Upwork, Inc (UPWK) insider trading
Every open-market stock purchase and sale by Upwork, Inc executives, directors, large shareholders and members of Congress, from SEC Form 4 filings. Sector: Other.
Insider activity at a glance
- Hayden Brown (CEO) and 3 others sold $1.5M in the last 90 days.
- Last insider buy: Kevin Harvey (Director), $1M, 4 years ago.
Last 12 months: insiders bought $0 (0 buys) and sold $15.8M (31 sales). Last close $8.75 on Oct 21, 2026.
Recent UPWK insider trades
| Date | Insider | Trade | Value |
|---|---|---|---|
| Oct 19, 2026 | Anthony Ray Kappus (COO) | Sold | $4.7K |
| Oct 18, 2026 | Anthony Ray Kappus (COO) | Bought (not open market) | — |
| Oct 18, 2026 | Anthony Ray Kappus (COO) | Bought (not open market) | — |
| Sep 18, 2026 | Anthony Ray Kappus (COO) | Sold | $386K |
| Sep 18, 2026 | Hayden Brown (CEO) | Sold | $202K |
| Sep 18, 2026 | Erica Gessert (CFO) | Sold | $78.9K |
| Sep 18, 2026 | Sabrina Mekhalfa (C-suite exec) | Sold | $11K |
| Sep 18, 2026 | Anthony Ray Kappus (COO) | Bought (not open market) | — |
| Sep 18, 2026 | Hayden Brown (CEO) | Bought (not open market) | — |
| Sep 18, 2026 | Hayden Brown (CEO) | Bought (not open market) | — |
| Sep 18, 2026 | Erica Gessert (CFO) | Bought (not open market) | — |
| Sep 18, 2026 | Erica Gessert (CFO) | Bought (not open market) | — |
| Sep 18, 2026 | Sabrina Mekhalfa (C-suite exec) | Bought (not open market) | — |
| Aug 18, 2026 | Hayden Brown (CEO) | Sold | $421K |
| Aug 18, 2026 | Hayden Brown (CEO) | Sold | $196K |
| Aug 18, 2026 | Erica Gessert (CFO) | Sold | $192K |
| Aug 18, 2026 | Anthony Ray Kappus (COO) | Sold | $16.5K |
| Aug 18, 2026 | Hayden Brown (CEO) | Bought (not open market) | — |
| Aug 18, 2026 | Hayden Brown (CEO) | Bought (not open market) | — |
| Aug 18, 2026 | Hayden Brown (CEO) | Bought (not open market) | — |
| Aug 18, 2026 | Erica Gessert (CFO) | Bought (not open market) | — |
| Aug 18, 2026 | Erica Gessert (CFO) | Bought (not open market) | — |
| Aug 18, 2026 | Anthony Ray Kappus (COO) | Bought (not open market) | — |
| Jul 18, 2026 | Anthony Ray Kappus (COO) | Sold | $5.1K |
| Jul 18, 2026 | Anthony Ray Kappus (COO) | Bought (not open market) | — |
Who's trading UPWK
- Anthony Ray Kappus, COO: sold $429K (5 sales), last Oct 19, 2026
- Erica Gessert, CFO: sold $1.5M (9 sales), last Sep 18, 2026
- Hayden Brown, CEO: sold $12.4M (16 sales), last Sep 18, 2026
- Sabrina Mekhalfa, C-suite exec: sold $39.6K (3 sales), last Sep 18, 2026
- Claire Bramley, Insider: other filings, last Jun 4, 2026
- Dana L Evan, Insider: other filings, last Jun 4, 2026
- Kevin Harvey, Insider: other filings, last Jun 4, 2026
- Glenn Kelman, Insider: other filings, last Jun 4, 2026
- Thomas Layton, Insider: other filings, last Jun 4, 2026
- David H Lissy, Insider: other filings, last Jun 4, 2026
- Gary Steele, Insider: sold $219K (1 sale), last Jun 4, 2026
- Dave Bottoms, Insider: sold $1.2M (10 sales), last Mar 19, 2026
Get free alerts when an insider at Upwork, Inc files a new trade →