 2026-01-12 | HAUSHILL MARK W | Tax withheld | 2.8K | $46.10 |
| 2026-01-12 | HAUSHILL MARK W | Option exercise | 6.7K | — |
| 2026-01-12 | HAUSHILL MARK W | Tax withheld | 2.6K | $46.10 |
| 2026-01-12 | Bodnar Dan PK | Option exercise | 5.0K | — |
| 2026-01-12 | Bodnar Dan PK | Tax withheld | 2.0K | $46.10 |
| 2026-01-12 | Bodnar Dan PK | Option exercise | 5.0K | — |
| 2026-01-12 | Bodnar Dan PK | Tax withheld | 1.9K | $46.10 |
| 2026-01-01 | Duffy Sean W | Option exercise | 2.9K | — |
| 2026-01-01 | McHarg Taryn Leonie | Grant | 7.8K | $50.00 |
| 2026-01-01 | Slaughter James Richard | Grant | 55K | $50.00 |
| 2026-01-01 | Slaughter James Richard | Grant | 13K | $50.00 |
| 2026-01-01 | Ibeson David Christopher Ben | Grant | 267K | $50.00 |
| 2026-01-01 | Ibeson David Christopher Ben | Grant | 80K | $50.00 |
| 2026-01-01 | Bodnar Dan PK | Option exercise | 2.0K | — |
| 2026-01-01 | Bodnar Dan PK | Tax withheld | 765 | $51.11 |
| 2026-01-01 | Schmitt Thomas N | Option exercise | 2.5K | — |
| 2026-01-01 | Schmitt Thomas N | Tax withheld | 1.0K | $51.11 |
| 2026-01-01 | Kapadia Sandip A | Option exercise | 2.0K | — |
| 2026-01-01 | Kapadia Sandip A | Tax withheld | 741 | $51.11 |
| 2026-01-01 | Burkhart John A III | Option exercise | 3.6K | — |
| 2026-01-01 | Burkhart John A III | Tax withheld | 1.4K | $51.11 |
| 2026-01-01 | Duffy Sean W | Tax withheld | 1.3K | $51.11 |
| 2026-01-01 | Hays James Charles | Grant | 144K | $50.00 |
| 2026-01-01 | Robinson Andrew S | Option exercise | 15K | — |
| 2026-01-01 | Robinson Andrew S | Tax withheld | 6.0K | $51.11 |
| 2026-01-01 | HAUSHILL MARK W | Option exercise | 3.8K | — |
| 2026-01-01 | HAUSHILL MARK W | Tax withheld | 1.5K | $51.11 |
| 2025-12-18 | Kapadia Sandip A | Sell | 5.0K | $50.01 |
| 2025-12-12 | Kapadia Sandip A | Sell | 1.2K | $50.01 |
| 2025-12-12 | Kapadia Sandip A | Sell | 1.5K | $50.03 |
| 2025-12-11 | Schmitt Thomas N | Sell | 88 | $47.61 |
| 2025-06-16 | HAUSHILL MARK W | Sell | 11K | $59.07 |
| 2025-06-13 | HAUSHILL MARK W | Sell | 53K | $58.76 |
| 2025-06-06 | Robinson Andrew S | Sell | 36K | $62.65 |
| 2025-06-06 | Robinson Andrew S | Sell | 168 | $63.58 |
| 2025-05-14 | Hill Kirby | Sell | 8.2K | $60.87 |
| 2025-05-09 | Creager Robert E. | Option exercise | 2.8K | — |
| 2025-05-09 | Terry Katharine | Option exercise | 2.8K | — |
| 2025-05-09 | Morrissey Michael J. | Option exercise | 2.8K | — |
| 2025-05-09 | Kuczinski Anthony J | Option exercise | 2.8K | — |
| 2025-05-09 | Hays James Charles | Option exercise | 2.8K | — |
| 2025-05-09 | Ashe Gena L | Option exercise | 2.8K | — |
| 2025-05-09 | Dall Marcia A | Option exercise | 2.8K | — |
