MetaCap

Skyward Specialty Insurance Group Insider Trades

NASDAQ: SKWDFinanceProperty-Casualty InsurersUSD

58.32-0.99 (-1.67%)

At close: Oct 9, 4:00 PM ET · Delayed 15 min

Last 12 months

Purchases
11 · $1.53M
Sales
5 · $579.04K
Shares bought / sold
32.50K / 11.75K
Net activity
Net buying $948,678

Skyward Specialty Insurance Group insider activity

Over the last 12 months, Skyward Specialty Insurance Group insiders reported 64 transactions on SEC Form 4: 11 open-market purchases and 5 sales. Insiders bought $1.5 million and sold $579,036 worth of stock, for net insider buying of $948,678. The largest seller was Schmitt Thomas N, with $544,737 in reported sales.

The most recent filing shows Schmitt Thomas N (CPO, Skyward Group) selling 8,397 shares at $51.32 on Jun 12, 2026. Insider sales are common for compensation, tax and diversification reasons, while open-market purchases are rarer; tracking both helps put SKWD's ownership changes in context.

Summary generated from market data by MetaCap's automated system. Methodology

SKWD insider transactions

Skyward Specialty Insurance Group insider transactions
DateInsiderTypeSharesValueFiling
Jun 12, 2026Schmitt Thomas NCPO, Skyward GroupSale8,397$430.96KForm 4
May 21, 2026Kuczinski Anthony JDirectorBuy1,000$47.20KForm 4
May 21, 2026Kuczinski Anthony JDirectorBuy800$37.60KForm 4
May 21, 2026Kuczinski Anthony JDirectorBuy200$9.40KForm 4
May 11, 2026Ashe Gena LDirectorSale500$23.18KForm 4
May 11, 2026Ashe Gena LDirectorSale140$6.49KForm 4
May 11, 2026Ashe Gena LDirectorSale100$4.63KForm 4
May 11, 2026Ashe Gena LDirectorOption exercise1,797—Form 4
May 7, 2026Kuczinski Anthony JDirectorOption exercise1,797—Form 4
May 6, 2026Duffy Sean WEVP & Chief Claims OfficerTax withholding1,671$72.99KForm 4
May 6, 2026Duffy Sean WEVP & Chief Claims OfficerOption exercise3,805—Form 4
May 6, 2026Robinson Andrew SChairman & CEO, Skyward GroupTax withholding7,930$346.38KForm 4
May 6, 2026Robinson Andrew SChairman & CEO, Skyward GroupOption exercise20,150—Form 4
May 6, 2026Burkhart John A IIIPresident, US P&CTax withholding1,894$82.73KForm 4
May 6, 2026Burkhart John A IIIPresident, US P&COption exercise4,813—Form 4
May 6, 2026Schmitt Thomas NCPO, Skyward GroupTax withholding1,322$57.74KForm 4
May 6, 2026Schmitt Thomas NCPO, Skyward GroupOption exercise3,358—Form 4
May 6, 2026HAUSHILL MARK WCFO - Skyward GroupTax withholding1,982$86.57KForm 4
May 6, 2026HAUSHILL MARK WCFO - Skyward GroupOption exercise5,036—Form 4
May 6, 2026Bodnar Dan PKChief Information OfficerTax withholding1,004$43.85KForm 4
May 6, 2026Bodnar Dan PKChief Information OfficerOption exercise2,686—Form 4
May 6, 2026Kapadia Sandip AHead of ActuarialTax withholding1,374$60.02KForm 4
May 6, 2026Kapadia Sandip AHead of ActuarialOption exercise2,686—Form 4
May 5, 2026Creager Robert E.DirectorOption exercise1,797—Form 4
May 5, 2026Hays James CharlesDirectorOption exercise1,797—Form 4
Mar 3, 2026Kuczinski Anthony JDirectorBuy1,000$48.13KForm 4
Mar 2, 2026Peirce Christopher LockeDirectorBuy3,200$151.36KForm 4
Mar 2, 2026Kuczinski Anthony JDirectorBuy2,000$97.58KForm 4
