MetaCap

Upwork Insider Trades

NASDAQ: UPWKTechnologyEDP ServicesUSD

8.60+0.03 (+0.35%)

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

Last 12 months

Purchases
0 · $0
Sales
36 · $15.04M
Shares bought / sold
0 / 1.02M
Net activity
Net selling $15.0 million

Upwork insider activity

Over the last 12 months, Upwork insiders reported 100 transactions on SEC Form 4: 0 open-market purchases and 36 sales. Insiders bought $0 and sold $15.0 million worth of stock, for net insider selling of $15.0 million. The largest seller was Brown Hayden, with $12.0 million in reported sales.

The most recent filing shows Mekhalfa Sabrina (Chief Accounting Officer) reporting a transaction in 3,578 shares on Sep 18, 2026. Insider sales are common for compensation, tax and diversification reasons, while open-market purchases are rarer; tracking both helps put UPWK's ownership changes in context.

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

UPWK insider transactions

Upwork insider transactions
DateInsiderTypeSharesValueFiling
Sep 18, 2026Brown HaydenPresident & CEOSale23,893$201.92KForm 4
Sep 18, 2026Brown HaydenPresident & CEOOption exercise28,677—Form 4
Sep 18, 2026Brown HaydenPresident & CEOOption exercise17,733—Form 4
Sep 18, 2026Gessert EricaChief Financial OfficerSale9,336$78.90KForm 4
Sep 18, 2026Gessert EricaChief Financial OfficerOption exercise9,700—Form 4
Sep 18, 2026Gessert EricaChief Financial OfficerOption exercise8,433—Form 4
Sep 18, 2026Kappus Anthony RayGM & Chief Operating OfficerSale45,732$386.47KForm 4
Sep 18, 2026Kappus Anthony RayGM & Chief Operating OfficerOption exercise114,860—Form 4
Sep 18, 2026Mekhalfa SabrinaChief Accounting OfficerSale1,299$10.98KForm 4
Sep 18, 2026Mekhalfa SabrinaChief Accounting OfficerOption exercise3,578—Form 4
Aug 18, 2026Kappus Anthony RayGM & Chief Operating OfficerSale1,964$16.55KForm 4
Aug 18, 2026Kappus Anthony RayGM & Chief Operating OfficerOption exercise5,115—Form 4
Aug 18, 2026Brown HaydenPresident & CEOSale50,000$421.36KForm 4
Aug 18, 2026Brown HaydenPresident & CEOSale23,241$195.82KForm 4
Aug 18, 2026Brown HaydenPresident & CEOOption exercise13,639—Form 4
Aug 18, 2026Brown HaydenPresident & CEOOption exercise18,333—Form 4
Aug 18, 2026Brown HaydenPresident & CEOOption exercise14,850—Form 4
Aug 18, 2026Gessert EricaChief Financial OfficerSale22,844$192.48KForm 4
Aug 18, 2026Gessert EricaChief Financial OfficerOption exercise8,524—Form 4
Aug 18, 2026Gessert EricaChief Financial OfficerOption exercise37,500—Form 4
Jul 18, 2026Kappus Anthony RayGM & Chief Operating OfficerSale558$5.05KForm 4
Jul 18, 2026Kappus Anthony RayGM & Chief Operating OfficerOption exercise1,412—Form 4
Jun 18, 2026Brown HaydenPresident & CEOSale23,468$191.28KForm 4
Jun 18, 2026Brown HaydenPresident & CEOOption exercise28,678—Form 4
Jun 18, 2026Brown HaydenPresident & CEOOption exercise17,733—Form 4
Jun 18, 2026Mekhalfa SabrinaChief Accounting OfficerSale1,276$10.40KForm 4
Jun 18, 2026Mekhalfa SabrinaChief Accounting OfficerOption exercise3,577—Form 4
Jun 18, 2026Gessert EricaChief Financial OfficerSale9,169$74.73KForm 4
Jun 18, 2026Gessert EricaChief Financial OfficerOption exercise9,700—Form 4
Jun 18, 2026Gessert EricaChief Financial OfficerOption exercise8,432—Form 4
Jun 4, 2026BRAMLEY CLAIREDirectorAward45,146—Form 4
Jun 4, 2026HARVEY KEVINDirectorAward20,880—Form 4
Jun 4, 2026HARVEY KEVINDirectorAward6,207—Form 4
Jun 4, 2026KELMAN GLENNDirectorAward20,880—Form 4
Jun 4, 2026KELMAN GLENNDirectorAward6,207—Form 4
Jun 4, 2026EVAN DANA LDirectorAward20,880—Form 4
Jun 4, 2026Steele GaryDirectorAward20,880—Form 4
Jun 4, 2026Steele GaryDirectorAward6,207—Form 4
Jun 4, 2026LAYTON THOMASDirectorAward20,880—Form 4
Jun 4, 2026LAYTON THOMASDirectorAward6,772—Form 4
Jun 4, 2026LAYTON THOMASDirectorAward6,207—Form 4
Jun 4, 2026LISSY DAVID HDirectorAward20,880—Form 4
Jun 4, 2026LISSY DAVID HDirectorAward45,146—Form 4
May 18, 2026Brown HaydenPresident & CEOSale50,000$428.48KForm 4
