-$35M
Net insider buying / selling at Upwork (UPWK) over the last 2 years. Updated Jul 21, 2026
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Are Upwork Insiders Buying or Selling?
Upwork (UPWK) has had 8 insider transactions in the past 90 days, all sells. The most recent was Kappus Anthony Ray, who sold 558 shares at $9.06 on July 18, 2026.
Insider trading patterns can signal confidence or concern from the people who know the company best. AltIndex tracks insider transactions as one of 25+ alternative data signals in the UPWK AI Score. For government officials trading this stock, see UPWK congressional trading.
Who’s Trading Upwork Stock?
| Insider | Activity | Trades | Last Trade |
|---|---|---|---|
| Hayden Brown | Sold $20M | 36 | Jun 18, 2026 |
| ELIZABETH NELSON | Sold $4.5M | 5 | May 12, 2025 |
| THOMAS LAYTON | Sold $4.4M | 1 | May 14, 2025 |
| Erica Gessert | Sold $3M | 17 | Jun 18, 2026 |
| Dave Bottoms | Sold $2.9M | 33 | Mar 19, 2026 |
| Olivier Marie | Sold $600,000 | 25 | Aug 19, 2025 |
Recent Upwork Insider Transactions
| Insider | Transaction Date | Type | Shares | Price | Value |
|---|---|---|---|---|---|
| Kappus Anthony Ray | Jul 18, 2026 | Sell | 558 | $9.06 | $5,100 |
| Hayden Brown | Jun 18, 2026 | Sell | 23,468 | $8.15 | $190,000 |
| Erica Gessert | Jun 18, 2026 | Sell | 9,169 | $8.15 | $75,000 |
| Sabrina Mekhalfa | Jun 18, 2026 | Sell | 1,276 | $8.15 | $10,000 |
| Erica Gessert | May 18, 2026 | Sell | 22,162 | $8.66 | $190,000 |
| Hayden Brown | May 18, 2026 | Sell | 50,000 | $8.57 | $430,000 |
| Hayden Brown | May 18, 2026 | Sell | 22,546 | $8.66 | $200,000 |
| Kappus Anthony Ray | May 18, 2026 | Sell | 1,905 | $8.66 | $17,000 |
| Dave Bottoms | Mar 19, 2026 | Sell | 7,000 | $11.49 | $80,000 |
| Dave Bottoms | Mar 18, 2026 | Sell | 11,575 | $12.31 | $140,000 |
| Hayden Brown | Mar 18, 2026 | Sell | 23,745 | $12.31 | $290,000 |
| Erica Gessert | Mar 18, 2026 | Sell | 9,278 | $12.31 | $110,000 |
| Sabrina Mekhalfa | Mar 18, 2026 | Sell | 1,482 | $12.31 | $18,000 |
| Dave Bottoms | Feb 19, 2026 | Sell | 15,649 | $13.51 | $210,000 |
| Dave Bottoms | Feb 18, 2026 | Sell | 17,013 | $13.8 | $230,000 |
| Erica Gessert | Feb 18, 2026 | Sell | 26,292 | $13.8 | $360,000 |
| Hayden Brown | Feb 18, 2026 | Sell | 73,152 | $13.8 | $1M |
| Hayden Brown | Feb 18, 2026 | Sell | 50,000 | $13.79 | $690,000 |
| Dave Bottoms | Dec 19, 2025 | Sell | 9,622 | $20.66 | $200,000 |
| Dave Bottoms | Dec 18, 2025 | Sell | 11,285 | $20.59 | $230,000 |
| Hayden Brown | Dec 18, 2025 | Sell | 23,147 | $20.59 | $480,000 |
| Erica Gessert | Dec 18, 2025 | Sell | 9,044 | $20.59 | $190,000 |
