Skyward Specialty Insurance Group, Inc. (SKWD) Insider Trading

Last 12 months

Insiders bought $1.53M and sold $969k on the open market.

52% of the selling was scheduled in advance under 10b5-1 plans. CPO, Skyward Group Thomas N Schmitt sold $431k on Jun 12, 45% of their stake, outside a plan.

Net open-market

+$559k

5 buys · 6 sales

Under a 10b5-1 plan

52%

of the value sold

Insiders who bought / sold

4 / 3

executives and directors

Last open-market buy

May 2026

May 21, 2026

Get an email when SKWD's executives or directors buy, or make a large sale outside a plan.

Trades · last 2 years

Date	Insider	Trade	Shares	Price	Value	Of their stake	Filing
Jun 12	Thomas N Schmitt CPO, Skyward Group	SoldNo plan	8,397	$51.32	$431k	45%	Form 4
May 21	Anthony J Kuczinski Director	Bought 3 parts	2,000	$47.10 average	$94k	14%	Form 4
May 11	Gena L Ashe Director	SoldNo plan 3 parts	740	$46.35 average	$34k	14%	Form 4
Feb 27 – Mar 3	Anthony J Kuczinski Director	Bought 3 parts	5,000	$47.89 average	$239k	72%	Form 4
Mar 2	Christopher Locke Peirce Director	Bought	3,200	$47.30	$151k	New	Form 4
Feb 27	Taryn Leonie McHarg CFO - Apollo	Bought 2 parts	200	$46.60 average	$9k	2.6%	Form 4
Feb 27	Andrew S Robinson Chairman & CEO, Skyward Group	Bought 2 parts	22,100	$46.76 average	$1.03M	15%	Form 4
Feb 9	Thomas N Schmitt CPO, Skyward Group	Sold10b5-1 plan	2,616	$43.49	$114k	15%	Form 4
Dec 18, 2025	Sandip A Kapadia Head of Actuarial	Sold10b5-1 plan	5,030	$50.01	$252k	38%	Form 4
Dec 12, 2025	Sandip A Kapadia Head of Actuarial	Sold10b5-1 plan 2 parts	2,686	$50.02 average	$134k	17%	Form 4
Dec 11, 2025	Thomas N Schmitt CHIEF PEOPLE & ADMIN.OFFICER	Sold10b5-1 plan	88	$47.61	$4k	0.9%	Form 4
Jun 13, 2025 – Jun 16, 2025	Mark W Haushill EVP & CFO	Sold10b5-1 plan 2 parts	63,314	$58.81 average	$3.72M	34%	Form 4
Jun 6, 2025	Andrew S Robinson CHAIRMAN & CEO	Sold10b5-1 plan 2 parts	36,271	$62.65 average	$2.27M	36%	Form 4
May 14, 2025	Kirby Hill Chairman, Captives & Programs	SoldNo plan	8,249	$60.87	$502k	50%	Form 4
May 8, 2025	Mark W Haushill EVP & CFO	SoldNo plan	3,447	$59.23	$204k	1.8%	Form 4
May 8, 2025	Andrew S Robinson CHAIRMAN & CEO	SoldNo plan	13,786	$59.23	$817k	12%	Form 4
Mar 17, 2025	Sean W Duffy EVP & CHIEF CLAIMS OFFICER	Sold10b5-1 plan	5,625	$48.90	$275k	39%	Form 4
Mar 6, 2025	Thomas N Schmitt CHIEF PEOPLE & ADMIN. OFFICER	SoldNo plan 2 parts	3,625	$50.24 average	$182k	27%	Form 4
