Skyward Specialty Insurance Group, Inc. (SKWD)

Latest Insider Confidence Score

2026Q1

42.1
Bearish

Company insider confidence (by quarter)

2023Q1 2026Q1

Largest shareholders

Insider Role (last 12 mo) Shares held Filed at
Hays James Charles Director 2,809,269 May 13, 2024
WESTAIM Corp 10% Owner 1,919,639 May 13, 2024
Haushill Mark W CFO 123,063 Jun 17, 2025
Robinson Andrew S CEO 65,269 Jun 10, 2025
Duffy Sean W EVP & CHIEF CLAIMS OFFICER 8,813 Mar 18, 2025

Recent buy/sell transactions

Exec date Filing date Insider Role Signal Confidence Shares % of shares Under plan? Amount (USD)
Feb 27, 2026 Mar 4, 2026 Kuczinski Anthony J Director Buy 95.0 +5,000 72.43% ✗ $239.5K
Feb 27, 2026 Mar 3, 2026 McHarg Taryn Leonie CFO Buy 82.5 +200 2.58% ✗ $9.3K
Mar 2, 2026 Mar 3, 2026 Peirce Christopher Locke Director Buy 95.0 +3,200 100.00% ✗ $151.4K
Feb 27, 2026 Feb 27, 2026 Robinson Andrew S CEO Buy 100.0 +22,100 15.18% ✗ $1M
Feb 25, 2026 Feb 27, 2026 McHarg Taryn Leonie CFO Neutral 52.5 - 0.00% ✗ -
Feb 25, 2026 Feb 27, 2026 Slaughter James Richard CUO - Apollo Neutral 52.5 - 0.00% ✗ -
Feb 25, 2026 Feb 27, 2026 Ibeson David Christopher Ben CEO Neutral 52.5 - 0.00% ✗ -
Feb 25, 2026 Feb 27, 2026 Khan Shakoor Corp. Dev. Officer Neutral 52.5 - 0.00% ✗ -
Feb 25, 2026 Feb 27, 2026 RYAN PATRICIA A. Chief Legal Officer Neutral 52.5 - 0.00% ✗ -
Feb 25, 2026 Feb 27, 2026 Kapadia Sandip A Head of Actuarial Sell 46.3 -847 -4.74% ✗ $38.9K
Feb 25, 2026 Feb 27, 2026 Bodnar Dan PK Chief Information Officer Sell 46.3 -876 -3.20% ✗ $40.2K
Feb 25, 2026 Feb 27, 2026 Schmitt Thomas N CPO, Skyward Group Sell 42.5 -1,153 -6.52% ✗ $52.9K
Feb 25, 2026 Feb 27, 2026 HAUSHILL MARK W CFO Sell 42.5 -1,436 -1.04% ✗ $65.9K
Feb 25, 2026 Feb 27, 2026 Duffy Sean W EVP & Chief Claims Officer Sell 42.5 -1,391 -7.19% ✗ $63.8K
Feb 25, 2026 Feb 27, 2026 Burkhart John A III President Sell 42.5 -1,652 -4.53% ✗ $75.8K
Feb 25, 2026 Feb 27, 2026 Robinson Andrew S CEO Sell 40.0 -6,916 -4.54% ✗ $317.4K
Feb 9, 2026 Feb 10, 2026 Schmitt Thomas N CPO, Skyward Group Sell 21.3 -2,616 -15.07% ✓ $113.8K
Feb 2, 2026 Peirce Christopher Locke Director Neutral 52.5 - 0.00% ✗ -
Jan 12, 2026 Jan 14, 2026 Schmitt Thomas N CPO, Skyward Group Sell 42.5 -4,117 -11.50% ✗ $189.8K
Jan 12, 2026 Jan 14, 2026 Duffy Sean W EVP & Chief Claims Officer Sell 42.5 -4,371 -13.03% ✗ $201.5K
Jan 12, 2026 Jan 14, 2026 Kapadia Sandip A Head of Actuarial Sell 42.5 -3,793 -11.97% ✗ $174.9K
Jan 12, 2026 Jan 14, 2026 Burkhart John A III President Sell 42.5 -5,421 -8.22% ✗ $249.9K
Jan 12, 2026 Jan 14, 2026 Robinson Andrew S CEO Sell 37.5 -39,532 -14.17% ✗ $1.8M
Jan 14, 2026 Robinson Andrew S CEO Neutral 57.5 - 0.00% ✓ -
Jan 12, 2026 Jan 14, 2026 Bodnar Dan PK Chief Information Officer Sell 42.5 -3,917 -7.71% ✗ $180.6K
Jan 12, 2026 Jan 14, 2026 HAUSHILL MARK W CFO Sell 42.5 -5,420 -2.02% ✗ $249.9K
Jan 1, 2026 Jan 5, 2026 Schmitt Thomas N CPO, Skyward Group Sell 42.5 -1,004 -8.04% ✗ $51.3K
Jan 1, 2026 Jan 5, 2026 Duffy Sean W EVP & CHIEF CLAIMS OFFICER Sell 42.5 -1,267 -10.85% ✗ $64.8K