| Hayden Brown | Nov 26, 2025 | Sell | 175,000 | $19.43 | $3.4M |
| Hayden Brown | Nov 26, 2025 | Sell | 100,000 | $19.44 | $1.9M |
| Hayden Brown | Nov 25, 2025 | Sell | 75,000 | $19.78 | $1.5M |
| Hayden Brown | Nov 21, 2025 | Sell | 60,000 | $18.2 | $1.1M |
| Gary Steele | Nov 21, 2025 | Sell | 12,500 | $17.51 | $220,000 |
| Dave Bottoms | Nov 19, 2025 | Sell | 1,748 | $18.13 | $32,000 |
| Hayden Brown | Nov 18, 2025 | Sell | 12,732 | $17.24 | $220,000 |
| Hayden Brown | Nov 18, 2025 | Sell | 12,114 | $16.14 | $200,000 |
| Dave Bottoms | Nov 18, 2025 | Sell | 1,047 | $17.24 | $18,000 |
| Erica Gessert | Nov 18, 2025 | Sell | 9,434 | $17.24 | $160,000 |
| Erica Gessert | Nov 18, 2025 | Sell | 9,059 | $16.14 | $150,000 |
| Dave Bottoms | Nov 18, 2025 | Sell | 955 | $16.14 | $15,000 |
| Dave Bottoms | Nov 17, 2025 | Sell | 561 | $16.45 | $9,200 |
| Dave Bottoms | Sep 19, 2025 | Sell | 10,014 | $19.96 | $200,000 |
| Hayden Brown | Sep 19, 2025 | Sell | 20,000 | $20 | $400,000 |
| Dave Bottoms | Sep 18, 2025 | Sell | 10,894 | $19.16 | $210,000 |
| Hayden Brown | Sep 18, 2025 | Sell | 22,344 | $19.16 | $430,000 |
| Erica Gessert | Sep 18, 2025 | Sell | 8,730 | $19.16 | $170,000 |
| Dave Bottoms | Aug 29, 2025 | Sell | 1,690 | $14.95 | $25,000 |
| Olivier Marie | Aug 19, 2025 | Sell | 1,686 | $13.88 | $23,000 |
| Erica Gessert | Aug 18, 2025 | Sell | 19,036 | $13.84 | $260,000 |
| Hayden Brown | Aug 18, 2025 | Sell | 25,577 | $13.84 | $350,000 |
| Dave Bottoms | Aug 18, 2025 | Sell | 2,060 | $13.84 | $29,000 |
| Olivier Marie | Aug 18, 2025 | Sell | 941 | $13.84 | $13,000 |
| Hayden Brown | Aug 15, 2025 | Sell | 60,000 | $13.76 | $830,000 |
| Olivier Marie | Aug 14, 2025 | Sell | 1,294 | $14 | $18,000 |
| Dave Bottoms | Aug 8, 2025 | Sell | 9,000 | $12.88 | $120,000 |
| Olivier Marie | Jun 23, 2025 | Sell | 1,842 | $13.24 | $24,000 |
| Olivier Marie | Jun 20, 2025 | Sell | 748 | $13.24 | $9,900 |
| Hayden Brown | Jun 18, 2025 | Sell | 23,716 | $13.51 | $320,000 |
| Dave Bottoms | Jun 18, 2025 | Sell | 11,562 | $13.51 | $160,000 |
| Olivier Marie | Jun 18, 2025 | Sell | 1,879 | $13.5 | $25,000 |
| Erica Gessert | Jun 18, 2025 | Sell | 9,267 | $13.51 | $130,000 |
| Leela Srinivasan | Jun 6, 2025 | Sell | 3,314 | $15.36 | $51,000 |
| Leela Srinivasan | Jun 5, 2025 | Sell | 6,520 | $15.16 | $99,000 |
| Dave Bottoms | May 20, 2025 | Sell | 1,620 | $16.41 | $27,000 |
| Olivier Marie | May 20, 2025 | Sell | 1,655 | $16.41 | $27,000 |
| Erica Gessert | May 19, 2025 | Sell | 19,677 | $16.56 | $330,000 |
| Dave Bottoms | May 19, 2025 | Sell | 2,130 | $16.66 | $35,000 |
| Hayden Brown | May 19, 2025 | Sell | 9,620 | $16.56 | $160,000 |
