Insider trading activities (stock purchases, sales, and option exercises) reported by insiders of Upwork, Inc (UPWK) since 2018 are shown in Table 1 and Table 2. Table 1 shows the monthly insider trading data of Upwork, Inc. Table 2 shows the detailed insider transactions. This company's CIK number is 1627475.
Total stock buying since 2018: $16,759,854.
Total stock sales since 2018: $140,103,730.
Total stock option exercises since 2018: $8,231,216.
| Insider Buying | Insider Sales | Option Exercises | ||||
|---|---|---|---|---|---|---|
| Year | Shares | Value | Shares | Value | Shares | Value |
| 2025 | 0 | $0 | 1,126,036 | $18,515,127 | 501,921 | $275,250 |
| 2024 | 0 | $0 | 709,291 | $9,115,134 | 952,335 | $1,058,372 |
| 2023 | 0 | $0 | 263,813 | $3,205,477 | 454,525 | $0 |
| 2022 | 65,828 | $1,074,247 | 294,220 | $4,737,328 | 563,633 | $0 |
| 2021 | 0 | $0 | 793,936 | $36,839,594 | 889,085 | $2,027,856 |
| 2020 | 1,365,840 | $15,685,607 | 359,037 | $7,630,881 | 475,816 | $633,600 |
| 2019 | 0 | $0 | 3,496,287 | $59,303,458 | 1,387,469 | $4,189,055 |
| 2018 | 0 | $0 | 54,246 | $756,731 | 14,246 | $47,083 |
| Trading Period | Insider Buying | Insider Sales | Option Exercises | |||
|---|---|---|---|---|---|---|
| year-month | Shares | Value | Shares | Value | Shares | Value |
| 2025-08 | 0 | $0 | 121,284 | $1,666,948 | 94,260 | $0 |
| 2025-06 | 0 | $0 | 58,848 | $811,000 | 90,666 | $0 |
| 2025-05 | 0 | $0 | 736,606 | $12,740,534 | 94,260 | $0 |
| 2025-03 | 0 | $0 | 92,442 | $1,280,682 | 45,217 | $0 |
| 2025-02 | 0 | $0 | 116,599 | $2,011,851 | 176,926 | $275,250 |
| 2025-01 | 0 | $0 | 257 | $4,112 | 592 | $0 |
| 2024-12 | 0 | $0 | 127,327 | $2,182,032 | 188,416 | $526,222 |
| 2024-11 | 0 | $0 | 102,509 | $1,599,943 | 101,920 | $0 |
| 2024-10 | 0 | $0 | 223 | $2,297 | 591 | $0 |
| 2024-09 | 0 | $0 | 123,296 | $1,290,903 | 120,217 | $275,250 |
| 2024-08 | 0 | $0 | 62,103 | $599,608 | 101,923 | $0 |
| 2024-07 | 0 | $0 | 225 | $2,565 | 591 | $0 |
| 2024-06 | 0 | $0 | 41,297 | $422,210 | 45,217 | $0 |
| 2024-05 | 0 | $0 | 184,521 | $2,160,108 | 284,419 | $256,900 |
| 2024-04 | 0 | $0 | 223 | $2,497 | 592 | $0 |
| 2024-03 | 0 | $0 | 20,967 | $253,218 | 2,635 | $0 |
| 2024-02 | 0 | $0 | 46,341 | $596,062 | 105,223 | $0 |
| 2024-01 | 0 | $0 | 259 | $3,691 | 591 | $0 |
| 2023-12 | 0 | $0 | 43,965 | $655,307 | 57,030 | $0 |
| 2023-11 | 0 | $0 | 28,932 | $414,539 | 45,820 | $0 |
| 2023-10 | 0 | $0 | 216 | $2,423 | 591 | $0 |
| 2023-09 | 0 | $0 | 29,419 | $374,385 | 57,030 | $0 |
| 2023-08 | 0 | $0 | 39,373 | $558,102 | 47,283 | $0 |
| 2023-07 | 0 | $0 | 222 | $2,364 | 592 | $0 |
| Trade Date | Insider Name | Trade Type | Shares | Price ($) | Value ($) |
|---|---|---|---|---|---|
| 2025-08-29 | Bottoms Dave (GM, Marketplace) | Sale | 1,690 | 14.95 | 25,265 |
| 2025-08-19 | Marie Olivier (Chief Accounting Officer) | Sale | 1,686 | 13.88 | 23,405 |
