Erica Gessert, Chief Financial Officer of Upwork Inc. ($UPWK), sold about $1.8 million in company shares across nine open market transactions over the last year. Her most recent sale occurred on February 18, 2026. These sales rank her 3700th among 11,678 insiders by total value sold, compared to an average of $8.6 million per insider and roughly 6.4 transactions. Gessert made no open market purchases in this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| March 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8433 | $0.00 | 67,463.0000 | 140,660,000 | 11.11% | 0.01% |
| March 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 9278 | $12.31 | 307,240.0000 | 140,660,000 | 2.93% | 0.01% |
| March 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 9699 | $0.00 | 316,518.0000 | 140,660,000 | 3.16% | 0.01% |
| March 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8433 | $0.00 | 306,819.0000 | 140,660,000 | 2.83% | 0.01% |
| March 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 9699 | $0.00 | 116,397.0000 | 140,660,000 | 7.69% | 0.01% |
| Feb. 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 26292 | $13.80 | 298,386.0000 | 140,660,000 | 8.10% | 0.02% |
| Feb. 17, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Performance Stock Units | 40477 | $0.00 | 0.0000 | 140,660,000 | 100.00% | 0.03% |
| Feb. 17, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 40477 | $0.00 | 287,178.0000 | 140,660,000 | 16.41% | 0.03% |
| Feb. 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 37500 | $0.00 | 324,678.0000 | 140,660,000 | 13.06% | 0.03% |
| Feb. 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | A | Restricted Stock Units | 136388 | $0.00 | 136,388.0000 | 140,660,000 | 9999.99% | 0.10% |
| Feb. 18, 2026 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 37500 | $0.00 | 187,500.0000 | 140,660,000 | 16.67% | 0.03% |
| Dec. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 9700 | $0.00 | 126,096.0000 | 140,910,018 | 7.14% | 0.01% |
| Dec. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8433 | $0.00 | 75,896.0000 | 140,910,018 | 10.00% | 0.01% |
| Dec. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 9044 | $20.59 | 246,701.0000 | 140,910,018 | 3.54% | 0.01% |
| Dec. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 9700 | $0.00 | 255,745.0000 | 140,910,018 | 3.94% | 0.01% |
| Dec. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8433 | $0.00 | 246,045.0000 | 140,910,018 | 3.55% | 0.01% |
| Nov. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 9434 | $17.24 | 237,612.0000 | 140,910,018 | 3.82% | 0.01% |
| Nov. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 9059 | $16.14 | 247,046.0000 | 140,910,018 | 3.54% | 0.01% |
| Nov. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 37500 | $0.00 | 256,105.0000 | 140,910,018 | 17.15% | 0.03% |
| Nov. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 37500 | $0.00 | 225,000.0000 | 140,910,018 | 14.29% | 0.03% |
| Sept. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8433 | $0.00 | 84,329.0000 | 143,152,029 | 9.09% | 0.01% |
| Sept. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 9700 | $0.00 | 227,335.0000 | 143,152,029 | 4.46% | 0.01% |
| Sept. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8433 | $0.00 | 217,635.0000 | 143,152,029 | 4.03% | 0.01% |
| Sept. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 9700 | $0.00 | 135,796.0000 | 143,152,029 | 6.67% | 0.01% |
| Sept. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 8730 | $19.16 | 218,605.0000 | 143,152,029 | 3.84% | 0.01% |
| Aug. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 37500 | $0.00 | 262,500.0000 | 143,152,029 | 12.50% | 0.03% |
| Aug. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 19036 | $13.84 | 209,202.0000 | 143,152,029 | 8.34% | 0.01% |
| Aug. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 37500 | $0.00 | 228,238.0000 | 143,152,029 | 19.66% | 0.03% |
| June 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 9699 | $0.00 | 145,496.0000 | 143,152,029 | 6.25% | 0.01% |
| June 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8433 | $0.00 | 190,306.0000 | 143,152,029 | 4.64% | 0.01% |