| 2025-05-08 | Robinson Andrew S | Sell | 14K | $59.23 |
| 2025-05-08 | HAUSHILL MARK W | Sell | 3.4K | $59.23 |
| 2025-05-07 | Robinson Andrew S | Option exercise | 33K | — |
| 2025-05-07 | HAUSHILL MARK W | Option exercise | 8.3K | — |
| 2025-03-17 | Duffy Sean W | Sell | 5.6K | $48.90 |
| 2025-03-06 | HAUSHILL MARK W | Option exercise | 6.7K | — |
| 2025-03-06 | HAUSHILL MARK W | Sell | 2.4K | $50.24 |
| 2025-03-06 | Robinson Andrew S | Option exercise | 50K | — |
| 2025-03-06 | Robinson Andrew S | Sell | 20K | $50.24 |
| 2025-03-06 | Duffy Sean W | Option exercise | 5.0K | — |
| 2025-03-06 | Duffy Sean W | Sell | 2.0K | $50.24 |
| 2025-03-06 | Duffy Sean W | Option exercise | 5.0K | — |
| 2025-03-06 | Duffy Sean W | Sell | 2.0K | $50.24 |
| 2025-03-06 | Burkhart John A III | Option exercise | 5.9K | — |
| 2025-03-06 | Burkhart John A III | Sell | 2.3K | $50.24 |
| 2025-03-06 | Burkhart John A III | Option exercise | 6.7K | — |
| 2025-03-06 | Bodnar Dan PK | Option exercise | 2.9K | — |
| 2025-03-06 | Bodnar Dan PK | Sell | 1.1K | $50.24 |
| 2025-03-06 | Bodnar Dan PK | Option exercise | 5.0K | — |
| 2025-03-06 | Bodnar Dan PK | Sell | 1.9K | $50.24 |
| 2025-03-06 | Ashe Gena L | Sell | 1.0K | $50.62 |
| 2025-03-06 | Burkhart John A III | Sell | 2.6K | $50.24 |
| 2025-03-06 | Schmitt Thomas N | Option exercise | 4.4K | — |
| 2025-03-06 | Schmitt Thomas N | Sell | 1.7K | $50.24 |
| 2025-03-06 | Schmitt Thomas N | Option exercise | 5.0K | — |
| 2025-03-06 | Schmitt Thomas N | Sell | 1.9K | $50.24 |
| 2025-03-06 | Shaunty Leslie | Option exercise | 2.9K | — |
| 2025-03-06 | Shaunty Leslie | Sell | 828 | $50.24 |
| 2025-03-06 | Shaunty Leslie | Option exercise | 5.0K | — |
| 2025-03-06 | Shaunty Leslie | Sell | 1.4K | $50.24 |
| 2025-03-06 | Hill Kirby | Option exercise | 6.3K | — |
| 2025-03-06 | Hill Kirby | Sell | 2.6K | $50.24 |
| 2025-03-06 | Hill Kirby | Option exercise | 6.7K | — |
| 2025-03-06 | Hill Kirby | Sell | 2.7K | $50.24 |
| 2025-03-06 | Clark Chase M | Option exercise | 1.9K | — |
| 2025-03-06 | Clark Chase M | Sell | 473 | $50.24 |
| 2025-03-06 | Clark Chase M | Option exercise | 2.5K | — |
| 2025-03-06 | Clark Chase M | Sell | 628 | $50.24 |
| 2025-03-06 | Kapadia Sandip A | Option exercise | 2.9K | — |
| 2025-03-06 | Kapadia Sandip A | Sell | 1.1K | $50.24 |
| 2025-03-06 | Kapadia Sandip A | Option exercise | 5.0K | — |
| 2025-03-06 | Kapadia Sandip A | Sell | 1.9K | $50.24 |
| 2025-03-03 | Schmitt Thomas N | Sell | 6.3K | $51.92 |
| 2025-01-08 | Robinson Andrew S | Sell | 262 | $45.53 |
| 2025-01-07 | Robinson Andrew S | Sell | 3.8K | $45.07 |