Feb 27, 2026Robinson Andrew SChairman & CEO, Skyward GroupBuy11,279$529.44KForm 4
Feb 27, 2026Robinson Andrew SChairman & CEO, Skyward GroupBuy10,821$503.93KForm 4
Feb 27, 2026McHarg Taryn LeonieCFO - ApolloBuy100$4.65KForm 4
Feb 27, 2026McHarg Taryn LeonieCFO - ApolloBuy100$4.67KForm 4
Feb 27, 2026Kuczinski Anthony JDirectorBuy2,000$93.75KForm 4
Feb 26, 2026HAUSHILL MARK WEVP & CFO, Skyward GroupTax withholding1,436$65.90KForm 4
Feb 26, 2026Schmitt Thomas NCPO, Skyward GroupTax withholding1,153$52.91KForm 4
Feb 26, 2026Robinson Andrew SChairman & CEO, Skyward GroupTax withholding6,916$317.38KForm 4
Feb 26, 2026Burkhart John A IIIPresident, US P&CTax withholding1,652$75.81KForm 4
Feb 26, 2026Bodnar Dan PKChief Information OfficerTax withholding876$40.20KForm 4
Feb 26, 2026Kapadia Sandip AHead of ActuarialTax withholding847$38.87KForm 4
Feb 26, 2026Duffy Sean WEVP & Chief Claims OfficerTax withholding1,391$63.83KForm 4
Feb 25, 2026HAUSHILL MARK WEVP & CFO, Skyward GroupOption exercise4,392—Form 4
Feb 25, 2026Schmitt Thomas NCPO, Skyward GroupOption exercise2,929—Form 4
Feb 25, 2026Robinson Andrew SChairman & CEO, Skyward GroupOption exercise17,575—Form 4
Feb 25, 2026Burkhart John A IIIPresident, US P&COption exercise4,198—Form 4
Feb 25, 2026Bodnar Dan PKChief Information OfficerOption exercise2,343—Form 4
Feb 25, 2026Kapadia Sandip AHead of ActuarialOption exercise2,343—Form 4
Feb 25, 2026Duffy Sean WEVP & Chief Claims OfficerOption exercise3,318—Form 4
Feb 9, 2026Schmitt Thomas NCPO, Skyward GroupSale2,616$113.77KForm 4
Jan 12, 2026Burkhart John A IIIPresident, US P&C, Skyward GrpTax withholding2,623$120.92KForm 4
Jan 12, 2026Burkhart John A IIIPresident, US P&C, Skyward GrpOption exercise6,665—Form 4
Jan 12, 2026Burkhart John A IIIPresident, US P&C, Skyward GrpTax withholding2,798$128.99KForm 4
Jan 12, 2026Burkhart John A IIIPresident, US P&C, Skyward GrpOption exercise6,665—Form 4
Jan 12, 2026Kapadia Sandip AHead of ActuarialTax withholding1,808$83.35KForm 4
Jan 12, 2026Kapadia Sandip AHead of ActuarialOption exercise5,000—Form 4
Jan 12, 2026Kapadia Sandip AHead of ActuarialTax withholding1,985$91.51KForm 4
Jan 12, 2026Kapadia Sandip AHead of ActuarialOption exercise5,000—Form 4
Jan 12, 2026Duffy Sean WEVP & Chief Claims OfficerTax withholding2,095$96.58KForm 4
Jan 12, 2026Duffy Sean WEVP & Chief Claims OfficerOption exercise5,000—Form 4
Jan 12, 2026Duffy Sean WEVP & Chief Claims OfficerTax withholding2,276$104.92KForm 4
Jan 12, 2026Duffy Sean WEVP & Chief Claims OfficerOption exercise5,000—Form 4
Jan 12, 2026Schmitt Thomas NCPO, Skyward GroupTax withholding1,968$90.72KForm 4
Jan 12, 2026Schmitt Thomas NCPO, Skyward GroupOption exercise5,000—Form 4
Jan 12, 2026Schmitt Thomas NCPO, Skyward GroupTax withholding2,149$99.07KForm 4
Jan 12, 2026Schmitt Thomas NCPO, Skyward GroupOption exercise5,000—Form 4

Transaction codes follow SEC Form 4: P = open-market purchase, S = open-market sale, A = grant or award, M = option exercise, F = shares withheld for taxes. About Form 4

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