Upwork's three largest insider shareholders as of August 27, 2026 are Thomas Layton (Director, 3.97Mn shares), Thomas Layton (Director, 1.62Mn shares), Gregory C. Gretsch (Director, 1.00Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Gregory C. Gretsch | Director | 243,044 | 761,201 | 1,004,245 | 30.0% | 11 Jun, 2024 |
| 2 | Hayden Brown | President Ceo | 771,076 | 0 | 771,076 | 23.1% | 20 Aug, 2026 |
| 3 | Erica Gessert | Chief Financial Officer | 364,789 | 0 | 364,789 | 10.9% | 20 Aug, 2026 |
| 4 | Elizabeth A Nelson | Director | 0 | 356,712 | 356,712 | 10.7% | 14 May, 2025 |
| 5 | Kevin Harvey | Director | 147,216 | 0 | 147,216 | 4.4% | 08 Jun, 2026 |
| 6 | Jeff Mccombs | Chief Financial Officer | 97,264 | 0 | 97,264 | 2.9% | 22 Nov, 2022 |
| 7 | Gary Steele | Director | 85,129 | 0 | 85,129 | 2.5% | 25 Nov, 2025 |
| 8 | Anilu Vazquez-Ubarri | Director | 83,968 | 0 | 83,968 | 2.5% | 09 Jun, 2025 |
| 9 | Leela Srinivasan | Director | 79,469 | 0 | 79,469 | 2.4% | 09 Jun, 2025 |
| 10 | Glenn Kelman | Director | 66,422 | 0 | 66,422 | 2.0% | 08 Jun, 2026 |
| 11 | David H Lissy | Director | 66,026 | 0 | 66,026 | 2.0% | 08 Jun, 2026 |
| 12 | Dana L Evan | Director | 56,835 | 0 | 56,835 | 1.7% | 08 Jun, 2026 |
| 13 | Thomas Layton | Director | 52,296 | 0 | 52,296 | 1.6% | 08 Jun, 2026 |
| 14 | Eric Gilpin | Chief Sales Officer | 51,188 | 0 | 51,188 | 1.5% | 22 Feb, 2023 |
| 15 | Claire Bramley | Director | 45,146 | 0 | 45,146 | 1.4% | 08 Jun, 2026 |
| 16 | Anthony Ray Kappus | Gm Chief Operating Officer | 7,214 | 0 | 7,214 | 0.2% | 20 Aug, 2026 |
| 17 | Sabrina Mekhalfa | Chief Accounting Officer | 4,396 | 0 | 4,396 | 0.1% | 23 Jun, 2026 |
| 18 | Dave Bottoms | Gm, Marketplace | 2,678 | 0 | 2,678 | 0.1% | 20 Mar, 2026 |
| 19 | Olivier Marie | Chief Accounting Officer | 748 | 0 | 748 | 0.0% | 21 Aug, 2025 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 18 Aug, 2026 | Hayden Brown | President Ceo | Acquired M | 14,850 | — | — | 812,345 | Direct |
| 18 Aug, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Acquired M | 5,115 | — | — | 9,178 | Direct |
| 18 Aug, 2026 | Erica Gessert | Chief Financial Officer | Acquired M | 37,500 | — | — | 379,109 | Direct |
| 18 Aug, 2026 | Hayden Brown | President Ceo | Acquired M | 18,333 | — | — | 830,678 | Direct |
| 18 Aug, 2026 | Erica Gessert | Chief Financial Officer | Acquired M | 8,524 | — | — | 387,633 | Direct |
| 18 Aug, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Disposed S | 1,964 | $8.43 | $16.55K | 7,214 | Direct |
| 18 Aug, 2026 | Erica Gessert | Chief Financial Officer | Disposed S | 22,844 | $8.43 | $192.48K | 364,789 | Direct |
| 18 Aug, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Disposed M | 5,115 | $0.00 | $0 | 71,604 | Direct |
| 18 Aug, 2026 | Hayden Brown | President Ceo | Acquired M | 13,639 | — | — | 844,317 | Direct |
| 18 Aug, 2026 | Hayden Brown | President Ceo | Disposed S | 23,241 | $8.43 | $195.82K | 821,076 | Direct |
| 18 Aug, 2026 | Erica Gessert | Chief Financial Officer | Disposed M | 37,500 | $0.00 | $0 | 112,500 | Direct |
| 18 Aug, 2026 | Hayden Brown | President Ceo | Disposed S | 50,000 | $8.43 | $421.35K | 771,076 | Direct |
| 18 Aug, 2026 | Erica Gessert | Chief Financial Officer | Disposed M | 8,524 | $0.00 | $0 | 119,340 | Direct |
| 18 Aug, 2026 | Hayden Brown | President Ceo | Disposed M | 14,850 | $0.00 | $0 | 29,700 | Direct |
| 18 Aug, 2026 | Hayden Brown | President Ceo | Disposed M | 18,333 | $0.00 | $0 | 36,667 | Direct |
| 18 Aug, 2026 | Hayden Brown | President Ceo | Disposed M | 13,639 | $0.00 | $0 | 190,944 | Direct |
| 18 Jul, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Acquired M | 1,412 | — | — | 4,621 | Direct |
| 18 Jul, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Disposed S | 558 | $9.06 | $5.05K | 4,063 | Direct |
| 18 Jul, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Disposed M | 1,412 | $0.00 | $0 | 21,191 | Direct |
| 18 Jun, 2026 | Hayden Brown | President Ceo | Acquired M | 17,733 | — | — | 792,285 | Direct |