UPWK · Insider Trading
Upwork Inc. Common Stock
Every open-market purchase and sale reported by UPWK officers, directors and 10%+ beneficial owners on SEC Form 4, which must be filed within two business days of the transaction. Sales often reflect scheduled 10b5-1 plans or tax withholding rather than a directional view, so read counts alongside the size and the filer.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-10-20 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | +854 | −$4.71K |
| 2026-09-22 | Sabrina Mekhalfa | Chief Accounting Officer | MIXED | +2,279 | −$10.98K |
| 2026-09-22 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | +69,128 | −$386.47K |
| 2026-09-22 | Hayden Brown | President & CEO | MIXED | +22,517 | −$201.92K |
| 2026-09-22 | Erica Gessert | Chief Financial Officer | MIXED | +8,797 | −$78.90K |
| 2026-08-20 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | +3,151 | −$16.55K |
| 2026-08-20 | Hayden Brown | President & CEO | MIXED | −26,419 | −$617.18K |
| 2026-08-20 | Erica Gessert | Chief Financial Officer | MIXED | +23,180 | −$192.48K |
| 2026-07-21 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | +854 | −$5.05K |
| 2026-06-23 | Hayden Brown | President & CEO | MIXED | +22,943 | −$191.28K |
| 2026-06-23 | Sabrina Mekhalfa | Chief Accounting Officer | MIXED | +2,301 | −$10.40K |
| 2026-06-23 | Erica Gessert | Chief Financial Officer | MIXED | +8,963 | −$74.73K |
| 2026-06-08 | Dana L Evan | Director | A | +20,880 | — |
| 2026-06-08 | Kevin Harvey | Director | A | +27,087 | — |
| 2026-06-08 | David H Lissy | Director | A | +66,026 | — |
| 2026-06-08 | Glenn Kelman | Director | A | +27,087 | — |
| 2026-06-08 | Thomas Layton | Director | A | +33,859 | — |
| 2026-06-08 | Claire Bramley | Director | A | +45,146 | — |
| 2026-06-08 | Gary Steele | Director | A | +27,087 | — |
| 2026-05-20 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | +3,209 | −$16.50K |
| 2026-05-20 | Hayden Brown | President & CEO | MIXED | −25,724 | −$623.80K |
| 2026-05-20 | Erica Gessert | Chief Financial Officer | MIXED | +23,862 | −$192.00K |
| 2026-04-21 | Anthony Ray Kappus | GM & Chief Operating Officer | A | +22,603 deriv. | — |
| 2026-03-20 | Sabrina Mekhalfa | Chief Accounting Officer | MIXED | +2,095 | −$18.25K |
| 2026-03-20 | Hayden Brown | President & CEO | MIXED | +22,665 | −$292.34K |
| 2026-03-20 | Erica Gessert | Chief Financial Officer | MIXED | +8,854 | −$114.23K |
| 2026-03-20 | Dave Bottoms | GM, Marketplace | MIXED | +2,333 | −$222.96K |
| 2026-02-19 | Erica Gessert | Chief Financial Officer | MIXED | +51,685 | −$362.89K |
| 2026-02-19 | Dave Bottoms | GM, Marketplace | MIXED | — | −$446.25K |
| 2026-02-19 | Hayden Brown | President & CEO | MIXED | +54,909 | −$1.70M |
| 2025-12-22 | Erica Gessert | Chief Financial Officer | MIXED | +9,089 | −$186.19K |
| 2025-12-22 | Dave Bottoms | GM, Marketplace | MIXED | — | −$431.14K |
| 2025-12-22 | Sabrina Mekhalfa | Chief Accounting Officer | A | +42,929 deriv. | — |
| 2025-12-22 | Hayden Brown | President & CEO | MIXED | +23,264 | −$476.55K |
| 2025-11-28 | Hayden Brown | President & CEO | Sell | −350,000 | −$6.83M |
| 2025-11-25 | Hayden Brown | President & CEO | Sell | −60,000 | −$1.09M |
| 2025-11-25 | Gary Steele | Director | Sell | −12,500 | −$218.85K |
| 2025-11-20 | Hayden Brown | President & CEO | MIXED | +25,536 | −$415.01K |
| 2025-11-20 | Erica Gessert | Chief Financial Officer | MIXED | +19,007 | −$308.84K |
| 2025-11-19 | Dave Bottoms | GM, Marketplace | MIXED | −561 | −$74.38K |
| 2025-09-22 | Dave Bottoms | GM, Marketplace | MIXED | — | −$408.65K |
| 2025-09-22 | Erica Gessert | Chief Financial Officer | MIXED | +9,403 | −$167.30K |
| 2025-09-19 | Hayden Brown | President & CEO | MIXED | −35,933 | −$1.57M |
| 2025-09-03 | Dave Bottoms | GM, Marketplace | Sell | −1,690 | −$25.27K |
| 2025-08-21 | Olivier Marie | Chief Accounting Officer | Sell | −1,686 | −$23.41K |
| 2025-08-20 | Dave Bottoms | GM, Marketplace | MIXED | +1,690 | −$28.50K |
| 2025-08-20 | Erica Gessert | Chief Financial Officer | MIXED | +18,464 | −$263.37K |
| 2025-08-19 | Hayden Brown | President & CEO | MIXED | −35,194 | −$1.18M |
| 2025-08-18 | Olivier Marie | Chief Accounting Officer | MIXED | +392 | −$31.14K |
| 2025-08-12 | Dave Bottoms | GM, Marketplace | Sell | −9,000 | −$115.94K |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| Kevin Harvey | Director | 1,898,531 | $16.61M |
| Thomas Layton | Director | 1,691,430 | $14.80M |
| Hayden Brown | President & CEO | 793,593 | $6.94M |
| Erica Gessert | Chief Financial Officer | 373,222 | $3.27M |
| Elizabeth A Nelson | Director | 373,011 | $3.26M |
| Gary Steele | Director | 112,216 | $981.89K |
| Anilu Vazquez-Ubarri | Director | 83,968 | $734.72K |
| Leela Srinivasan | Director | 82,783 | $724.35K |
| Anthony Ray Kappus | GM & Chief Operating Officer | 77,755 | $680.36K |
| Glenn Kelman | Director | 66,422 | $581.19K |
| David H Lissy | Director | 66,026 | $577.73K |
| Dana L Evan | Director | 56,835 | $497.31K |
| Claire Bramley | Director | 45,146 | $395.03K |
| Dave Bottoms | GM, Marketplace | 21,253 | $185.96K |
| Sabrina Mekhalfa | Chief Accounting Officer | 7,974 | $69.77K |
| Olivier Marie | Chief Accounting Officer | 748 | $6.54K |
Form 4 reports a change in beneficial ownership by an officer, director or 10%+ holder, and must be filed within two business days of the transaction — so this is close to real time, unlike the 45-day-lagged 13F institutional data.
Transaction codes matter more than the raw buy/sell count. Code P is an open-market purchase — an insider choosing to buy with their own money, which is the signal most research treats as informative. Code S is a sale, but sales are frequently pre-scheduled under a 10b5-1 plan or cover tax withholding on vesting equity, so a run of sales often says nothing directional. Codes A and M are grants and option exercises rather than open-market decisions.
Full filing history and per-insider positions are on the UPWK quote page; the site-wide leaderboard is on the insider transactions hub.
Market data may be delayed, incomplete, or inaccurate. Not a recommendation to buy, sell, or hold any security. Verify quotes with your broker before trading. See Terms §17.