| Hayden Brown | May 19, 2025 | Sell | 7,792 | $16.58 | $130,000 |
| Hayden Brown | May 19, 2025 | Sell | 5,032 | $16.61 | $84,000 |
| Hayden Brown | May 19, 2025 | Sell | 3,994 | $16.59 | $66,000 |
| Olivier Marie | May 19, 2025 | Sell | 528 | $16.78 | $8,900 |
| Olivier Marie | May 19, 2025 | Sell | 444 | $16.81 | $7,500 |
| Hayden Brown | May 15, 2025 | Sell | 60,000 | $17.16 | $1M |
| Olivier Marie | May 15, 2025 | Sell | 3,105 | $17.14 | $53,000 |
| Dave Bottoms | May 15, 2025 | Sell | 1,009 | $17.14 | $17,000 |
| THOMAS LAYTON | May 14, 2025 | Sell | 250,000 | $17.52 | $4.4M |
| Hayden Brown | May 12, 2025 | Sell | 20,000 | $17.09 | $340,000 |
| ELIZABETH NELSON | May 12, 2025 | Sell | 60,000 | $17.43 | $1M |
| Hayden Brown | May 7, 2025 | Sell | 40,000 | $15.92 | $640,000 |
| Dave Bottoms | Mar 19, 2025 | Sell | 9,593 | $13.46 | $130,000 |
| Olivier Marie | Mar 19, 2025 | Sell | 2,587 | $13.46 | $35,000 |
| Dave Bottoms | Mar 18, 2025 | Sell | 5,411 | $13.07 | $71,000 |
| Olivier Marie | Mar 18, 2025 | Sell | 1,460 | $13.07 | $19,000 |
| Erica Gessert | Mar 18, 2025 | Sell | 4,316 | $13.07 | $56,000 |
| Hayden Brown | Mar 18, 2025 | Sell | 9,075 | $13.07 | $120,000 |
| Hayden Brown | Mar 7, 2025 | Sell | 60,000 | $14.2 | $850,000 |
| ELIZABETH NELSON | Feb 19, 2025 | Sell | 73,101 | $17.57 | $1.3M |
| ELIZABETH NELSON | Feb 19, 2025 | Sell | 1,899 | $18.01 | $34,000 |
| Dave Bottoms | Feb 19, 2025 | Sell | 2,207 | $17.69 | $39,000 |
| Olivier Marie | Feb 19, 2025 | Sell | 1,546 | $17.71 | $27,000 |
| Erica Gessert | Feb 18, 2025 | Sell | 13,765 | $16.15 | $220,000 |
| Hayden Brown | Feb 18, 2025 | Sell | 21,122 | $16.15 | $340,000 |
| Dave Bottoms | Feb 18, 2025 | Sell | 1,543 | $16.15 | $25,000 |
| Olivier Marie | Feb 18, 2025 | Sell | 1,081 | $16.15 | $17,000 |
| Olivier Marie | Feb 14, 2025 | Sell | 335 | $16.48 | $5,500 |
| Olivier Marie | Jan 21, 2025 | Sell | 257 | $16 | $4,100 |
| Olivier Marie | Dec 19, 2024 | Sell | 2,601 | $16.23 | $42,000 |
| Dave Bottoms | Dec 19, 2024 | Sell | 9,642 | $16.23 | $160,000 |
| ELIZABETH NELSON | Dec 18, 2024 | Sell | 75,000 | $17.37 | $1.3M |
| Olivier Marie | Dec 18, 2024 | Sell | 1,448 | $17.11 | $25,000 |
| Erica Gessert | Dec 18, 2024 | Sell | 4,279 | $17.11 | $73,000 |
| Dave Bottoms | Dec 18, 2024 | Sell | 5,360 | $17.11 | $92,000 |
| Hayden Brown | Dec 18, 2024 | Sell | 8,997 | $17.12 | $150,000 |
| Hayden Brown | Dec 16, 2024 | Sell | 20,000 | $16.84 | $340,000 |
| Hayden Brown | Nov 27, 2024 | Sell | 15,000 | $17 | $260,000 |
| Olivier Marie | Nov 19, 2024 | Sell | 1,649 | $14.9 | $25,000 |
| Dave Bottoms | Nov 19, 2024 | Sell | 2,354 | $14.9 | $35,000 |
