Skyward Specialty Insurance SKWD Insider Ownership

NASDAQ SKWD

$60.79 -0.88 (-1.43%)

As of: Oct 21, 2026 · 11:03 AM EDT

Insider Holdings by Owner

3.08Mn Shares

Insider Ownership Statistics

as of 30 Sep, 2026

Insider Ownership

8.56%

■0% pp QoQ

Shares Held by Insiders

3.81Mn

filed for Sep 2026

■0.00% QoQ

Shares Outstanding

44.52Mn

44,521,162 shares

Direct Holdings

1.07Mn

Indirect: 2.74Mn

Net Shares Traded (QoQ)

no net change in Sep 2026

Insiders Holding Shares

with Form 4 holdings on file

Shares Owned by Insiders

Shares held % of outstanding

Latest —

Average ownership —

Peak ownership —

Shares Purchased/Sold by Insiders

Bought Sold

Latest quarter —

Net over range —

Buying quarters —

Insider Ownership Summary

Updated Oct 10, 2026

Over the past 12 months, Skyward Specialty Insurance insiders bought $1.53 million of stock on the open market (32.5K shares) and sold $969,133 (19.56K shares).

A count shows 4 insiders buying SKWD stock on the open market over the past 12 months and 3 insiders selling.
Among Skyward Specialty Insurance's insiders, the largest open-market purchases in the past 12 months were by Andrew S. Robinson (Chairman & CEO, Skyward Group), totaling $1.03 million (22.1K shares), most recently on February 27, 2026.
Conversely, Thomas N. Schmitt (CPO, Skyward Group) was SKWD's largest open-market seller in the past 12 months, with $548,927 of sales (11.1K shares); the latest was on June 12, 2026.
Outside the open market, Skyward Specialty Insurance insiders received 566.2K shares in stock awards, acquired 233.29K shares through option exercises and conversions and gave up 108.08K shares to cover taxes or exercise prices over the past 12 months.
According to Business Quant data, insiders at Skyward Specialty Insurance reported 3.81Mn shares in total in their latest Form 4 filings, unchanged from 3.81Mn shares at the end of Q2 2026.
Direct holdings account for 1.07Mn shares (28.19%) of SKWD's insider total, and indirect holdings through trusts, partnerships and family members for 2.74Mn shares (71.81%).
Per Business Quant, 21 insiders of SKWD hold shares, counting officers, directors and 10% owners who have filed a Form 4 in the past two years.
Skyward Specialty Insurance's three largest insider shareholders, based on their latest Form 4 filings, are James Charles Hays (Director, 2.82Mn shares), David Christopher Ben Ibeson (CEO & Apollo, 346.57K shares) and Andrew S. Robinson (Chairman & CEO, Skyward Group, 179.89K shares).
James Charles Hays holds 73.99% of the combined insider position in Skyward Specialty Insurance.
Institutions accounted for 88.70% of SKWD's outstanding shares in Q2 2026, insiders about 8.56% per their latest Form 4 filings, and other investors, including the public, about 2.74%.
A total of 57 Form 4 filings with transactions in Skyward Specialty Insurance stock were made over the past 12 months, by 21 insiders.
Insider figures for SKWD include Form 4 filings through August 7, 2026.