Mar 6, 2025	Leslie Shaunty GENERAL COUNSEL & SECRETARY	SoldNo plan 2 parts	2,240	$50.24 average	$113k	7.9%	Form 4
Mar 6, 2025	Kirby Hill PRESIDENT - INDUSTRY SOLUTIONS	SoldNo plan 2 parts	5,269	$50.24 average	$265k	24%	Form 4
Mar 6, 2025	Chase M Clark Chief Underwriting Officer	SoldNo plan 2 parts	1,101	$50.24 average	$55k	25%	Form 4
Mar 6, 2025	Sandip A Kapadia EVP, CHIEF ACTUARY	SoldNo plan 2 parts	2,961	$50.24 average	$149k	16%	Form 4
Mar 6, 2025	Mark W Haushill EVP & CFO	SoldNo plan	2,363	$50.24	$119k	1.3%	Form 4
Mar 6, 2025	Andrew S Robinson CHAIRMAN & CEO	SoldNo plan	20,311	$50.24	$1.02M	20%	Form 4
Mar 6, 2025	Sean W Duffy EVP & CHIEF CLAIMS OFFICER	SoldNo plan 2 parts	4,010	$50.24 average	$201k	22%	Form 4
Mar 6, 2025	John A Burkhart III PRESIDENT - SPECIALTY LINES	SoldNo plan 2 parts	4,832	$50.24 average	$243k	18%	Form 4
Mar 6, 2025	Dan Pk Bodnar CHIEF INFORMATION OFFICER	SoldNo plan 2 parts	3,059	$50.24 average	$154k	15%	Form 4
Mar 6, 2025	Gena L Ashe Director	SoldNo plan	1,000	$50.62	$51k	58%	Form 4
Mar 3, 2025	Thomas N Schmitt CHIEF PEOPLE & ADMIN. OFFICER	Sold10b5-1 plan	6,300	$51.92	$327k	61%	Form 4
Jan 7, 2025 – Jan 8, 2025	Andrew S Robinson CHAIRMAN & CEO	Sold10b5-1 plan 5 parts	11,274	$45.30 average	$511k	18%	Form 4
Jan 2, 2025 – Jan 6, 2025	Andrew S Robinson CHAIRMAN & CEO	Sold10b5-1 plan 5 parts	19,525	$48.26 average	$942k	23%	Form 4
Jan 2, 2025 – Jan 6, 2025	Sandip A Kapadia EVP, CHIEF ACTUARY	Sold10b5-1 plan 5 parts	6,484	$48.82 average	$317k	38%	Form 4
Jan 3, 2025 – Jan 6, 2025	Leslie Shaunty GENERAL COUNSEL & SECRETARY	Sold10b5-1 plan 2 parts	801	$47.45 average	$38k	3.8%	Form 4
Jan 3, 2025 – Jan 6, 2025	Thomas N Schmitt CHIEF PEOPLE & ADMIN. OFFICER	Sold10b5-1 plan 2 parts	1,183	$47.37 average	$56k	10%	Form 4
Jan 2, 2025	Kirby Hill PRESIDENT - INDUSTRY SOLUTIONS	Sold10b5-1 plan	1,560	$49.00	$76k	15%	Form 4
Jan 2, 2025	Mark W Haushill EVP & CFO	Sold10b5-1 plan	1,630	$49.06	$80k	0.9%	Form 4
Jan 2, 2025	John A Burkhart III PRESIDENT - SPECIALTY LINES	Sold10b5-1 plan	1,465	$49.04	$72k	9.4%	Form 4
Jan 2, 2025	Dan Pk Bodnar CHIEF INFORMATION OFFICER	Sold10b5-1 plan 2 parts	3,484	$49.72 average	$173k	22%	Form 4
Jan 2, 2025	Sean W Duffy EVP & CHIEF CLAIMS OFFICER	Sold10b5-1 plan	1,475	$49.02	$72k	15%	Form 4
Dec 5, 2024	James Charles Hays Director	SoldNo plan	27,950	$54.84	$1.53M	1.0%	Form 4

