UPWORK INC (UPWK) — insider trading
Industrials · NASDAQ
UPWORK INC (UPWK) has 78 reported SEC Form 4 insider transactions in our data, including 16 open-market sales among the most recent 78 (latest 2026-09-18).
Recent Form 4 transactions
| Date | Insider | Role | Type | Shares | Price | Value | Filing |
|---|---|---|---|---|---|---|---|
| 2026-09-18 | Mekhalfa Sabrina | Officer (Chief Accounting Officer) | Option exercise / conversion (derivative) | 3,578 | — | $0 | Form 4 |
| 2026-09-18 | Mekhalfa Sabrina | Officer (Chief Accounting Officer) | Open-market sale | 1,299 | $8.45 | $11.0K | Form 4 |
| 2026-09-18 | Mekhalfa Sabrina | Officer (Chief Accounting Officer) | Option exercise / conversion | 3,578 | — | — | Form 4 |
| 2026-09-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion (derivative) | 114,860 | — | $0 | Form 4 |
| 2026-09-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Open-market sale | 45,732 | $8.45 | $386.5K | Form 4 |
| 2026-09-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion | 114,860 | — | — | Form 4 |
| 2026-09-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 9,700 | — | $0 | Form 4 |
| 2026-09-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 8,433 | — | $0 | Form 4 |
| 2026-09-18 | Gessert Erica | Officer (Chief Financial Officer) | Open-market sale | 9,336 | $8.45 | $78.9K | Form 4 |
| 2026-09-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 9,700 | — | — | Form 4 |
| 2026-09-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 8,433 | — | — | Form 4 |
| 2026-09-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 28,677 | — | $0 | Form 4 |
| 2026-09-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 17,733 | — | $0 | Form 4 |
| 2026-09-18 | Brown Hayden | Director, Officer (President & CEO) | Open-market sale | 23,893 | $8.45 | $201.9K | Form 4 |
| 2026-09-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 28,677 | — | — | Form 4 |
| 2026-09-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 17,733 | — | — | Form 4 |
| 2026-08-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion (derivative) | 5,115 | — | $0 | Form 4 |
| 2026-08-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Open-market sale | 1,964 | $8.43 | $16.5K | Form 4 |
| 2026-08-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion | 5,115 | — | — | Form 4 |
| 2026-08-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 8,524 | — | $0 | Form 4 |
| 2026-08-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 37,500 | — | $0 | Form 4 |
| 2026-08-18 | Gessert Erica | Officer (Chief Financial Officer) | Open-market sale | 22,844 | $8.43 | $192.5K | Form 4 |
| 2026-08-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 8,524 | — | — | Form 4 |
| 2026-08-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 37,500 | — | — | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 13,639 | — | $0 | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 18,333 | — | $0 | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 14,850 | — | $0 | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Open-market sale | 50,000 | $8.43 | $421.4K | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Open-market sale | 23,241 | $8.43 | $195.8K | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 13,639 | — | — | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 18,333 | — | — | Form 4 |
| 2026-08-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 14,850 | — | — | Form 4 |
| 2026-07-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion (derivative) | 1,412 | — | $0 | Form 4 |
| 2026-07-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Open-market sale | 558 | $9.06 | $5.1K | Form 4 |
| 2026-07-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion | 1,412 | — | — | Form 4 |
| 2026-06-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 28,678 | — | $0 | Form 4 |
| 2026-06-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 17,733 | — | $0 | Form 4 |
| 2026-06-18 | Brown Hayden | Director, Officer (President & CEO) | Open-market sale | 23,468 | $8.15 | $191.3K | Form 4 |
| 2026-06-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 28,678 | — | — | Form 4 |
| 2026-06-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 17,733 | — | — | Form 4 |
| 2026-06-18 | Mekhalfa Sabrina | Officer (Chief Accounting Officer) | Option exercise / conversion (derivative) | 3,577 | — | $0 | Form 4 |
