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Company Analysis

SKWD Insider Trading

Skyward Specialty Insurance Group, Inc. | Fire, Marine & Casualty Insurance

Comprehensive Trading Performance Summary

The investment history of corporate insiders at Skyward Specialty Insurance Group, Inc. provides a unique lens into the internal conviction of the company's leadership. By analyzing SEC Form 4 filings, investors can track how directors and officers are allocating their own capital. High-conviction buying often signals that management believes the current market price significantly undervalues future growth prospects, while strategic selling might occur for personal liquidity or portfolio diversification. Monitoring these shifts in ownership is essential for understanding the alignment between management and shareholders in the Fire, Marine & Casualty Insurance sector.

Transactions on Chart

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Filing Date Trade Date Reporting Person Relationship Type Price Qty Total, $ Owned After Change, %
2026-05-21 21:27 2026-05-21 Kuczinski Anthony J Director BUY $47.10 2,000 $94,200 15,977 +14.3%
2026-05-12 20:49 2026-05-11 Ashe Gena L Director OPT+S $46.35 740 $34,299 4,570 0.0%
2026-03-04 21:59 2026-02-27 Kuczinski Anthony J Director BUY $47.89 5,000 $239,465 11,903 +72.4%
2026-03-03 21:09 2026-02-27 McHarg Taryn Leonie Officer, Other - CFO - Apollo BUY $46.60 200 $9,320 100 +100.0%
2026-03-03 18:19 2026-03-02 Peirce Christopher Locke Director BUY $47.30 3,200 $151,360 3,200 +100.0%
2026-02-28 00:56 2026-02-27 Robinson Andrew S Director, Officer - Chairman & CEO, Skyward Group BUY $46.76 22,100 $1,033,369 167,674 +15.2%
2026-02-11 00:05 2026-02-09 Schmitt Thomas N Officer - CPO, Skyward Group SELL $43.49 2,616 $113,774 14,747 -15.1%
2025-12-20 00:05 2025-12-18 Kapadia Sandip A Officer - Head of Actuarial SELL $50.01 5,030 $251,550 8,059 -38.4%
2025-12-17 00:05 2025-12-12 Kapadia Sandip A Officer - Head of Actuarial SELL $50.02 2,686 $134,357 13,089 -17.0%
2025-12-12 01:29 2025-12-11 Schmitt Thomas N Officer - CHIEF PEOPLE & ADMIN.OFFICER SELL $47.61 88 $4,190 9,959 -0.9%
2025-06-17 23:05 2025-06-13 HAUSHILL MARK W Officer - EVP & CFO SELL $58.81 63,314 $3,723,693 123,063 -34.0%
2025-06-10 22:05 2025-06-06 Robinson Andrew S Director, Officer - CHAIRMAN & CEO SELL $62.65 36,271 $2,272,375 65,269 -35.7%
2025-05-15 23:33 2025-05-14 Hill Kirby Officer - Chairman, Captives & Programs SELL $60.87 8,249 $502,135 8,249 -50.0%
2025-05-09 23:05 2025-05-08 Robinson Andrew S Director, Officer - CHAIRMAN & CEO OPT+S $59.23 13,786 $816,570 101,540 0.0%
2025-05-09 23:05 2025-05-08 HAUSHILL MARK W Officer - EVP & CFO OPT+S $59.23 3,447 $204,172 186,146 0.0%
2025-03-18 23:47 2025-03-17 Duffy Sean W Officer - EVP & CHIEF CLAIMS OFFICER SELL $48.90 5,625 $275,063 8,813 -39.0%
2025-03-10 23:37 2025-03-06 Schmitt Thomas N Officer - CHIEF PEOPLE & ADMIN. OFFICER OPT+S $50.24 3,625 $182,120 9,727 0.0%
2025-03-10 23:35 2025-03-06 Shaunty Leslie Officer - GENERAL COUNSEL & SECRETARY OPT+S $50.24 2,240 $112,537 26,104 0.0%
2025-03-10 23:34 2025-03-06 Hill Kirby Officer - PRESIDENT - INDUSTRY SOLUTIONS OPT+S $50.24 5,269 $264,714 16,498 0.0%
2025-03-10 23:33 2025-03-06 Clark Chase M Officer - Chief Underwriting Officer OPT+S $50.24 1,101 $55,314 3,279 0.0%
2025-03-10 23:31 2025-03-06 Kapadia Sandip A Officer - EVP, CHIEF ACTUARY OPT+S $50.24 2,961 $148,760 15,347 0.0%
2025-03-10 23:27 2025-03-06 Duffy Sean W Officer - EVP & CHIEF CLAIMS OFFICER OPT+S $50.24 4,010 $201,462 14,438 0.0%
2025-03-10 23:26 2025-03-06 Burkhart John A III Officer - PRESIDENT - SPECIALTY LINES OPT+S $50.24 4,832 $242,759 21,750 0.0%
2025-03-10 23:25 2025-03-06 Bodnar Dan PK Officer - CHIEF INFORMATION OFFICER OPT+S $50.24 3,059 $153,684 17,340 0.0%
2025-03-10 23:23 2025-03-06 Ashe Gena L Director SELL $50.62 1,000 $50,615 734 -57.7%
2025-03-10 23:28 2025-03-06 Robinson Andrew S Director, Officer - CHAIRMAN & CEO OPT+S $50.24 20,311 $1,020,423 82,044 0.0%
2025-03-10 23:30 2025-03-06 HAUSHILL MARK W Officer - EVP & CFO OPT+S $50.24 2,363 $118,717 181,273 0.0%
2025-03-05 01:12 2025-03-03 Schmitt Thomas N Officer - CHIEF PEOPLE & ADMIN. OFFICER SELL $51.92 6,300 $327,096 3,946 -61.5%
2025-01-11 00:10 2025-01-07 Robinson Andrew S Director, Officer - CHAIRMAN & CEO SELL $45.30 11,274 $510,694 52,355 -17.7%
2025-01-07 03:39 2025-01-02 Kapadia Sandip A Officer - EVP, CHIEF ACTUARY SELL $48.82 6,484 $316,548 10,371 -38.5%
2025-01-07 03:28 2025-01-03 Shaunty Leslie Officer - GENERAL COUNSEL & SECRETARY SELL $47.45 801 $38,006 20,407 -3.8%
2025-01-07 03:25 2025-01-03 Schmitt Thomas N Officer - CHIEF PEOPLE & ADMIN. OFFICER SELL $47.37 1,183 $56,035 10,246 -10.4%
2025-01-07 03:20 2025-01-02 Hill Kirby Officer - PRESIDENT - INDUSTRY SOLUTIONS SELL $49.00 1,560 $76,446 8,786 -15.1%
2025-01-07 03:16 2025-01-02 Burkhart John A III Officer - PRESIDENT - SPECIALTY LINES SELL $49.04 1,465 $71,844 14,042 -9.4%
2025-01-07 03:15 2025-01-02 Bodnar Dan PK Officer - CHIEF INFORMATION OFFICER SELL $49.72 3,484 $173,238 12,462 -21.8%
2025-01-07 03:14 2025-01-02 Duffy Sean W Officer - EVP & CHIEF CLAIMS OFFICER SELL $49.02 1,475 $72,305 8,455 -14.9%
2025-01-07 03:43 2025-01-02 Robinson Andrew S Director, Officer - CHAIRMAN & CEO SELL $48.26 19,525 $942,232 63,629 -23.5%
2025-01-07 03:18 2025-01-02 HAUSHILL MARK W Officer - EVP & CFO SELL $49.06 1,630 $79,965 176,971 -0.9%
2024-12-10 00:52 2024-12-05 Hays James Charles Director SELL $54.84 27,950 $1,532,686 669,311 -4.0%
2024-12-05 02:48 2024-12-03 Hays James Charles Director SELL $54.15 75,000 $4,061,018 697,261 -9.7%
2024-12-03 00:27 2024-11-27 Hays James Charles Director SELL $53.87 33,539 $1,806,910 772,261 -4.2%
2024-11-06 00:04 2024-11-04 Hill Kirby Officer - PRESIDENT - INDUSTRY SOLUTIONS SELL $43.07 3,600 $155,052 10,346 -25.8%
2024-08-09 23:11 2024-08-09 Terry Katharine Director SELL $36.87 1,653 $60,946 4,001 -29.2%
2024-05-13 23:42 2024-05-10 Hill Kirby Officer - PRESIDENT - INDUSTRY SOLUTIONS SELL $37.02 8,500 $314,670 13,946 -37.9%
2024-05-13 23:38 2024-05-10 Robinson Andrew S Director, Officer - CHAIRMAN & CEO OPT+S $37.21 23,533 $875,663 83,154 0.0%
2024-05-13 23:40 2024-05-10 HAUSHILL MARK W Officer - EVP & CFO OPT+S $37.18 3,244 $120,612 177,886 0.0%
2024-05-14 03:28 2024-05-09 WESTAIM Corp 10% owner SELL $36.50 5,060,000 $184,690,000 1,919,639 -72.5%
2024-03-13 23:08 2024-03-11 Robinson Andrew S Director, Officer - CHAIRMAN & CEO SELL $35.78 27,650 $989,441 46,883 -37.1%
2024-03-09 01:13 2024-03-06 Robinson Andrew S Director, Officer - CHAIRMAN & CEO SELL $35.58 35,724 $1,270,988 74,533 -32.4%
2024-03-06 00:23 2024-03-01 Kuczinski Anthony J Director BUY $36.17 400 $14,468 4,124 +10.7%
SHOW ENTRIES

