undamentalytics Newsletter

Upwork, Inc insider trading

Every open-market purchase and sale by Upwork, Inc's officers, directors and largest shareholders since November 4, 2021, and what the share price did next.

No insider has bought shares on the open market in five years.

Insider purchase Insider sale Marker size reflects trade value. Weekly closes adjusted for splits; may be delayed.
Upwork, Inc insider open-market trades
DateInsiderTrade SharesPriceValue 1M after 3M after 6M after

From insiders' Form 4 filings with the SEC: open-market purchases and sales only (awards, option exercises and shares withheld for tax are excluded), combined to one line per insider per day. "Plan" marks trades the filing says were made under a pre-set Rule 10b5-1 trading plan, which are scheduled in advance. Price changes run from the close on the trade date; hover a figure for the change relative to the S&P 500. Past moves don't predict future ones.

Does following Upwork, Inc’s insiders pay?

From October 5, 2018 to September 22, 2026, 20 insiders reported 5 open-market purchases and 139 sales not made under a pre-set plan in Upwork, Inc. Twelve months after each purchase was reported, the shares were +205.0% against the S&P 500 on average (median +162.2%), over 5 purchases with a full year of prices; 80% beat the index. After sales, the shares moved −0.6% against the index over 12 months (a negative figure means selling was the right call). That rests on fewer than 20 purchases, too few to read much into. Buying each purchase the day after it was reported, an equal amount each, held 12 months or until that insider reported a sale, would have turned $10,000 on March 6, 2020 into $31,516 by November 2, 2026, +18.9% a year. It held shares 37% of the time; the S&P 500 on those same days, with Treasury bills otherwise, made $18,649 (+9.8% a year), and held throughout $27,969 (+16.8%).

$0$25.0k$50.0k$75.0k 2020202120222023202420252026 $31.5k$28.0k$18.6k
Copying Upwork, Inc's insidersS&P 500, same days investedS&P 500, held throughout $10,000 copying every open-market purchase by Upwork, Inc's insiders from March 6, 2020, before costs and taxes, marked weekly. Uninvested money earns the Treasury bill rate; the portfolio held shares 37% of the time.
Upwork, Inc: each insider's record
InsiderRolePurchases12 months after their purchasesBeat the S&P 500Sales12 months after their salesLatest report
Brown Hayden President & CEO 0 — — 56 +20.9% (49) September 22, 2026
Gessert Erica Chief Financial Officer 0 — — 20 −14.9% (12) September 22, 2026
Marie Olivier Chief Accounting Officer 0 — — 13 −13.6% (13) June 23, 2025
Gilpin Eric Chief Sales Officer 0 — — 10 −18.1% (10) February 22, 2023
Mccombs Jeff Chief Financial Officer 0 — — 8 −41.5% (8) November 22, 2022
Bottoms Dave GM, Marketplace 0 — — 6 −17.6% (6) August 20, 2025
Nelson Elizabeth A Director 0 — — 5 −37.3% (5) May 14, 2025
Layton Thomas Director 1 +397.7% (1) 100% 3 −63.0% (3) May 15, 2025
Gretsch Gregory C. Director 3 +227.7% (3) 100% 0 — August 11, 2020
Kappus Anthony Ray GM & Chief Operating Officer 0 — — 3 — September 22, 2026
Mekhalfa Sabrina Chief Accounting Officer 0 — — 3 — September 22, 2026
Srinivasan Leela Director 0 — — 3 +22.5% (3) June 6, 2022
Steele Gary Director 0 — — 3 −34.2% (2) November 25, 2025
Balkanski Alexandre 10% owner 0 — — 1 −22.9% (1) August 12, 2019
Dunlevie Bruce 10% owner 0 — — 1 −19.1% (1) August 13, 2019
Goldfarb Andrew P 10% owner 0 — — 1 −61.1% (1) April 3, 2019
Harvey Kevin Director 1 −55.7% (1) 0% 0 — May 16, 2022
Kinion Brian K Chief Financial Officer 0 — — 1 +398.6% (1) March 3, 2020
Marriott Dan Director 0 — — 1 −22.9% (1) August 12, 2019
Spurlock Steven M 10% owner 0 — — 1 −14.5% (1) August 20, 2019

Moves are the shares’ return including dividends minus the S&P 500’s, from the close on the first trading day after each report; the number of trades with a finished 12-month window is in brackets. Green means the trade went the insider’s way (a purchase ahead of the index, a sale followed by the shares trailing it). A trade reported both by a director or officer and by a fund or company they are linked to counts once here, under the person. Purchases count only where the share price actually traded was at least $5. These figures describe what the shares did, not why anyone traded. Insiders across all companies.

When several insiders traded Upwork, Inc

Months when 2 or more insiders became net buyers, or 3 or more net sellers, of Upwork, Inc in reports dated in the 91 days before the month end, and how the stock did against the S&P 500 from that month end. After 8 selling crowds, −2.4%. One company's history is too short to judge by; the test across every company is the better guide.

MonthCrowd3 months on, vs S&P 5006 months12 months
March 31, 20263 selling−32.7%−43.4%not yet
November 28, 20253 selling−33.3%−66.3%not yet
May 30, 20254 selling−10.4%+10.8%−72.4%
May 31, 20244 selling−16.0%+45.6%+29.8%
December 29, 20233 selling−27.9%−44.0%−14.9%
May 28, 20214 selling−13.6%−30.1%−59.8%
May 29, 20203 selling+3.4%+155.8%+238.1%
August 30, 20195 selling−27.4%−47.9%−16.5%

Colours show whether the crowd was right: green when buyers were followed by a rise above the index, or sellers by a fall below it. Total returns from the month end; past patterns are not a forecast.

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