Sean W. Duffy
CIK: 0001936008
Transaction Breakdown
High conviction signal
Position reduction
Derivative conversions
Compensation grants
Gifts, tax withholding, conversions, dispositions to the issuer and other codes
Companies & Roles (1)
Skyward Specialty Insurance Group, Inc.
Discretionary Trading P&L
Holdings
Transaction History (22 total)
- May 6, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Exercise(M)Direct3.8K shares- - May 6, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Tax Payment(F)Direct1.7K shares at avg. $43.68$73K - Feb 26, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Tax Payment(F)Direct1.4K shares at avg. $45.89$64K - Feb 25, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Award(A)Direct2026 LTIP - RSUs
1.4K shares- - Feb 25, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Award(A)Direct2026 Bright Future - RSUs
4.3K shares- - Feb 25, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Exercise(M)Direct3.3K shares- - Feb 25, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Award(A)Direct2026 LTIP - PSUs
1.4K shares- - Jan 12, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Tax Payment(F)Direct2.1K shares at avg. $46.10$97K - Jan 12, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Exercise(M)Direct5K shares- - Jan 12, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Tax Payment(F)Direct2.3K shares at avg. $46.10$105K - Jan 12, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Exercise(M)Direct5K shares- - Jan 1, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Tax Payment(F)Direct1.3K shares at avg. $51.11$65K - Jan 1, 2026SKWD
Skyward Specialty Insurance Group, Inc.
Exercise(M)Direct2.9K shares- - Mar 17, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Sale(S)Direct5.6K shares at avg. $48.90$275K - Mar 6, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Exercise(M)Direct5K shares- - Mar 6, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Sale(S)Direct2K shares at avg. $50.24$101K - Mar 6, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Sale(S)Direct2K shares at avg. $50.24$101K - Mar 6, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Exercise(M)Direct5K shares- - Feb 25, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Award(A)Direct2025 LTIP - PSUs
1.4K shares- - Feb 25, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Award(A)Direct2025 LTIP - RSUs
1.4K shares- - Feb 25, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Award(A)Direct2025 LTIP - PSUs
1.4K shares- - Jan 2, 2025SKWD
Skyward Specialty Insurance Group, Inc.
Sale(S)Direct1.5K shares at avg. $49.02$72K
| Type | Shares | Price | Ownership | |||
|---|---|---|---|---|---|---|
| May 6, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Exercise(M) | 3,805 | - | $0 | Direct |
| May 6, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Tax Payment(F) | 1,671 | $43.68 | $72,989 | Direct |
| Feb 26, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Tax Payment(F) | 1,391 | $45.89 | $63,833 | Direct |
| Feb 25, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Award(A) 2026 LTIP - RSUs | 1,442 | - | - | Direct |
| Feb 25, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Award(A) 2026 Bright Future - RSUs | 4,326 | - | - | Direct |
| Feb 25, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Exercise(M) | 3,318 | - | $0 | Direct |
| Feb 25, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Award(A) 2026 LTIP - PSUs | 1,442 | - | - | Direct |
| Jan 12, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Tax Payment(F) | 2,095 | $46.10 | $96,580 | Direct |
| Jan 12, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Exercise(M) | 5,000 | - | $0 | Direct |
| Jan 12, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Tax Payment(F) | 2,276 | $46.10 | $104,924 | Direct |
| Jan 12, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Exercise(M) | 5,000 | - | $0 | Direct |
| Jan 1, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Tax Payment(F) | 1,267 | $51.11 | $64,756 | Direct |
| Jan 1, 2026 | SKWD Skyward Specialty Insurance Group, Inc. | Exercise(M) | 2,861 | - | $0 | Direct |
| Mar 17, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Sale(S) | 5,625 | $48.90 | $275,063 | Direct |
| Mar 6, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Exercise(M) | 5,000 | - | - | Direct |
| Mar 6, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Sale(S) | 2,008 | $50.24 | $100,882 | Direct |
| Mar 6, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Sale(S) | 2,002 | $50.24 | $100,580 | Direct |
| Mar 6, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Exercise(M) | 4,993 | - | - | Direct |
| Feb 25, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Award(A) 2025 LTIP - PSUs | 1,351 | - | - | Direct |
| Feb 25, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Award(A) 2025 LTIP - RSUs | 1,351 | - | - | Direct |
| Feb 25, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Award(A) 2025 LTIP - PSUs | 1,351 | - | - | Direct |
| Jan 2, 2025 | SKWD Skyward Specialty Insurance Group, Inc. | Sale(S) | 1,475 | $49.02 | $72,305 | Direct |
1-22 of 22 transactions
About Duffy Sean W
Duffy Sean W (SEC CIK 0001936008) files insider reports with the SEC as EVP & Chief Claims Officer of Skyward Specialty Insurance Group, Inc. (SKWD).
Signal8 holds 8 ownership filings by Duffy Sean W, all Form 4s, filed between Jan 6, 2025 and May 8, 2026. Those filings report 22 transactions, from Jan 2, 2025 to May 6, 2026. Signal8's Form 4 history starts in Sep 2024.
The business address on Duffy Sean W's filings is in HOUSTON, TX.
Recent filings by Duffy Sean W
- May 6, 2026: Option exercise of SKWD shares (Form 4, code M).
- May 6, 2026: Tax withholding of SKWD shares (Form 4, code F).
- Feb 26, 2026: Tax withholding of SKWD shares (Form 4, code F).
- Feb 25, 2026: Grants or awards of SKWD derivative securities (2 lines, Form 4, code A).
- Feb 25, 2026: Option exercise of SKWD shares (Form 4, code M).
Other insiders filing for Skyward Specialty Insurance Group, Inc. (SKWD)
- HEARN PETER C, Director
- Schmitt Thomas N, CPO, Skyward Group
- Kuczinski Anthony J, Director
- Ashe Gena L, Director
- Kapadia Sandip A, Head of Actuarial
- Bodnar Dan PK, Chief Information Officer