Form 4 Holdings

Insiders Holding SKWD

Insiders 22

Shares held 3.08Mn

Of outstanding 6.92%

#	Insider	Position	Direct	Indirect	Total	Share of Insiders	Last Filed
1	Corp Westaim	TenPercentOwner	1,919,639	0	1,919,639	62.3%	13 May, 2024
2	David Christopher Ben Ibeson	Ceo Apollo	266,867	79,708	346,575	11.3%	05 Jan, 2026
3	Andrew S Robinson	Chairman Ceo, Skyward Group	179,894	0	179,894	5.8%	08 May, 2026
4	James Charles Hays	Director	175,858	0	175,858	5.7%	07 May, 2026
5	Mark W Haushill	Cfo Skyward Group	139,466	0	139,466	4.5%	08 May, 2026
6	James Richard Slaughter	Cuo Apollo	55,475	12,724	68,199	2.2%	05 Jan, 2026
7	Robert E. Creager	Director	54,830	0	54,830	1.8%	07 May, 2026
8	John A Iii Burkhart	President, Us Pc	37,736	0	37,736	1.2%	08 May, 2026
9	Dan Pk Bodnar	Chief Information Officer	28,147	0	28,147	0.9%	08 May, 2026
10	Leslie Shaunty	General Counsel Secretary	26,104	0	26,104	0.8%	10 Mar, 2025
11	Sean W Duffy	Evp Chief Claims Officer	20,097	0	20,097	0.7%	08 May, 2026
12	Sandip A Kapadia	Head Of Actuarial	18,353	0	18,353	0.6%	08 May, 2026
13	Anthony J Kuczinski	Director	15,977	0	15,977	0.5%	21 May, 2026
14	Thomas N Schmitt	Cpo, Skyward Group	10,353	0	10,353	0.3%	15 Jun, 2026
15	Marcia A Dall	Director	8,433	0	8,433	0.3%	09 May, 2025
16	Kirby Hill	Chairman, Captives Programs	8,249	0	8,249	0.3%	15 May, 2025
17	Katharine Terry	Director	6,780	0	6,780	0.2%	09 May, 2025
18	Gena L Ashe	Director	4,570	0	4,570	0.1%	12 May, 2026
19	Michael J. Morrissey	Director	3,519	0	3,519	0.1%	09 May, 2025
20	Chase M Clark	Chief Underwriting Officer	3,279	0	3,279	0.1%	10 Mar, 2025
21	Christopher Locke Peirce	Director	3,200	0	3,200	0.1%	03 Mar, 2026
22	Taryn Leonie Mcharg	Cfo Apollo	0	100	100	0.0%	03 Mar, 2026

Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.

Form 4 Filings

490 Insider Transactions

Source SEC Form 4

Latest quarter Sep 2026

Date	Insider	Position	Transaction	Shares	Price	Value	Shares Held After	Ownership
06 Aug, 2026	Peter C Hearn	Director	Acquired A	1,845	$0.00	$0	1,845	Direct
12 Jun, 2026	Thomas N Schmitt	Cpo, Skyward Group	Disposed S	8,397	$51.32	$430.96K	10,353	Direct
21 May, 2026	Anthony J Kuczinski	Director	Acquired P	200	$47.00	$9.40K	14,177	Direct
21 May, 2026	Anthony J Kuczinski	Director	Acquired P	800	$47.00	$37.60K	14,977	Direct
21 May, 2026	Anthony J Kuczinski	Director	Acquired P	1,000	$47.20	$47.20K	15,977	Direct
11 May, 2026	Gena L Ashe	Director	Acquired M	1,797	—	—	5,310	Direct
11 May, 2026	Gena L Ashe	Director	Disposed S	100	$46.35	$4.64K	5,210	Direct
11 May, 2026	Gena L Ashe	Director	Disposed S	140	$46.35	$6.49K	5,070	Direct
11 May, 2026	Gena L Ashe	Director	Disposed S	500	$46.35	$23.18K	4,570	Direct
11 May, 2026	Gena L Ashe	Director	Disposed M	1,797	$0.00	$0	0	Direct
07 May, 2026	Anthony J Kuczinski	Director	Acquired M	1,797	—	—	13,977	Direct
06 May, 2026	Mark W Haushill	Cfo Skyward Group	Acquired M	5,036	$0.00	$0	141,448	Direct
06 May, 2026	Dan Pk Bodnar	Chief Information Officer	Acquired M	2,686	$0.00	$0	29,151	Direct
06 May, 2026	John A Iii Burkhart	President, Us Pc	Acquired M	4,813	$0.00	$0	39,630	Direct
06 May, 2026	Andrew S Robinson	Chairman Ceo, Skyward Group	Acquired M	20,150	$0.00	$0	187,824	Direct
06 May, 2026	Sandip A Kapadia	Head Of Actuarial	Acquired M	2,686	$0.00	$0	19,727	Direct
06 May, 2026	Sean W Duffy	Evp Chief Claims Officer	Acquired M	3,805	$0.00	$0	21,768	Direct
06 May, 2026	Thomas N Schmitt	Cpo, Skyward Group	Acquired M	3,358	$0.00	$0	19,881	Direct
06 May, 2026	Andrew S Robinson	Chairman Ceo, Skyward Group	Disposed F	7,930	$43.68	$346.38K	179,894	Direct
06 May, 2026	Mark W Haushill	Cfo Skyward Group	Disposed F	1,982	$43.68	$86.57K	139,466	Direct

Showing 1 to 20 of 490 transactions