| Erica Gessert | Nov 18, 2024 | Sell | 19,816 | $15.13 | $300,000 |
| Hayden Brown | Nov 18, 2024 | Sell | 30,672 | $15.13 | $460,000 |
| Dave Bottoms | Nov 18, 2024 | Sell | 1,396 | $15.13 | $21,000 |
| Olivier Marie | Nov 18, 2024 | Sell | 978 | $15.13 | $15,000 |
| Dave Bottoms | Nov 15, 2024 | Sell | 983 | $14.94 | $15,000 |
| Dave Bottoms | Nov 8, 2024 | Sell | 10,508 | $15.86 | $170,000 |
| Hayden Brown | Nov 8, 2024 | Sell | 10,000 | $15.85 | $160,000 |
| Olivier Marie | Nov 8, 2024 | Sell | 9,153 | $15.92 | $150,000 |
| Olivier Marie | Oct 18, 2024 | Sell | 223 | $10.3 | $2,300 |
| Dave Bottoms | Sep 19, 2024 | Sell | 4,688 | $10.74 | $50,000 |
| ELIZABETH NELSON | Sep 18, 2024 | Sell | 75,000 | $10.54 | $790,000 |
| Dave Bottoms | Sep 18, 2024 | Sell | 5,626 | $10.57 | $59,000 |
| Erica Gessert | Sep 18, 2024 | Sell | 4,491 | $10.57 | $47,000 |
| Hayden Brown | Sep 18, 2024 | Sell | 9,444 | $10.57 | $100,000 |
| Hayden Brown | Sep 16, 2024 | Sell | 20,000 | $10.01 | $200,000 |
| Dave Bottoms | Aug 27, 2024 | Sell | 5,818 | $9.81 | $57,000 |
| Olivier Marie | Aug 20, 2024 | Sell | 1,622 | $9.44 | $15,000 |
| Hayden Brown | Aug 19, 2024 | Sell | 31,506 | $9.65 | $300,000 |
| Erica Gessert | Aug 19, 2024 | Sell | 20,353 | $9.65 | $200,000 |
| Olivier Marie | Aug 19, 2024 | Sell | 1,005 | $9.65 | $9,700 |
| Dave Bottoms | Aug 19, 2024 | Sell | 1,433 | $9.65 | $14,000 |
| Olivier Marie | Aug 12, 2024 | Sell | 366 | $9.23 | $3,400 |
Frequently Asked Questions: Upwork Insider Trading
In the past 90 days, Upwork insiders have made 0 buys and 8 sells. The net selling may indicate insiders are taking profits or reducing exposure.
The most recent sale was by Kappus Anthony Ray who sold 558 shares on July 18, 2026. View all transactions in the table on this page.
Insider buying is generally a stronger signal than insider selling, since insiders may sell for personal reasons (diversification, taxes) but typically buy only when they believe the stock is undervalued. AltIndex uses insider transaction patterns alongside 25+ other signals in the AI Score.
Brown Hayden has sold the most UPWK stock in the last 2 years, with a total value of $20M.
The total value of insider transactions for Upwork in the last 2 years is negative, amounting to -$35M. This suggests that insiders have predominantly sold shares, which could reflect various personal or financial considerations rather than a straightforward outlook on the company's future performance.
The analytics provided are estimates and not a substitute for professional advice. All investments involve risks, including possible capital loss.