| 2025-08-18 | Bottoms Dave (GM, Marketplace) | Sale | 2,060 | 13.84 | 28,504 |
| 2025-08-18 | Bottoms Dave (GM, Marketplace) | Option Ex | 3,750 | .00 | 0 |
| 2025-08-18 | Gessert Erica (Chief Financial Officer) | Sale | 19,036 | 13.84 | 263,363 |
| 2025-08-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 37,500 | .00 | 0 |
| 2025-08-18 | Marie Olivier (Chief Accounting Officer) | Sale | 941 | 13.84 | 13,020 |
| 2025-08-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 2,627 | .00 | 0 |
| 2025-08-18 | Brown Hayden (President & CEO) | Sale | 25,577 | 13.84 | 353,857 |
| 2025-08-18 | Brown Hayden (President & CEO) | Option Ex | 50,383 | .00 | 0 |
| 2025-08-15 | Brown Hayden (President & CEO) | Sale | 60,000 | 13.76 | 825,480 |
| 2025-08-14 | Marie Olivier (Chief Accounting Officer) | Sale | 1,294 | 14.00 | 18,116 |
| 2025-08-08 | Bottoms Dave (GM, Marketplace) | Sale | 9,000 | 12.88 | 115,938 |
| 2025-06-23 | Marie Olivier (Chief Accounting Officer) | Sale | 1,842 | 13.24 | 24,391 |
| 2025-06-20 | Marie Olivier (Chief Accounting Officer) | Sale | 748 | 13.24 | 9,905 |
| 2025-06-18 | Bottoms Dave (GM, Marketplace) | Sale | 11,562 | 13.51 | 156,144 |
| 2025-06-18 | Bottoms Dave (GM, Marketplace) | Option Ex | 20,907 | .00 | 0 |
| 2025-06-18 | Gessert Erica (Chief Financial Officer) | Sale | 9,267 | 13.51 | 125,150 |
| 2025-06-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 18,132 | .00 | 0 |
| 2025-06-18 | Marie Olivier (Chief Accounting Officer) | Sale | 1,879 | 13.51 | 25,375 |
| 2025-06-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 5,217 | .00 | 0 |
| 2025-06-18 | Brown Hayden (President & CEO) | Sale | 23,716 | 13.51 | 320,284 |
| 2025-06-18 | Brown Hayden (President & CEO) | Option Ex | 46,410 | .00 | 0 |
| 2025-06-06 | Srinivasan Leela | Sale | 3,314 | 15.36 | 50,889 |
| 2025-06-05 | Srinivasan Leela | Sale | 6,520 | 15.16 | 98,862 |
| 2025-05-20 | Bottoms Dave (GM, Marketplace) | Sale | 1,620 | 16.41 | 26,584 |
| 2025-05-20 | Marie Olivier (Chief Accounting Officer) | Sale | 1,655 | 16.41 | 27,151 |
| 2025-05-19 | Bottoms Dave (GM, Marketplace) | Sale | 2,130 | 16.66 | 35,475 |
| 2025-05-19 | Gessert Erica (Chief Financial Officer) | Sale | 19,677 | 16.56 | 325,910 |
| 2025-05-19 | Marie Olivier (Chief Accounting Officer) | Sale | 972 | 16.79 | 16,321 |
| 2025-05-19 | Brown Hayden (President & CEO) | Sale | 26,438 | 16.59 | 438,527 |
| 2025-05-18 | Bottoms Dave (GM, Marketplace) | Option Ex | 3,750 | .00 | 0 |
| 2025-05-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 37,500 | .00 | 0 |
| 2025-05-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 2,627 | .00 | 0 |
| 2025-05-18 | Brown Hayden (President & CEO) | Option Ex | 50,383 | .00 | 0 |
| 2025-05-15 | Bottoms Dave (GM, Marketplace) | Sale | 1,009 | 17.14 | 17,295 |
| 2025-05-15 | Marie Olivier (Chief Accounting Officer) | Sale | 3,105 | 17.14 | 53,222 |
