Stephen Jay Sills

CIK 1362369 · CEO and President · last filed 2026-05-27

Stephen Jay Sills is a CEO and President who has filed 19 SEC Form 4 insider transactions across 2 companies since 2007. The most recent filing shows the insider had shares withheld for taxes covering $371.5K of BOW on May 27, 2026. Across all open-market trades the lifetime net is +$1.0M, making them a net buyer over the disclosed history. Current disclosed insider exposure totals $30.5M across reported positions.

"Disclosed insider exposure" sums this person's most-recently-reported share counts across each company they're an insider in, multiplied by the current underlying price. It is not net worth — it misses retail holdings, private investments, real estate, index funds, and any company where the person isn't an SEC-reporting insider. For informational purposes only.

Disclosed Exposure

$30.48M

Companies

Total Filings

Lifetime Open-Market Net

$1.00M

Charts

Trading activity, where the exposure sits, and each trade against the stock price.

BOW price and trades

Daily close with each Form 4 filing on this company marked: green = open-market buy, red = open-market sale, purple = grants, exercises, gifts and other non-market transactions. Marker size scales with the dollar value.

Shares held

Shares owned after each reported transaction on this company (direct holdings as reported).

Open-market buying and selling

by month

Dollar value of open-market purchases (code P, up) and sales (code S, down) across all companies, by filing month. Grants, exercises and gifts are excluded.

Exposure by company

latest

OfficerDirector10% owner* stale (no filing in 3 yrs)

Most recently reported shares × current price. Faded bars (*) have had no filing in 3 years, so the person may no longer hold them. Click a bar to chart that company.

Filer Profile

Reported Address

C/O BOWHEAD SPECIALTY HOLDINGS INC.
452 FIFTH AVENUE
NEW YORK, NY 10018

Profile details as reported on the filer's SEC submissions — for individual insiders the address is often in care of the issuer. Related filers are identified from jointly filed SEC submissions and shared reported addresses. View filings on SEC EDGAR.

Holdings By Company

Latest on-record share count from this person's most recent non-derivative Form 4 transaction in each company. Disclosed exposure = shares × current underlying price.

Symbol	Role	Shares	Price	Disclosed Exposure	Lifetime OM Net	Filings	Latest Filed
BOW	CEO and President	891,597	$34.19	$30.48M	$1.00M	12	2026-05-27
Darwin Professional Underwriters Inc (DR) Delisted	President and CEO	0	—	—	$0	6	2008-10-21

Recent Filings

19 filings

Insider activity across all companies, newest first. Form 4 rows are post-trade confirmations (buys, sells, grants, exercises). Notice (144) rows are pre-trade notices of intent to sell restricted or control stock under Rule 144 — they may not all execute. Compare adjacent dates to see which notices became actual sales.

Filed	Symbol	Action	Net Shares	Net $	Link
2026-05-27	BOW	Tax (F)	−13,053	-$371.5K	EDGAR
2026-05-26	BOW	Tax (F)	−24,353	-$693.1K	EDGAR
2026-03-13	BOW	Gift (G)	—	$0	EDGAR
2026-02-23	BOW	Mixed	+173,850	-$134.9K	EDGAR
2025-11-26	BOW	Gift (G)	—	$0	EDGAR
2025-09-03	BOW	Gift (G)	—	$0	EDGAR
2025-09-02	BOW	Gift (G)	—	$0	EDGAR
2025-07-16	BOW	Gift (G)	—	$0	EDGAR
2025-05-23	BOW	Tax (F)	−11,921	-$454.0K	EDGAR
2025-05-16	BOW	Gift (G)	—	$0	EDGAR

Showing 1–10 of 19

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Form 4 codes: P = open-market purchase · S = open-market sale · A = grant/award · M = option exercise · F = tax withholding at vest · G = bona-fide gift · D = disposition to issuer · J = other (see filing footnote). Only P / S codes carry directional signal.
Notice (144 / 144/A): Form 144 is a notice of intent to sell restricted/control stock under Rule 144, filed before the sale; 144/A is an amendment. Many notices are pre-scheduled under Rule 10b5-1 plans. A Form 4 with code S typically follows within a few days when the planned sale executes; missing follow-up Form 4s suggest the notice was cancelled or modified.