How to Interpret $SKWD Trades

Not every insider transaction in Skyward Specialty Insurance Group, Inc. is a signal for immediate action. Professional investors look for "cluster buying"—when multiple executives simultaneously purchase $SKWD shares on the open market. It is crucial to distinguish between scheduled sales (under Rule 10b5-1) and voluntary increases in ownership, which demonstrate management’s true conviction that the stock is undervalued.

Data Source & Accuracy for SKWD

Insider activity data for Skyward Specialty Insurance Group, Inc. is streamed in real-time directly from the SEC EDGAR system. We analyze raw Form 4 filings, filtering out technical adjustments and complex derivative transactions. This provides a transparent view of how ownership structure is evolving in $SKWD, allowing you to follow the capital of those with the most intimate knowledge of the company.

UNDERSTANDING THE DATA

FILING DATE: The date and time when the transaction was reported to the SEC. This is when the public first receives the information.

TRADE DATE: The actual day the insider executed the purchase or sale in the market.

INDUSTRY: The specific market sector the company operates in. Useful for identifying broader institutional capital flows across sectors.

OWNED AFTER: The total number of shares held by the insider following the transaction. This highlights the insider's remaining conviction in the company.

CHANGE %: The percentage increase or decrease of the insider's total position. Large percentage changes often carry more weight than the dollar amount alone.

TRADE TYPES DEFINITIONS

BUY: An open market purchase. Typically indicates an insider's belief that the stock is undervalued or poised for growth.

SELL: An open market sale. While often used for diversification or liquidity, large or unexpected sales can be a warning signal.

OPT+S (OPTION EXERCISE & SALE): This occurs when an insider exercises their stock options and sells them immediately. Often part of a structured compensation plan.