Jan 1, 2026 Jan 5, 2026 Bodnar Dan PK CHIEF INFORMATION OFFICER Sell 46.3 -765 -3.89% ✗ $39.1K
Jan 1, 2026 Jan 5, 2026 Kapadia Sandip A Head of Actuarial Sell 46.3 -741 -7.35% ✗ $37.9K
Jan 1, 2026 Jan 5, 2026 HAUSHILL MARK W CFO Sell 42.5 -1,501 -1.18% ✗ $76.7K
Jan 1, 2026 Jan 5, 2026 Robinson Andrew S CEO Sell 40.0 -5,973 -7.43% ✗ $305.3K
Jan 1, 2026 Jan 5, 2026 Burkhart John A III President Sell 42.5 -1,435 -5.56% ✗ $73.3K
Jan 1, 2026 Jan 5, 2026 McHarg Taryn Leonie CFO Neutral 90.0 +7,764 100.00% ✗ -
Jan 1, 2026 Jan 5, 2026 Hays James Charles Director Neutral 85.0 +143,664 5.37% ✗ -
Jan 1, 2026 Jan 5, 2026 Slaughter James Richard CUO - Apollo Neutral 90.0 +68,199 100.00% ✗ -
Jan 1, 2026 Jan 5, 2026 Ibeson David Christopher Ben CEO Neutral 90.0 +346,575 100.00% ✗ -
Jan 5, 2026 McHarg Taryn Leonie CFO Neutral 52.5 - 0.00% ✗ -
Jan 5, 2026 Slaughter James Richard CUO - Apollo Neutral 52.5 - 0.00% ✗ -
Jan 5, 2026 Ibeson David Christopher Ben CEO Neutral 52.5 - 0.00% ✗ -
Dec 18, 2025 Dec 19, 2025 Kapadia Sandip A Head of Actuarial Sell 7.5 -5,030 -38.43% ✓ $251.6K
Dec 12, 2025 Dec 16, 2025 Kapadia Sandip A Head of Actuarial Sell 20.0 -2,686 -17.03% ✓ $134.4K
Dec 11, 2025 Dec 11, 2025 Schmitt Thomas N CHIEF PEOPLE & ADMIN.OFFICER Sell 52.5 -88 -0.88% ✓ $4.2K
Jun 13, 2025 Jun 17, 2025 HAUSHILL MARK W CFO Sell 5.0 -63,314 -33.97% ✓ $3.7M
Jun 6, 2025 Jun 10, 2025 Robinson Andrew S CEO Sell 5.0 -36,271 -35.72% ✓ $2.3M
May 14, 2025 May 15, 2025 Hill Kirby Chair Sell 20.0 -8,249 -50.00% ✗ $502.1K
May 9, 2025 May 9, 2025 Hays James Charles Director Neutral 52.5 - 0.00% ✗ -
May 9, 2025 May 9, 2025 Dall Marcia A Director Neutral 52.5 - 0.00% ✗ -
May 7, 2025 May 9, 2025 HAUSHILL MARK W CFO Sell 22.5 -3,447 -1.82% ✗ $204.2K
May 9, 2025 May 9, 2025 Creager Robert E. Director Neutral 52.5 - 0.00% ✗ -
May 9, 2025 May 9, 2025 Terry Katharine Director Neutral 52.5 - 0.00% ✗ -
May 9, 2025 May 9, 2025 Morrissey Michael J. Director Neutral 52.5 - 0.00% ✗ -
May 7, 2025 May 9, 2025 RYAN PATRICIA A. GENERAL COUNSEL & SECRETARY Neutral 52.5 - 0.00% ✗ -
May 9, 2025 May 9, 2025 Kuczinski Anthony J Director Neutral 52.5 - 0.00% ✗ -
May 7, 2025 May 9, 2025 Robinson Andrew S CEO Sell 20.0 -13,786 -11.95% ✗ $816.6K
May 9, 2025 May 9, 2025 Ashe Gena L Director Neutral 52.5 - 0.00% ✗ -
Apr 1, 2025 RYAN PATRICIA A. GENERAL COUNSEL & SECRETARY Neutral 52.5 - 0.00% ✗ -
Mar 17, 2025 Mar 18, 2025 Duffy Sean W EVP & CHIEF CLAIMS OFFICER Sell 7.5 -5,625 -38.96% ✓ $275.1K
Mar 6, 2025 Mar 10, 2025 Schmitt Thomas N CHIEF PEOPLE & ADMIN. OFFICER Sell 22.5 -3,625 -18.12% ✗ $182.1K
Mar 6, 2025 Mar 10, 2025 Shaunty Leslie GENERAL COUNSEL & SECRETARY Sell 22.5 -2,240 -4.40% ✗ $112.5K
Mar 6, 2025 Mar 10, 2025 Hill Kirby President Sell 20.0 -5,269 -15.36% ✗ $264.7K
Mar 6, 2025 Mar 10, 2025 Clark Chase M Chief Underwriting Officer Sell 22.5 -1,101 -19.03% ✗ $55.3K
Mar 6, 2025 Mar 10, 2025 Kapadia Sandip A EVP, CHIEF ACTUARY Sell 22.5 -2,961 -9.70% ✗ $148.8K
Mar 6, 2025 Mar 10, 2025 HAUSHILL MARK W CFO Sell 22.5 -2,363 -1.29% ✗ $118.7K