| 2025-05-15 | Brown Hayden (President & CEO) | Sale | 60,000 | 17.16 | 1,029,480 |
| 2025-05-14 | Layton Thomas | Sale | 250,000 | 17.52 | 4,379,750 |
| 2025-05-13 | Layton Thomas | Sale | 250,000 | 17.47 | 4,366,500 |
| 2025-05-12 | Brown Hayden (President & CEO) | Sale | 20,000 | 17.09 | 341,800 |
| 2025-05-12 | Nelson Elizabeth A | Sale | 60,000 | 17.43 | 1,045,559 |
| 2025-05-07 | Brown Hayden (President & CEO) | Sale | 40,000 | 15.92 | 636,960 |
| 2025-03-19 | Bottoms Dave (GM, Marketplace) | Sale | 9,593 | 13.46 | 129,112 |
| 2025-03-19 | Marie Olivier (Chief Accounting Officer) | Sale | 2,587 | 13.46 | 34,828 |
| 2025-03-18 | Bottoms Dave (GM, Marketplace) | Sale | 5,411 | 13.07 | 70,716 |
| 2025-03-18 | Bottoms Dave (GM, Marketplace) | Option Ex | 15,004 | .00 | 0 |
| 2025-03-18 | Gessert Erica (Chief Financial Officer) | Sale | 4,316 | 13.07 | 56,405 |
| 2025-03-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 8,433 | .00 | 0 |
| 2025-03-18 | Marie Olivier (Chief Accounting Officer) | Sale | 1,460 | 13.07 | 19,080 |
| 2025-03-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 4,047 | .00 | 0 |
| 2025-03-18 | Brown Hayden (President & CEO) | Sale | 9,075 | 13.07 | 118,601 |
| 2025-03-18 | Brown Hayden (President & CEO) | Option Ex | 17,733 | .00 | 0 |
| 2025-03-07 | Brown Hayden (President & CEO) | Sale | 60,000 | 14.20 | 851,940 |
| 2025-02-19 | Bottoms Dave (GM, VP Marketplace) | Sale | 2,207 | 17.69 | 39,048 |
| 2025-02-19 | Marie Olivier (Chief Accounting Officer) | Sale | 1,546 | 17.71 | 27,378 |
| 2025-02-19 | Nelson Elizabeth A | Sale | 75,000 | 17.79 | 1,334,100 |
| 2025-02-19 | Nelson Elizabeth A | Option Ex | 75,000 | 3.67 | 275,250 |
| 2025-02-18 | Bottoms Dave (GM, VP Marketplace) | Sale | 1,543 | 16.15 | 24,920 |
| 2025-02-18 | Bottoms Dave (GM, VP Marketplace) | Option Ex | 3,750 | .00 | 0 |
| 2025-02-18 | Gessert Erica (Chief Financial Officer) | Sale | 13,765 | 16.15 | 222,304 |
| 2025-02-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 37,500 | .00 | 0 |
| 2025-02-18 | Marie Olivier (Chief Accounting Officer) | Sale | 1,081 | 16.15 | 17,461 |
| 2025-02-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 2,627 | .00 | 0 |
| 2025-02-18 | Brown Hayden (President & CEO) | Sale | 21,122 | 16.15 | 341,120 |
| 2025-02-18 | Brown Hayden (President & CEO) | Option Ex | 58,049 | .00 | 0 |
| 2025-02-14 | Marie Olivier (Chief Accounting Officer) | Sale | 335 | 16.48 | 5,520 |
| 2025-01-21 | Marie Olivier (Chief Accounting Officer) | Sale | 257 | 16.00 | 4,112 |
| 2025-01-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 592 | .00 | 0 |
| 2024-12-19 | Bottoms Dave (GM VP II, Marketplace) | Sale | 9,642 | 16.23 | 156,470 |
| 2024-12-19 | Marie Olivier (Chief Accounting Officer) | Sale | 2,601 | 16.23 | 42,206 |
| 2024-12-18 | Bottoms Dave (GM VP II, Marketplace) | Sale | 5,360 | 17.11 | 91,693 |
