greeksoup/ stock research
Stock research / United States / UPWK / Planned sales

Upwork, Inc. planned insider sales

In the twelve months since 11 October 2025 insiders at Upwork, Inc. filed 33 Form 144 notices of planned sales, 1.1 million shares worth $15.7 million at the time of filing, from 7 sellers. The latest, filed 18 September 2026: Erica Gessert (officer), 9,336 shares worth $78,898, planned for around 18 September 2026 through Morgan Stanley Smith Barney LLC Executive Financial Services.

FiledSellerRelationshipSharesValuePlanned saleBrokerHow acquiredFiling
18 September 2026Erica GessertOfficer9,336$78,89818 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 September 2026Hayden BrownOfficer, Director23,893$201,91718 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 September 2026Anthony KappusOfficer45,732$386,47718 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 August 2026Erica GessertOfficer22,844$192,47718 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 August 2026Hayden BrownOfficer, Director23,241$195,82218 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
18 August 2026Hayden BrownDirector, Officer50,000$409,50018 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRSU/PSUForm 144
18 June 2026Erica GessertOfficer9,169$74,73418 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 June 2026Hayden BrownOfficer, Director23,468$191,28118 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 May 2026Erica GessertOfficer22,162$191,99818 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 May 2026Hayden BrownOfficer, Director22,546$195,32518 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
18 May 2026Hayden BrownDirector, Officer50,000$408,50018 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted stock units and Performance stock unitsForm 144
19 March 2026David BottomsOfficer7,000$84,63019 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted Stock UnitsForm 144
18 March 2026Erica GessertOfficer9,278$114,22918 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 March 2026David BottomsOfficer11,575$142,50918 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 March 2026Hayden BrownOfficer, Director23,745$292,34418 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
19 February 2026David BottomsOfficer15,649$214,86119 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Stock Units; Restricted Stock UnitsForm 144
18 February 2026David BottomsOfficer17,013$236,42318 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
18 February 2026Erica GessertOfficer26,292$363,37718 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
18 February 2026Hayden Larson BrownDirector, Officer50,000$638,00018 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRSU/PSUForm 144
18 February 2026Hayden BrownOfficer, Director73,152$1.0 million18 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
19 December 2025David BottomsOfficer9,622$196,96219 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted Stock UnitsForm 144
18 December 2025Erica GessertOfficer9,044$186,19718 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 December 2025David T. BottomsOfficer11,285$232,33418 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 December 2025Hayden BrownOfficer, Director23,147$476,54818 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
26 November 2025Hayden Larson BrownOfficer275,000$5.3 million26 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPreviously Exercised OptionsForm 144
25 November 2025Hayden Larson BrownOfficer75,000$1.5 million25 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPreviously Exercised OptionsForm 144
21 November 2025Gary SteeleOfficer12,500$218,84921 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted stock vesting under a registered planForm 144
21 November 2025Hayden Larson BrownOfficer60,000$1.1 million21 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPreviously Exercised OptionsForm 144
19 November 2025David BottomsOfficer1,748$29,85619 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted Stock UnitsForm 144
18 November 2025David BottomsOfficer2,002$33,43718 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 November 2025Erica GessertOfficer18,493$308,86518 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 November 2025Hayden BrownOfficer, Director24,846$414,97018 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
17 November 2025David BottomsOfficer561$9,24517 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesEmployee Stock Purchase PlanForm 144
A Form 144 is the notice an insider files with the SEC before selling restricted or control shares over the Rule 144 thresholds; it says what may be sold, not what was.
Read moreValue is the filer's own aggregate market value. Whether the sale happened shows up later on Form 4, on the insiders page.

Source

Form 144 filings on EDGAR for Upwork, Inc.: the company's filing index, each notice read from its own XML.

The same record on your computer

GreekSoup is also a free program for your own computer. It reads these same filings for the names you follow, refreshed as they land, with no account. One pasted line installs it.

Install