๐Ÿ•ต๏ธ Upwork Inc. ($UPWK)

SEC insider & ownership activity, last 12 months ยท CIK 1627475 ยท every row links its SEC filing

Over the last 12 months insiders sold $17.3M with no open-market buying against it. Hayden Brown sold $13.8M (Sepโ€“Aug). No red-flag 8-Ks in the window.

๐Ÿšจ 8 signals active โ€” planned-vs-executed verdicts, pre-event flags, and cluster context live in the API and the alerts bot.
Oct 2025: net +$0 Nov 2025: net -$8.9M Dec 2025: net -$1.1M Jan 2026: net +$0 Feb 2026: net -$2.5M Mar 2026: net -$648K Apr 2026: net +$0 May 2026: net -$832K Jun 2026: net -$276K Jul 2026: net -$5K Aug 2026: net -$826K Sep 2026: net +$0
Monthly net open-market insider flow, last 12 months (up = net buying)

Insider flow

0 buyers, $0 (0 lots) ยท 6 sellers, $17.3M (46 lots)

InsiderBuysBoughtSellsSoldLast
Hayden Brown0โ€“ 19$13.8MAug 18, 2026
Erica Gessert0โ€“ 9$1.6MAug 18, 2026
David Bottoms0โ€“ 12$1.6MMar 19, 2026
Steele Gary0โ€“ 1$219KNov 21, 2025
Kappus Anthony Ray0โ€“ 3$38KAug 18, 2026
Mekhalfa Sabrina0โ€“ 2$29KJun 18, 2026

5%+ holders

HolderStakeClassScheduleEvent
BlackRock, Inc. 15.2% 13GJul 30, 2026 filing โ†—
Quincy J. Lee 6.2% 13GAug 14, 2026 filing โ†—
Vanguard Portfolio Management 6.0% 13GApr 29, 2026 filing โ†—
Ancient ART, L.P. 5.8% 13GAug 14, 2026 filing โ†—
Trango II, L.L.C. 5.8% 13GAug 14, 2026 filing โ†—
Vanguard Capital Management 5.1% 13GApr 30, 2026 filing โ†—
LSV Asset Management 5.0% 13GFeb 5, 2026 filing โ†—

Planned insider sales (Form 144)

SellerPlannedApprox. sale date
Hayden Brown$196KAug 18, 2026 filing โ†—
Erica Gessert$192KAug 18, 2026 filing โ†—
Hayden Brown$410KAug 18, 2026 filing โ†—
Hayden Brown$191KJun 18, 2026 filing โ†—
Erica Gessert$75KJun 18, 2026 filing โ†—
Erica Gessert$192KMay 18, 2026 filing โ†—
Hayden Brown$195KMay 18, 2026 filing โ†—
Hayden Brown$408KMay 18, 2026 filing โ†—
David Bottoms$85KMar 19, 2026 filing โ†—
David Bottoms$143KMar 18, 2026 filing โ†—
Erica Gessert$114KMar 18, 2026 filing โ†—
Hayden Brown$292KMar 18, 2026 filing โ†—
David Bottoms$215KFeb 19, 2026 filing โ†—
Hayden Larson Brown$638KFeb 18, 2026 filing โ†—
Hayden Brown$1.0MFeb 18, 2026 filing โ†—
David Bottoms$236KFeb 18, 2026 filing โ†—
Erica Gessert$363KFeb 18, 2026 filing โ†—
David Bottoms$197KDec 19, 2025 filing โ†—
Erica Gessert$186KDec 18, 2025 filing โ†—
David T. Bottoms$232KDec 18, 2025 filing โ†—
Hayden Brown$477KDec 18, 2025 filing โ†—
Hayden Larson Brown$5.3MNov 26, 2025 filing โ†—
Hayden Larson Brown$1.5MNov 25, 2025 filing โ†—
Gary Steele$219KNov 21, 2025 filing โ†—
Hayden Larson Brown$1.1MNov 21, 2025 filing โ†—
David Bottoms$30KNov 19, 2025 filing โ†—
Erica Gessert$309KNov 18, 2025 filing โ†—
David Bottoms$33KNov 18, 2025 filing โ†—
Hayden Brown$415KNov 18, 2025 filing โ†—
David Bottoms$9KNov 17, 2025 filing โ†—
David Bottoms$196KSep 19, 2025 filing โ†—
Hayden L. Brown$392KSep 19, 2025 filing โ†—
Erica Gessert$167KSep 18, 2025 filing โ†—
Hayden Brown$428KSep 18, 2025 filing โ†—
David Bottoms$209KSep 18, 2025 filing โ†—
Hayden L. Brown$363KSep 18, 2025 filing โ†—

Material events (8-K)

ItemEvent date
Earnings (2.02)Aug 10, 2026 filing โ†—
Financial Statements and Exhibits (9.01)Aug 10, 2026 filing โ†—
Officer/director changes (5.02)Jul 16, 2026 filing โ†—
Material agreement (1.01)Jun 23, 2026 filing โ†—
New financial obligation (2.03)Jun 23, 2026 filing โ†—
Financial Statements and Exhibits (9.01)Jun 23, 2026 filing โ†—
Officer/director changes (5.02)Jun 4, 2026 filing โ†—
Shareholder vote (5.07)Jun 4, 2026 filing โ†—
Earnings (2.02)May 7, 2026 filing โ†—
Exit or disposal costs (2.05)May 7, 2026 filing โ†—
Reg FD disclosure (7.01)May 7, 2026 filing โ†—
Financial Statements and Exhibits (9.01)May 7, 2026 filing โ†—
Officer/director changes (5.02)Mar 12, 2026 filing โ†—
Other events (8.01)Feb 18, 2026 filing โ†—
Earnings (2.02)Feb 3, 2026 filing โ†—
Charter/bylaw changes (5.03)Feb 3, 2026 filing โ†—
Financial Statements and Exhibits (9.01)Feb 3, 2026 filing โ†—
Officer/director changes (5.02)Dec 8, 2025 filing โ†—
Earnings (2.02)Nov 3, 2025 filing โ†—
Financial Statements and Exhibits (9.01)Nov 3, 2025 filing โ†—