| 2026-06-18 | Mekhalfa Sabrina | Officer (Chief Accounting Officer) | Open-market sale | 1,276 | $8.15 | $10.4K | Form 4 |
| 2026-06-18 | Mekhalfa Sabrina | Officer (Chief Accounting Officer) | Option exercise / conversion | 3,577 | — | — | Form 4 |
| 2026-06-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 9,700 | — | $0 | Form 4 |
| 2026-06-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 8,432 | — | $0 | Form 4 |
| 2026-06-18 | Gessert Erica | Officer (Chief Financial Officer) | Open-market sale | 9,169 | $8.15 | $74.7K | Form 4 |
| 2026-06-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 9,700 | — | — | Form 4 |
| 2026-06-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 8,432 | — | — | Form 4 |
| 2026-06-04 | HARVEY KEVIN | Director | Grant / award / vesting | 20,880 | — | $0 | Form 4 |
| 2026-06-04 | HARVEY KEVIN | Director | Grant / award / vesting | 6,207 | — | $0 | Form 4 |
| 2026-06-04 | EVAN DANA L | Director | Grant / award / vesting | 20,880 | — | $0 | Form 4 |
| 2026-06-04 | Steele Gary | Director | Grant / award / vesting | 20,880 | — | $0 | Form 4 |
| 2026-06-04 | Steele Gary | Director | Grant / award / vesting | 6,207 | — | $0 | Form 4 |
| 2026-06-04 | KELMAN GLENN | Director | Grant / award / vesting | 20,880 | — | $0 | Form 4 |
| 2026-06-04 | KELMAN GLENN | Director | Grant / award / vesting | 6,207 | — | $0 | Form 4 |
| 2026-06-04 | LAYTON THOMAS | Director | Grant / award / vesting | 20,880 | — | $0 | Form 4 |
| 2026-06-04 | LAYTON THOMAS | Director | Grant / award / vesting | 6,772 | — | $0 | Form 4 |
| 2026-06-04 | LAYTON THOMAS | Director | Grant / award / vesting | 6,207 | — | $0 | Form 4 |
| 2026-06-04 | LISSY DAVID H | Director | Grant / award / vesting | 20,880 | — | $0 | Form 4 |
| 2026-06-04 | LISSY DAVID H | Director | Grant / award / vesting | 45,146 | — | $0 | Form 4 |
| 2026-06-04 | BRAMLEY CLAIRE | Director | Grant / award / vesting | 45,146 | — | $0 | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 13,638 | — | $0 | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 18,334 | — | $0 | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion (derivative) | 14,850 | — | $0 | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Open-market sale | 50,000 | $8.57 | $428.5K | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Open-market sale | 22,546 | $8.66 | $195.3K | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 13,638 | — | — | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 18,334 | — | — | Form 4 |
| 2026-05-18 | Brown Hayden | Director, Officer (President & CEO) | Option exercise / conversion | 14,850 | — | — | Form 4 |
| 2026-05-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 8,524 | — | $0 | Form 4 |
| 2026-05-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion (derivative) | 37,500 | — | $0 | Form 4 |
| 2026-05-18 | Gessert Erica | Officer (Chief Financial Officer) | Open-market sale | 22,162 | $8.66 | $192.0K | Form 4 |
| 2026-05-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 8,524 | — | — | Form 4 |
| 2026-05-18 | Gessert Erica | Officer (Chief Financial Officer) | Option exercise / conversion | 37,500 | — | — | Form 4 |
| 2026-05-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion (derivative) | 5,114 | — | $0 | Form 4 |
| 2026-05-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Open-market sale | 1,905 | $8.66 | $16.5K | Form 4 |
| 2026-05-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Option exercise / conversion | 5,114 | — | — | Form 4 |
| 2026-04-18 | Kappus Anthony Ray | Officer (GM & Chief Operating Officer) | Grant / award / vesting (derivative) | 22,603 | — | $0 | Form 4 |
Ask the chat about UPWK's insider activity →
Transaction types are the SEC Form 4 codes: open-market purchases (P) and sales (S) are the only rows that reflect open-market conviction. Awards/vesting (A), option exercises (M/X/C), shares withheld for taxes (F) and gifts (G) are compensation or mechanical, not buying or selling on the open market. Sales may be planned and non-discretionary (e.g. a Rule 10b5-1 plan); open-market buying is not a recommendation to buy. Informational only — not financial advice.
Source: SEC EDGAR Form 3/4/5. See the full company profile: UPWORK INC (UPWK).
Last updated 2026-09-18 (most recent filing date).
Informational only — NOT financial advice. Insider filings are sourced from SEC EDGAR and shown with their reported dates.