Mar 6, 2025 Mar 10, 2025 Robinson Andrew S CEO Sell 17.5 -20,311 -19.84% ✗ $1M
Mar 6, 2025 Mar 10, 2025 Duffy Sean W EVP & CHIEF CLAIMS OFFICER Sell 22.5 -4,010 -13.41% ✗ $201.5K
Mar 6, 2025 Mar 10, 2025 Burkhart John A III President Sell 22.5 -4,832 -10.92% ✗ $242.8K
Mar 6, 2025 Mar 10, 2025 Bodnar Dan PK CHIEF INFORMATION OFFICER Sell 22.5 -3,059 -8.82% ✗ $153.7K
Mar 6, 2025 Mar 10, 2025 Ashe Gena L Director Sell 22.5 -1,000 -57.67% ✗ $50.6K
Mar 3, 2025 Mar 4, 2025 Schmitt Thomas N CHIEF PEOPLE & ADMIN. OFFICER Sell 7.5 -6,300 -61.49% ✓ $327.1K
Feb 25, 2025 Feb 27, 2025 Khan Shakoor SVP CORP. DEVELOPMENT Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 Clark Chase M Chief Underwriting Officer Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 Bodnar Dan PK CHIEF INFORMATION OFFICER Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 Schmitt Thomas N CHIEF PEOPLE & ADMIN. OFFICER Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 Duffy Sean W EVP & CHIEF CLAIMS OFFICER Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 Kapadia Sandip A EVP, CHIEF ACTUARY Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 Burkhart John A III President Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 HAUSHILL MARK W CFO Neutral 52.5 - 0.00% ✗ -
Feb 25, 2025 Feb 27, 2025 Robinson Andrew S CEO Neutral 52.5 - 0.00% ✗ -
Jan 15, 2025 Kuczinski Anthony J Director Neutral 52.5 - 0.00% ✗ -
Jan 7, 2025 Jan 10, 2025 Robinson Andrew S CEO Sell 17.5 -11,274 -17.72% ✓ $510.7K
Jan 2, 2025 Jan 6, 2025 Robinson Andrew S CEO Sell 12.5 -19,525 -23.48% ✓ $942.2K
Jan 2, 2025 Jan 6, 2025 Kapadia Sandip A EVP, CHIEF ACTUARY Sell 7.5 -6,484 -38.47% ✓ $316.5K
Jan 3, 2025 Jan 6, 2025 Shaunty Leslie GENERAL COUNSEL & SECRETARY Sell 41.3 -801 -3.78% ✓ $38K
Jan 3, 2025 Jan 6, 2025 Schmitt Thomas N CHIEF PEOPLE & ADMIN. OFFICER Sell 25.0 -1,183 -10.35% ✓ $56K
Jan 2, 2025 Jan 6, 2025 Hill Kirby President Sell 20.0 -1,560 -15.08% ✓ $76.4K
Jan 2, 2025 Jan 6, 2025 HAUSHILL MARK W CFO Sell 47.5 -1,630 -0.91% ✓ $80K
Jan 2, 2025 Jan 6, 2025 Burkhart John A III President Sell 28.8 -1,465 -9.45% ✓ $71.8K
Jan 2, 2025 Jan 6, 2025 Bodnar Dan PK CHIEF INFORMATION OFFICER Sell 15.0 -3,484 -21.85% ✓ $173.2K
Jan 2, 2025 Jan 6, 2025 Duffy Sean W EVP & CHIEF CLAIMS OFFICER Sell 25.0 -1,475 -14.85% ✓ $72.3K
Dec 5, 2024 Dec 9, 2024 Hays James Charles Director Sell 17.5 -27,950 -1.03% ✗ $1.5M
Dec 3, 2024 Dec 4, 2024 Hays James Charles Director Sell 17.5 -75,000 -2.70% ✗ $4.1M
Nov 27, 2024 Dec 2, 2024 Hays James Charles Director Sell 17.5 -33,539 -1.19% ✗ $1.8M
Nov 4, 2024 Nov 5, 2024 Hill Kirby President Sell 22.5 -3,600 -25.81% ✗ $155.1K
Aug 8, 2024 Aug 9, 2024 Clark Chase M President Neutral 52.5 - 0.00% ✗ -
Aug 9, 2024 Clark Chase M President Neutral 52.5 - 0.00% ✗ -
Aug 9, 2024 Khan Shakoor SVP CORP. DEVELOPMENT Neutral 52.5 - 0.00% ✗ -
Aug 9, 2024 Aug 9, 2024 Terry Katharine Director Sell 22.5 -1,653 -29.24% ✗ $60.9K
May 9, 2024 May 13, 2024 WESTAIM Corp 10% Owner Sell 15.0 -5,060,000 -72.50% ✗ $184.7M
May 9, 2024 May 13, 2024 Terry Katharine Director Neutral 52.5 - 0.00% ✗ -