| 2024-12-18 | Bottoms Dave (GM VP II, Marketplace) | Option Ex | 15,002 | .00 | 0 |
| 2024-12-18 | Gessert Erica (Chief Financial Officer) | Sale | 4,279 | 17.11 | 73,196 |
| 2024-12-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 8,433 | .00 | 0 |
| 2024-12-18 | Marie Olivier (Chief Accounting Officer) | Sale | 1,448 | 17.11 | 24,773 |
| 2024-12-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 4,049 | .00 | 0 |
| 2024-12-18 | Brown Hayden (President & CEO) | Sale | 8,997 | 17.12 | 154,064 |
| 2024-12-18 | Brown Hayden (President & CEO) | Option Ex | 17,733 | .00 | 0 |
| 2024-12-18 | Nelson Elizabeth A | Sale | 75,000 | 17.37 | 1,302,750 |
| 2024-12-18 | Nelson Elizabeth A | Option Ex | 75,000 | 3.67 | 275,250 |
| 2024-12-16 | Brown Hayden (President & CEO) | Sale | 20,000 | 16.84 | 336,880 |
| 2024-12-09 | Brown Hayden (President & CEO) | Option Ex | 68,199 | 3.68 | 250,972 |
| 2024-11-27 | Brown Hayden (President & CEO) | Sale | 15,000 | 17.00 | 255,000 |
| 2024-11-19 | Bottoms Dave (GM VP II, Marketplace) | Sale | 2,354 | 14.90 | 35,074 |
| 2024-11-19 | Marie Olivier (Chief Accounting Officer) | Sale | 1,649 | 14.90 | 24,576 |
| 2024-11-18 | Bottoms Dave (GM VP II, Marketplace) | Sale | 1,396 | 15.13 | 21,120 |
| 2024-11-18 | Bottoms Dave (GM VP II, Marketplace) | Option Ex | 3,750 | .00 | 0 |
| 2024-11-18 | Gessert Erica (Chief Financial Officer) | Sale | 19,816 | 15.13 | 299,796 |
| 2024-11-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 37,500 | .00 | 0 |
| 2024-11-18 | Marie Olivier (Chief Accounting Officer) | Sale | 978 | 15.13 | 14,796 |
| 2024-11-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 2,627 | .00 | 0 |
| 2024-11-18 | Brown Hayden (President & CEO) | Sale | 30,672 | 15.13 | 464,036 |
| 2024-11-18 | Brown Hayden (President & CEO) | Option Ex | 58,043 | .00 | 0 |
| 2024-11-15 | Bottoms Dave (GM VP II, Marketplace) | Sale | 983 | 14.94 | 14,682 |
| 2024-11-08 | Bottoms Dave (GM VP II, Marketplace) | Sale | 10,508 | 15.86 | 166,688 |
| 2024-11-08 | Marie Olivier (Chief Accounting Officer) | Sale | 9,153 | 15.92 | 145,715 |
| 2024-11-08 | Brown Hayden (President & CEO) | Sale | 10,000 | 15.85 | 158,460 |
| 2024-10-18 | Marie Olivier (Chief Accounting Officer) | Sale | 223 | 10.30 | 2,297 |
| 2024-10-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 591 | .00 | 0 |
| 2024-09-19 | Bottoms Dave (GM VP II, Marketplace) | Sale | 4,688 | 10.74 | 50,339 |
| 2024-09-19 | Marie Olivier (Chief Accounting Officer) | Sale | 2,529 | 10.74 | 27,156 |
| 2024-09-18 | Bottoms Dave (GM VP II, Marketplace) | Sale | 5,626 | 10.57 | 59,472 |
| 2024-09-18 | Bottoms Dave (GM VP II, Marketplace) | Option Ex | 15,004 | .00 | 0 |
| 2024-09-18 | Gessert Erica (Chief Financial Officer) | Sale | 4,491 | 10.57 | 47,474 |
| 2024-09-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 8,433 | .00 | 0 |