| June 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 9699 | $0.00 | 200,005.0000 | 143,152,029 | 5.10% | 0.01% |
| June 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 9267 | $13.51 | 190,738.0000 | 143,152,029 | 4.63% | 0.01% |
| June 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8433 | $0.00 | 92,762.0000 | 143,152,029 | 8.33% | 0.01% |
| May 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 37500 | $0.00 | 300,000.0000 | 143,152,029 | 11.11% | 0.03% |
| May 19, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 19677 | $16.56 | 181,873.0000 | 143,152,029 | 9.76% | 0.01% |
| May 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 37500 | $0.00 | 201,550.0000 | 143,152,029 | 22.86% | 0.03% |
| March 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8433 | $0.00 | 101,195.0000 | 143,152,029 | 7.69% | 0.01% |
| March 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8433 | $0.00 | 165,261.0000 | 143,152,029 | 5.38% | 0.01% |
| March 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 4316 | $13.07 | 160,945.0000 | 143,152,029 | 2.61% | 0.00% |
| March 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | A | Restricted Stock Units | 155195 | $0.00 | 155,195.0000 | 143,152,029 | 9999.99% | 0.11% |
| Feb. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 37500 | $0.00 | 170,593.0000 | 143,152,029 | 28.18% | 0.03% |
| Feb. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 13765 | $16.15 | 156,828.0000 | 143,152,029 | 8.07% | 0.01% |
| Feb. 18, 2025 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 37500 | $0.00 | 337,500.0000 | 143,152,029 | 10.00% | 0.03% |
| Dec. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 4279 | $17.11 | 133,093.0000 | 140,552,454 | 3.11% | 0.00% |
| Dec. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8433 | $0.00 | 137,372.0000 | 140,552,454 | 6.54% | 0.01% |
| Dec. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8433 | $0.00 | 109,628.0000 | 140,552,454 | 7.14% | 0.01% |
| Nov. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 37500 | $0.00 | 148,755.0000 | 140,552,454 | 33.71% | 0.03% |
| Nov. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 37500 | $0.00 | 375,000.0000 | 140,552,454 | 9.09% | 0.03% |
| Nov. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 19816 | $15.13 | 128,939.0000 | 140,552,454 | 13.32% | 0.01% |
| Sept. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8433 | $0.00 | 115,746.0000 | 137,263,230 | 7.86% | 0.01% |
| Sept. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 4491 | $10.57 | 111,255.0000 | 137,263,230 | 3.88% | 0.00% |
| Sept. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8433 | $0.00 | 118,061.0000 | 137,263,230 | 6.67% | 0.01% |
| Aug. 19, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 20353 | $9.65 | 107,313.0000 | 137,263,230 | 15.94% | 0.01% |
| Aug. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 37500 | $0.00 | 412,500.0000 | 137,263,230 | 8.33% | 0.03% |
| Aug. 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 37500 | $0.00 | 127,666.0000 | 137,263,230 | 41.59% | 0.03% |
| June 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 8432 | $0.00 | 94,703.0000 | 137,263,230 | 9.77% | 0.01% |
| June 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 8432 | $0.00 | 126,494.0000 | 137,263,230 | 6.25% | 0.01% |
| June 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 4537 | $10.22 | 90,166.0000 | 137,263,230 | 4.79% | 0.00% |
| May 20, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | S | Common Stock | 69940 | $11.61 | 86,271.0000 | 137,263,230 | 44.77% | 0.05% |
| May 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Restricted Stock Units | 150000 | $0.00 | 450,000.0000 | 137,263,230 | 25.00% | 0.11% |
| May 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | M | Common Stock | 150000 | $0.00 | 156,211.0000 | 137,263,230 | 2415.07% | 0.11% |
| March 18, 2024 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | A | Restricted Stock Units | 134926 | $0.00 | 134,926.0000 | 137,263,230 | 9999.99% | 0.10% |
| May 18, 2023 | UPWORK, INC | $UPWK | Gessert Erica | Chief Financial Officer | A | Restricted Stock Units (RSU) | 600000 | $0.00 | 600,000.0000 | 130,518,000 | 9999.99% | 0.46% |