UPWK (Upwork Inc. Common Stock)
Insider Trading Activity
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.
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.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-08-20 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | — | — |
| 2026-08-20 | Hayden Brown | President & CEO | MIXED | — | — |
| 2026-08-20 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2026-07-21 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | — | — |
| 2026-06-23 | Hayden Brown | President & CEO | MIXED | — | — |
| 2026-06-23 | Sabrina Mekhalfa | Chief Accounting Officer | MIXED | — | — |
| 2026-06-23 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2026-06-08 | DANA L EVAN | Director | A | — | — |
| 2026-06-08 | KEVIN HARVEY | Director | A | — | — |
| 2026-06-08 | DAVID H LISSY | Director | A | — | — |
| 2026-06-08 | GLENN KELMAN | Director | A | — | — |
| 2026-06-08 | THOMAS LAYTON | Director | A | — | — |
| 2026-06-08 | CLAIRE BRAMLEY | Director | A | — | — |
| 2026-06-08 | Gary Steele | Director | A | — | — |
| 2026-05-20 | Anthony Ray Kappus | GM & Chief Operating Officer | MIXED | — | — |
| 2026-05-20 | Hayden Brown | President & CEO | MIXED | — | — |
| 2026-05-20 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2026-04-21 | Anthony Ray Kappus | GM & Chief Operating Officer | A | — | — |
| 2026-03-20 | Sabrina Mekhalfa | Chief Accounting Officer | MIXED | — | — |
| 2026-03-20 | Hayden Brown | President & CEO | MIXED | — | — |
| 2026-03-20 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2026-03-20 | Dave Bottoms | GM, Marketplace | MIXED | — | — |
| 2026-02-19 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2026-02-19 | Dave Bottoms | GM, Marketplace | MIXED | — | — |
| 2026-02-19 | Hayden Brown | President & CEO | MIXED | — | — |
| 2025-12-22 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2025-12-22 | Dave Bottoms | GM, Marketplace | MIXED | — | — |
| 2025-12-22 | Sabrina Mekhalfa | Chief Accounting Officer | A | — | — |
| 2025-12-22 | Hayden Brown | President & CEO | MIXED | — | — |
| 2025-11-28 | Hayden Brown | President & CEO | Sell | — | — |
| 2025-11-25 | Hayden Brown | President & CEO | Sell | — | — |
| 2025-11-25 | Gary Steele | Director | Sell | — | — |
| 2025-11-20 | Hayden Brown | President & CEO | MIXED | — | — |
| 2025-11-20 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2025-11-19 | Dave Bottoms | GM, Marketplace | MIXED | — | — |
| 2025-09-22 | Dave Bottoms | GM, Marketplace | MIXED | — | — |
| 2025-09-22 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2025-09-19 | Hayden Brown | President & CEO | MIXED | — | — |
| 2025-09-03 | Dave Bottoms | GM, Marketplace | Sell | — | — |
| 2025-08-21 | Olivier Marie | Chief Accounting Officer | Sell | — | — |
| 2025-08-20 | Dave Bottoms | GM, Marketplace | MIXED | — | — |
| 2025-08-20 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2025-08-19 | Hayden Brown | President & CEO | MIXED | — | — |
| 2025-08-18 | Olivier Marie | Chief Accounting Officer | MIXED | — | — |
| 2025-08-12 | Dave Bottoms | GM, Marketplace | Sell | — | — |
| 2025-06-24 | Olivier Marie | Chief Accounting Officer | Sell | — | — |
| 2025-06-23 | Hayden Brown | President & CEO | MIXED | — | — |
| 2025-06-23 | Erica Gessert | Chief Financial Officer | MIXED | — | — |
| 2025-06-23 | Dave Bottoms | GM, Marketplace | MIXED | — | — |
| 2025-06-23 | Olivier Marie | Chief Accounting Officer | MIXED | — | — |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| — | 10%+ Owner | 14,603,885 | — |
| — | 10%+ Owner | 14,603,885 | — |
| — | 10%+ Owner | 9,852,570 | — |
| — | 10%+ Owner | 9,852,570 | — |
| — | 10%+ Owner | 6,594,415 | — |
| — | Director | 1,898,531 | — |
| — | Director | 1,691,430 | — |
| — | Director | 959,839 | — |
| — | President & CEO | 830,678 | — |
| — | Chief Financial Officer | 387,633 | — |
| — | Director | 373,011 | — |
| — | President & CEO | 281,567 | — |
| — | 10%+ Owner | 244,770 | — |
| — | Director | 190,730 | — |
| — | 10%+ Owner | 183,090 | — |
| — | 10%+ Owner | 121,813 | — |
| — | Director | 112,216 | — |
| — | Chief Financial Officer | 103,459 | — |
| — | Director | 83,968 | — |
| — | Director | 82,783 | — |
| — | Director | 66,422 | — |
| — | Director | 66,026 | — |
| — | Director | 56,835 | — |
| — | Chief Sales Officer | 46,236 | — |
| — | Director | 45,146 | — |
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.