May 18, 2026Brown HaydenPresident & CEOSale22,546$195.33KForm 4
May 18, 2026Brown HaydenPresident & CEOOption exercise13,638—Form 4
May 18, 2026Brown HaydenPresident & CEOOption exercise18,334—Form 4
May 18, 2026Brown HaydenPresident & CEOOption exercise14,850—Form 4
May 18, 2026Gessert EricaChief Financial OfficerSale22,162$192.00KForm 4
May 18, 2026Gessert EricaChief Financial OfficerOption exercise8,524—Form 4
May 18, 2026Gessert EricaChief Financial OfficerOption exercise37,500—Form 4
May 18, 2026Kappus Anthony RayGM & Chief Operating OfficerSale1,905$16.50KForm 4
May 18, 2026Kappus Anthony RayGM & Chief Operating OfficerOption exercise5,114—Form 4
Mar 19, 2026Bottoms DaveGM, MarketplaceSale7,000$80.45KForm 4
Mar 18, 2026Brown HaydenPresident & CEOSale23,745$292.34KForm 4
Mar 18, 2026Brown HaydenPresident & CEOOption exercise28,677—Form 4
Mar 18, 2026Brown HaydenPresident & CEOOption exercise17,733—Form 4
Mar 18, 2026Mekhalfa SabrinaChief Accounting OfficerSale1,482$18.25KForm 4
Mar 18, 2026Mekhalfa SabrinaChief Accounting OfficerOption exercise3,577—Form 4
Mar 18, 2026Bottoms DaveGM, MarketplaceSale11,575$142.51KForm 4
Mar 18, 2026Bottoms DaveGM, MarketplaceOption exercise5,904—Form 4
Mar 18, 2026Bottoms DaveGM, MarketplaceOption exercise6,024—Form 4
Mar 18, 2026Bottoms DaveGM, MarketplaceOption exercise8,980—Form 4
Mar 18, 2026Gessert EricaChief Financial OfficerSale9,278$114.23KForm 4
Mar 18, 2026Gessert EricaChief Financial OfficerOption exercise9,699—Form 4
Mar 18, 2026Gessert EricaChief Financial OfficerOption exercise8,433—Form 4
Feb 19, 2026Bottoms DaveGM, MarketplaceSale15,649$211.44KForm 4
Feb 18, 2026Bottoms DaveGM, MarketplaceSale17,013$234.81KForm 4
Feb 18, 2026Bottoms DaveGM, MarketplaceOption exercise3,750—Form 4
Feb 18, 2026Gessert EricaChief Financial OfficerSale26,292$362.89KForm 4
Feb 18, 2026Gessert EricaChief Financial OfficerOption exercise37,500—Form 4
Feb 18, 2026Brown HaydenPresident & CEOSale50,000$689.30KForm 4
Feb 18, 2026Brown HaydenPresident & CEOSale73,152$1.01MForm 4
Feb 18, 2026Brown HaydenPresident & CEOOption exercise18,333—Form 4
Feb 18, 2026Brown HaydenPresident & CEOOption exercise14,850—Form 4
Feb 18, 2026Brown HaydenPresident & CEOOption exercise7,611—Form 4
Feb 18, 2026Brown HaydenPresident & CEOOption exercise9,589—Form 4
Feb 17, 2026Bottoms DaveGM, MarketplaceOption exercise28,912—Form 4
Feb 17, 2026Gessert EricaChief Financial OfficerOption exercise40,477—Form 4
Feb 17, 2026Brown HaydenPresident & CEOOption exercise127,678—Form 4
Dec 19, 2025Bottoms DaveGM, MarketplaceSale9,622$198.81KForm 4
Dec 18, 2025Bottoms DaveGM, MarketplaceSale11,285$232.34KForm 4
Dec 18, 2025Bottoms DaveGM, MarketplaceOption exercise5,904—Form 4
Dec 18, 2025Bottoms DaveGM, MarketplaceOption exercise6,023—Form 4
Dec 18, 2025Bottoms DaveGM, MarketplaceOption exercise8,980—Form 4
Dec 18, 2025Gessert EricaChief Financial OfficerSale9,044$186.19KForm 4
Dec 18, 2025Gessert EricaChief Financial OfficerOption exercise9,700—Form 4
Dec 18, 2025Gessert EricaChief Financial OfficerOption exercise8,433—Form 4
Dec 18, 2025Brown HaydenPresident & CEOSale23,147$476.55KForm 4
Dec 18, 2025Brown HaydenPresident & CEOOption exercise28,678—Form 4
Dec 18, 2025Brown HaydenPresident & CEOOption exercise17,733—Form 4
Nov 26, 2025Brown HaydenPresident & CEOSale100,000$1.94MForm 4
Nov 26, 2025Brown HaydenPresident & CEOSale175,000$3.40MForm 4
Nov 25, 2025Brown HaydenPresident & CEOSale75,000$1.48MForm 4
Nov 21, 2025Brown HaydenPresident & CEOSale60,000$1.09MForm 4
Nov 21, 2025Steele GaryDirectorSale12,500$218.85KForm 4
Nov 19, 2025Bottoms DaveGM, MarketplaceSale1,748$31.69KForm 4
Nov 18, 2025Brown HaydenPresident & CEOOption exercise14,850—Form 4
Nov 18, 2025Brown HaydenPresident & CEOOption exercise7,610—Form 4
Nov 18, 2025Brown HaydenPresident & CEOOption exercise9,589—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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