| 2025-01-07 | Robinson Andrew S | Sell | 4.5K | $45.47 |
| 2025-01-07 | Robinson Andrew S | Sell | 1.3K | $45.51 |
| 2025-01-07 | Robinson Andrew S | Sell | 1.4K | $45.13 |
| 2025-01-06 | Shaunty Leslie | Sell | 344 | $47.07 |
| 2025-01-06 | Kapadia Sandip A | Sell | 444 | $46.99 |
| 2025-01-06 | Kapadia Sandip A | Sell | 464 | $46.97 |
| 2025-01-06 | Schmitt Thomas N | Sell | 546 | $46.85 |
| 2025-01-06 | Robinson Andrew S | Sell | 130 | $47.11 |
| 2025-01-06 | Robinson Andrew S | Sell | 47 | $47.10 |
| 2025-01-03 | Kapadia Sandip A | Sell | 678 | $47.65 |
| 2025-01-03 | Robinson Andrew S | Sell | 9.6K | $47.83 |
| 2025-01-03 | Robinson Andrew S | Sell | 3.7K | $47.62 |
| 2025-01-03 | Kapadia Sandip A | Sell | 551 | $47.82 |
| 2025-01-03 | Shaunty Leslie | Sell | 457 | $47.73 |
| 2025-01-03 | Schmitt Thomas N | Sell | 637 | $47.81 |
| 2025-01-02 | Bodnar Dan PK | Sell | 2.7K | $49.92 |
| 2025-01-02 | Robinson Andrew S | Sell | 6.0K | $49.37 |
| 2025-01-02 | Duffy Sean W | Sell | 1.5K | $49.02 |
| 2025-01-02 | Hill Kirby | Sell | 1.6K | $49.00 |
| 2025-01-02 | HAUSHILL MARK W | Sell | 1.6K | $49.06 |
| 2025-01-02 | Burkhart John A III | Sell | 1.5K | $49.04 |
| 2025-01-02 | Bodnar Dan PK | Sell | 785 | $49.05 |
| 2025-01-02 | Kapadia Sandip A | Sell | 4.3K | $49.51 |
All non-derivative Form 4 activity (SEC), newest first.
Notable events (8-K)
| Date | Items | |
|---|---|---|
| 2026-05-11 | Shareholder vote | filing ↗ |
| 2026-05-06 | ResultsExhibits | filing ↗ |
| 2026-03-17 | Exhibits | filing ↗ |
| 2026-02-26 | Exec/director changeExhibits | filing ↗ |
| 2026-02-23 | ResultsExhibits | filing ↗ |
| 2026-01-06 | Material agreementAcquisition/dispositionDebt obligation3.02Exhibits | filing ↗ |
| 2025-12-03 | Reg FDExhibits | filing ↗ |
| 2025-11-18 | Material agreement1.02Debt obligationExhibits | filing ↗ |
Recent filings
| Form | Filed | Period | Accession |
|---|---|---|---|
| 8-K | 2026-05-11 | 2026-05-11 | 0001519449-26-000041 ↗ |
| 10-Q | 2026-05-11 | 2026-03-31 | 0001519449-26-000039 ↗ |
| 8-K | 2026-05-06 | 2026-05-06 | 0001519449-26-000032 ↗ |
| 8-K/A | 2026-03-17 | 2026-01-06 | 0001519449-26-000018 ↗ |
| 10-K | 2026-03-02 | 2025-12-31 | 0001519449-26-000015 ↗ |
| 8-K | 2026-02-26 | 2026-02-26 | 0001519449-26-000009 ↗ |
| 8-K | 2026-02-23 | 2026-02-23 | 0001519449-26-000005 ↗ |
| 8-K | 2026-01-06 | 2026-01-06 | 0001519449-26-000002 ↗ |
| 8-K | 2025-12-03 | 2025-12-03 | 0001519449-25-000069 ↗ |
| 8-K | 2025-11-18 | 2025-11-18 | 0001519449-25-000066 ↗ |
| 8-K | 2025-11-12 | 2025-11-12 | 0001519449-25-000063 ↗ |
| 10-Q | 2025-11-06 | 2025-09-30 | 0001519449-25-000061 ↗ |