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Insider · CIK 0001362369

Stephen Jay Sills

ceopresidentofficerdirector

Files at BOW (Bowhead Specialty Holdings Inc.). First filing -, latest -.

Stephen Jay Sills files SEC Form 4 as CEO, president and director at BOW (Bowhead Specialty Holdings Inc.). No open-market trade is on file; the transactions below are grants, exercises and other rows that carry no view on the price.

A track record needs three past buys with six months of prices behind them; Stephen Jay Sills has 0, so none is measured yet.

Track record
Not enough history
Fewer than three past buys with six months of prices.
Median 6-month excess
-
after past buys, n = 0
Hit rate
-
past buys that beat the index over 6 months
Open-market trades
0 / 0
$0 bought, $0 sold

Signals

This insider’s open-market buys and sells, scored.

No scored open-market trades yet.

Transactions

Every row this insider has filed, 33 in all, newest first.

DateCompanyTransactionSharesPriceValueHoldings afterFiled
May 22, 2026BOW
Bowhead Specialty Holdings Inc.
FTax withholding
Common Stock
-13,053$28.46$371k850,226May 27, 2026
May 22, 2026BOW
Bowhead Specialty Holdings Inc.
FTax withholding
Common Stock
-24,353$28.46$693k838,926May 26, 2026
Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stock
-7,700$0.00$0952,150Mar 13, 2026
Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 1
+1,540$0.00$02,681Mar 13, 2026
Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 2
+1,540$0.00$02,681Mar 13, 2026
Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 3
+1,540$0.00$02,681Mar 13, 2026
Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 4
+1,540$0.00$02,681Mar 13, 2026
Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 5
+1,540$0.00$02,681Mar 13, 2026
Mar 13, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stock
-120,000$0.00$0832,150Mar 13, 2026
Mar 13, 2026BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: Stephen J. Sills 2024 I GRAT #5
+120,000$0.00$0120,000Mar 13, 2026
Feb 19, 2026BOW
Bowhead Specialty Holdings Inc.
AGrant or award
Common Stock
+90,703$0.00$0876,703Feb 23, 2026
Feb 19, 2026BOW
Bowhead Specialty Holdings Inc.
AGrant or award
Common Stock
+88,566$0.00$0965,269Feb 23, 2026
Feb 20, 2026BOW
Bowhead Specialty Holdings Inc.
FTax withholding
Common Stock
-5,419$24.90$135k959,850Feb 23, 2026
Nov 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stock
-75,000$0.00$0786,000Nov 26, 2025
Nov 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Stephen J. Sills 2024 I GRAT #4
+75,000$0.00$075,000Nov 26, 2025
Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stock
-163,185$0.00$0861,000Sep 3, 2025
Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Stephen J. Sills 2024 I GRAT #3
+97,911$0.00$097,911Sep 3, 2025
Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Stephen J. Sills Irrevocable Family GST Exempt Trust
+65,274$0.00$072,000Sep 3, 2025
Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stock
-163,185$0.00$0861,000Sep 2, 2025
Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Stephen J. Sills 2024 I GRAT #3
+97,911$0.00$097,911Sep 2, 2025
Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Stephen J. Sills 2013 IRR Family GST EX
+65,274$0.00$065,274Sep 2, 2025
Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stock
-12,431$0.00$01,024,185Jul 16, 2025
Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 1
+1,141$0.00$01,141Jul 16, 2025
Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 2
+1,141$0.00$01,141Jul 16, 2025
Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 3
+1,141$0.00$01,141Jul 16, 2025
Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 4
+1,141$0.00$01,141Jul 16, 2025
Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Sills Family Trust 5
+1,141$0.00$01,141Jul 16, 2025
Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Stephen J. Sills Irrevocable Family GST Exempt Trust
+6,726$0.00$06,726Jul 16, 2025
May 22, 2025BOW
Bowhead Specialty Holdings Inc.
FTax withholding
Common Stock
-11,921$38.08$454k1,036,616May 23, 2025
May 12, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stock
-72,500$0.00$01,048,537May 16, 2025
May 12, 2025BOW
Bowhead Specialty Holdings Inc.
GGift
Common Stockindirect: By Stephen J. Sills 2024 I Grant #2
+72,500$0.00$072,500May 16, 2025
Feb 21, 2025BOW
Bowhead Specialty Holdings Inc.
AGrant or award
Common Stock
+65,607$0.00$01,053,511Feb 25, 2025
Feb 21, 2025BOW
Bowhead Specialty Holdings Inc.
AGrant or award
Common Stock
+67,526$0.00$01,121,037Feb 25, 2025

Questions about Stephen Jay Sills

Answered from the filings on this page, as of the latest one.

Is Stephen Jay Sills buying or selling?

Stephen Jay Sills has no open-market buy or sell on SEC Form 4; the filings on record are grants, exercises and other transactions.

How did Stephen Jay Sills's past buys perform?

Not measured yet. InsiderTell needs three past buys with six months of prices to publish a track record, and Stephen Jay Sills has 0.

Where does Stephen Jay Sills file Form 4?

Stephen Jay Sills has filed Form 4 at BOW (Bowhead Specialty Holdings Inc.) as CEO and President. A Form 4 is required of officers, directors and holders of more than 10% of a share class within two business days of a trade.

Not investment advice. Scores and forward returns are decision support built from public SEC filings and past prices; they describe what happened after comparable filings, not what will happen after this one. Do your own research and size your risk.

Stephen Jay Sills: insider trades and track record | InsiderTell