16 insiders reported 202 Form 4 transactions for UPWORK, INC (UPWK) over the past 18 months (most recent 2026-08-20). Recent activity: Brown Hayden (President & CEO) Buy 14,850 shares, Kappus Anthony Ray (GM & Chief Operating Officer) Buy 5,115 shares, Gessert Erica (Chief Financial Officer) Buy 37,500 shares, Brown Hayden (President & CEO) Buy 18,333 shares, Kappus Anthony Ray (GM & Chief Operating Officer) Sell 1,964 shares. Source: SEC Form 4.
| Date | Insider | Title | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-08-20 | Brown Hayden | President & CEO | Buy | 14,850 | $0 |
| 2026-08-20 | Kappus Anthony Ray | GM & Chief Operating Officer | Buy | 5,115 | $0 |
| 2026-08-20 | Gessert Erica | Chief Financial Officer | Buy | 37,500 | $0 |
| 2026-08-20 | Brown Hayden | President & CEO | Buy | 18,333 | $0 |
| 2026-08-20 | Kappus Anthony Ray | GM & Chief Operating Officer | Sell | 1,964 | $16,548 |
| 2026-08-20 | Gessert Erica | Chief Financial Officer | Buy | 8,524 | $0 |
| 2026-08-20 | Brown Hayden | President & CEO | Buy | 13,639 | $0 |
| 2026-08-20 | Gessert Erica | Chief Financial Officer | Sell | 22,844 | $192,477 |
| 2026-08-20 | Brown Hayden | President & CEO | Sell | 23,241 | $195,822 |
| 2026-08-20 | Brown Hayden | President & CEO | Sell | 50,000 | $421,355 |
| 2026-07-21 | Kappus Anthony Ray | GM & Chief Operating Officer | Buy | 1,412 | $0 |
| 2026-07-21 | Kappus Anthony Ray | GM & Chief Operating Officer | Sell | 558 | $5,053 |
| 2026-06-23 | Brown Hayden | President & CEO | Buy | 17,733 | $0 |
| 2026-06-23 | Mekhalfa Sabrina | Chief Accounting Officer | Buy | 3,577 | $0 |
| 2026-06-23 | Gessert Erica | Chief Financial Officer | Buy | 8,432 | $0 |
| 2026-06-23 | Brown Hayden | President & CEO | Buy | 28,678 | $0 |
| 2026-06-23 | Mekhalfa Sabrina | Chief Accounting Officer | Sell | 1,276 | $10,401 |
| 2026-06-23 | Gessert Erica | Chief Financial Officer | Buy | 9,700 | $0 |
| 2026-06-23 | Gessert Erica | Chief Financial Officer | Sell | 9,169 | $74,734 |
| 2026-06-23 | Brown Hayden | President & CEO | Sell | 23,468 | $191,281 |
| 2026-06-08 | EVAN DANA L | Director | Buy | 20,880 | $0 |
| 2026-06-08 | HARVEY KEVIN | Director | Buy | 6,207 | $0 |
| 2026-06-08 | LISSY DAVID H | Director | Buy | 45,146 | $0 |
| 2026-06-08 | KELMAN GLENN | Director | Buy | 6,207 | $0 |
| 2026-06-08 | LAYTON THOMAS | Director | Buy | 6,207 | $0 |
Source: SEC Form 4 filings · as of 2026-08-20