Jun 12No plan
Thomas N Schmitt
CPO, Skyward Group · sold 8,397 at $51.32
$431k
45% of stake
May 21
Anthony J Kuczinski
Director · bought 2,000 at avg $47.10
$94k
14% of stake
May 11No plan
Gena L Ashe
Director · sold 740 at avg $46.35
$34k
14% of stake
Feb 27 – Mar 3
Anthony J Kuczinski
Director · bought 5,000 at avg $47.89
$239k
72% of stake
Mar 2
Christopher Locke Peirce
Director · bought 3,200 at $47.30
$151k
New position
Feb 27
Taryn Leonie McHarg
CFO - Apollo · bought 200 at avg $46.60
$9k
2.6% of stake
Feb 27
Andrew S Robinson
Chairman & CEO, Skyward Group · bought 22,100 at avg $46.76
$1.03M
15% of stake
Feb 910b5-1 plan
Thomas N Schmitt
CPO, Skyward Group · sold 2,616 at $43.49
$114k
15% of stake
Dec 18, 202510b5-1 plan
Sandip A Kapadia
Head of Actuarial · sold 5,030 at $50.01
$252k
38% of stake
Dec 12, 202510b5-1 plan
Sandip A Kapadia
Head of Actuarial · sold 2,686 at avg $50.02
$134k
17% of stake
Dec 11, 202510b5-1 plan
Thomas N Schmitt
CHIEF PEOPLE & ADMIN.OFFICER · sold 88 at $47.61
$4k
0.9% of stake
Jun 13, 2025 – Jun 16, 202510b5-1 plan
Mark W Haushill
EVP & CFO · sold 63,314 at avg $58.81
$3.72M
34% of stake
Jun 6, 202510b5-1 plan
Andrew S Robinson
CHAIRMAN & CEO · sold 36,271 at avg $62.65
$2.27M
36% of stake
May 14, 2025No plan
Kirby Hill
Chairman, Captives & Programs · sold 8,249 at $60.87
$502k
50% of stake
May 8, 2025No plan
Mark W Haushill
EVP & CFO · sold 3,447 at $59.23
$204k
1.8% of stake
May 8, 2025No plan
Andrew S Robinson
CHAIRMAN & CEO · sold 13,786 at $59.23
$817k
12% of stake
Mar 17, 202510b5-1 plan
Sean W Duffy
EVP & CHIEF CLAIMS OFFICER · sold 5,625 at $48.90
$275k
39% of stake
Mar 6, 2025No plan
Thomas N Schmitt
CHIEF PEOPLE & ADMIN. OFFICER · sold 3,625 at avg $50.24
$182k
27% of stake
Mar 6, 2025No plan
Leslie Shaunty
GENERAL COUNSEL & SECRETARY · sold 2,240 at avg $50.24
$113k
7.9% of stake
Mar 6, 2025No plan
Kirby Hill
PRESIDENT - INDUSTRY SOLUTIONS · sold 5,269 at avg $50.24
$265k
24% of stake
Mar 6, 2025No plan
Chase M Clark
Chief Underwriting Officer · sold 1,101 at avg $50.24
$55k
25% of stake
Mar 6, 2025No plan
Sandip A Kapadia
EVP, CHIEF ACTUARY · sold 2,961 at avg $50.24
$149k
16% of stake
Mar 6, 2025No plan
Mark W Haushill
EVP & CFO · sold 2,363 at $50.24
$119k
1.3% of stake
Mar 6, 2025No plan
Andrew S Robinson
CHAIRMAN & CEO · sold 20,311 at $50.24
$1.02M
20% of stake
Mar 6, 2025No plan
Sean W Duffy
EVP & CHIEF CLAIMS OFFICER · sold 4,010 at avg $50.24
$201k
22% of stake
Mar 6, 2025No plan
John A Burkhart III
PRESIDENT - SPECIALTY LINES · sold 4,832 at avg $50.24
$243k
18% of stake
Mar 6, 2025No plan
Dan Pk Bodnar
CHIEF INFORMATION OFFICER · sold 3,059 at avg $50.24
$154k
15% of stake
Mar 6, 2025No plan
Gena L Ashe
Director · sold 1,000 at $50.62
$51k
58% of stake
Mar 3, 202510b5-1 plan
Thomas N Schmitt
CHIEF PEOPLE & ADMIN. OFFICER · sold 6,300 at $51.92
$327k
61% of stake
Jan 7, 2025 – Jan 8, 202510b5-1 plan
Andrew S Robinson
CHAIRMAN & CEO · sold 11,274 at avg $45.30
$511k
18% of stake
Jan 2, 2025 – Jan 6, 202510b5-1 plan
Andrew S Robinson
CHAIRMAN & CEO · sold 19,525 at avg $48.26
$942k
23% of stake
Jan 2, 2025 – Jan 6, 202510b5-1 plan
Sandip A Kapadia
EVP, CHIEF ACTUARY · sold 6,484 at avg $48.82
$317k
38% of stake
Jan 3, 2025 – Jan 6, 202510b5-1 plan
Leslie Shaunty
GENERAL COUNSEL & SECRETARY · sold 801 at avg $47.45
$38k
3.8% of stake
Jan 3, 2025 – Jan 6, 202510b5-1 plan
Thomas N Schmitt
CHIEF PEOPLE & ADMIN. OFFICER · sold 1,183 at avg $47.37
$56k
10% of stake
Jan 2, 202510b5-1 plan
Kirby Hill
PRESIDENT - INDUSTRY SOLUTIONS · sold 1,560 at $49.00
$76k
15% of stake
Jan 2, 202510b5-1 plan
Mark W Haushill
EVP & CFO · sold 1,630 at $49.06
$80k
0.9% of stake
Jan 2, 202510b5-1 plan
John A Burkhart III
PRESIDENT - SPECIALTY LINES · sold 1,465 at $49.04
$72k
9.4% of stake
Jan 2, 202510b5-1 plan
Dan Pk Bodnar
CHIEF INFORMATION OFFICER · sold 3,484 at avg $49.72
$173k
22% of stake
Jan 2, 202510b5-1 plan
Sean W Duffy
EVP & CHIEF CLAIMS OFFICER · sold 1,475 at $49.02
$72k
15% of stake
Dec 5, 2024No plan
James Charles Hays
Director · sold 27,950 at $54.84
$1.53M
1.0% of stake

How to read this. Insiders sell for many reasons: taxes, diversifying, a house. Open-market buys are rarer and say more. A 10b5-1 plan is a trading schedule set up months in advance, so those sales were not timed on news. Large holders (funds and 10% owners) are listed under Everything but not counted as insiders. If you own or watch SKWD, we send a push when an executive buys or makes a large sale outside a plan.

Source: SEC Form 4 filings, filed within two business days of each trade and checked for new ones every hour.

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Spot a number that looks wrong? Check it in SKWD's SEC filings or

Download this analysis as a PDF (Pro)

Data sourced from SEC EDGAR filings and third-party price providers. Scores, valuations, and metrics are algorithmic estimates. This is not investment advice. See our Terms and Methodology.

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