UPWK's three largest insider shareholders as of September 29, 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 | 28.9% | 11 Jun, 2024 |
| 2 | Hayden Brown | President Ceo | 793,593 | 0 | 793,593 | 22.9% | 22 Sep, 2026 |
| 3 | Erica Gessert | Chief Financial Officer | 373,586 | 0 | 373,586 | 10.8% | 22 Sep, 2026 |
| 4 | Elizabeth A Nelson | Director | 0 | 356,712 | 356,712 | 10.3% | 14 May, 2025 |
| 5 | Kevin Harvey | Director | 147,216 | 0 | 147,216 | 4.2% | 08 Jun, 2026 |
| 6 | Gary Steele | Director | 112,216 | 0 | 112,216 | 3.2% | 08 Jun, 2026 |
| 7 | Jeff Mccombs | Chief Financial Officer | 97,264 | 0 | 97,264 | 2.8% | 22 Nov, 2022 |
| 8 | Anilu Vazquez-Ubarri | Director | 83,968 | 0 | 83,968 | 2.4% | 09 Jun, 2025 |
| 9 | Leela Srinivasan | Director | 79,469 | 0 | 79,469 | 2.3% | 09 Jun, 2025 |
| 10 | Anthony Ray Kappus | Gm Chief Operating Officer | 76,342 | 0 | 76,342 | 2.2% | 22 Sep, 2026 |
| 11 | Glenn Kelman | Director | 66,422 | 0 | 66,422 | 1.9% | 08 Jun, 2026 |
| 12 | David H Lissy | Director | 66,026 | 0 | 66,026 | 1.9% | 08 Jun, 2026 |
| 13 | Dana L Evan | Director | 56,835 | 0 | 56,835 | 1.6% | 08 Jun, 2026 |
| 14 | Thomas Layton | Director | 52,296 | 0 | 52,296 | 1.5% | 08 Jun, 2026 |
| 15 | Eric Gilpin | Chief Sales Officer | 51,188 | 0 | 51,188 | 1.5% | 22 Feb, 2023 |
| 16 | Claire Bramley | Director | 45,146 | 0 | 45,146 | 1.3% | 08 Jun, 2026 |
| 17 | Sabrina Mekhalfa | Chief Accounting Officer | 6,675 | 0 | 6,675 | 0.2% | 22 Sep, 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 Sep, 2026 | Hayden Brown | President Ceo | Acquired M | 17,733 | — | — | 788,809 | Direct |
| 18 Sep, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Acquired M | 114,860 | — | — | 122,074 | Direct |
| 18 Sep, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Acquired M | 3,578 | — | — | 7,974 | Direct |
| 18 Sep, 2026 | Erica Gessert | Chief Financial Officer | Acquired M | 8,433 | — | — | 373,222 | Direct |
| 18 Sep, 2026 | Hayden Brown | President Ceo | Acquired M | 28,677 | — | — | 817,486 | Direct |
| 18 Sep, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Disposed S | 1,299 | $8.45 | $10.98K | 6,675 | Direct |
| 18 Sep, 2026 | Erica Gessert | Chief Financial Officer | Acquired M | 9,700 | — | — | 382,922 | Direct |
| 18 Sep, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Disposed S | 45,732 | $8.45 | $386.47K | 76,342 | Direct |
| 18 Sep, 2026 | Anthony Ray Kappus | Gm Chief Operating Officer | Disposed M | 114,860 | $0.00 | $0 | 344,582 | Direct |
| 18 Sep, 2026 | Erica Gessert | Chief Financial Officer | Disposed S | 9,336 | $8.45 | $78.90K | 373,586 | Direct |
| 18 Sep, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Disposed M | 3,578 | $0.00 | $0 | 32,197 | Direct |
| 18 Sep, 2026 | Hayden Brown | President Ceo | Disposed S | 23,893 | $8.45 | $201.92K | 793,593 | Direct |
| 18 Sep, 2026 | Hayden Brown | President Ceo | Disposed M | 17,733 | $0.00 | $0 | 106,400 | Direct |
| 18 Sep, 2026 | Erica Gessert | Chief Financial Officer | Disposed M | 8,433 | $0.00 | $0 | 50,598 | Direct |
| 18 Sep, 2026 | Hayden Brown | President Ceo | Disposed M | 28,677 | $0.00 | $0 | 286,775 | Direct |
| 18 Sep, 2026 | Erica Gessert | Chief Financial Officer | Disposed M | 9,700 | $0.00 | $0 | 96,997 | 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 | 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 | 8,524 | — | — | 387,633 | Direct |