| 2024-09-18 | Marie Olivier (Chief Accounting Officer) | Sale | 1,518 | 10.57 | 16,046 |
| 2024-09-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 4,047 | .00 | 0 |
| 2024-09-18 | Brown Hayden (President & CEO) | Sale | 9,444 | 10.57 | 99,832 |
| 2024-09-18 | Brown Hayden (President & CEO) | Option Ex | 17,733 | .00 | 0 |
| 2024-09-18 | Nelson Elizabeth A | Sale | 75,000 | 10.54 | 790,425 |
| 2024-09-18 | Nelson Elizabeth A | Option Ex | 75,000 | 3.67 | 275,250 |
| 2024-09-16 | Brown Hayden (President & CEO) | Sale | 20,000 | 10.01 | 200,159 |
| 2024-08-27 | Bottoms Dave (GM VP II, Marketplace) | Sale | 5,818 | 9.81 | 57,062 |
| 2024-08-20 | Marie Olivier (Chief Accounting Officer) | Sale | 1,622 | 9.44 | 15,313 |
| 2024-08-19 | Bottoms Dave (GM VP II, Marketplace) | Sale | 1,433 | 9.65 | 13,825 |
| 2024-08-19 | Gessert Erica (Chief Financial Officer) | Sale | 20,353 | 9.65 | 196,365 |
| 2024-08-19 | Marie Olivier (Chief Accounting Officer) | Sale | 1,005 | 9.65 | 9,696 |
| 2024-08-19 | Brown Hayden (President & CEO) | Sale | 31,506 | 9.65 | 303,969 |
| 2024-08-18 | Bottoms Dave (GM VP II, Marketplace) | Option Ex | 3,750 | .00 | 0 |
| 2024-08-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 37,500 | .00 | 0 |
| 2024-08-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 2,627 | .00 | 0 |
| 2024-08-18 | Brown Hayden (President & CEO) | Option Ex | 58,046 | .00 | 0 |
| 2024-08-12 | Marie Olivier (Chief Accounting Officer) | Sale | 366 | 9.23 | 3,378 |
| 2024-07-18 | Marie Olivier (Chief Accounting Officer) | Sale | 225 | 11.40 | 2,565 |
| 2024-07-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 591 | .00 | 0 |
| 2024-06-20 | Brown Hayden (President & CEO) | Sale | 9,541 | 10.22 | 97,480 |
| 2024-06-18 | Bottoms Dave (GM VP II, Marketplace) | Sale | 5,684 | 10.22 | 58,073 |
| 2024-06-18 | Bottoms Dave (GM VP II, Marketplace) | Option Ex | 15,003 | .00 | 0 |
| 2024-06-18 | Gessert Erica (Chief Financial Officer) | Sale | 4,537 | 10.22 | 46,354 |
| 2024-06-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 8,432 | .00 | 0 |
| 2024-06-18 | Marie Olivier (Chief Accounting Officer) | Sale | 1,535 | 10.22 | 15,683 |
| 2024-06-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 4,049 | .00 | 0 |
| 2024-06-18 | Brown Hayden (President & CEO) | Option Ex | 17,733 | .00 | 0 |
| 2024-06-17 | Brown Hayden (President & CEO) | Sale | 20,000 | 10.23 | 204,620 |
| 2024-05-29 | Bottoms Dave (GM VP II, Marketplace) | Sale | 1,163 | 10.79 | 12,551 |
| 2024-05-22 | Marie Olivier (Chief Accounting Officer) | Sale | 1,629 | 11.52 | 18,766 |
| 2024-05-21 | Bottoms Dave (GM VP II, Marketplace) | Sale | 1,163 | 11.61 | 13,501 |
| 2024-05-20 | Bottoms Dave (GM VP II, Marketplace) | Sale | 2,379 | 11.76 | 27,986 |
| 2024-05-20 | Gessert Erica (Chief Financial Officer) | Sale | 69,940 | 11.61 | 811,933 |
| 2024-05-20 | Marie Olivier (Chief Accounting Officer) | Sale | 998 | 11.61 | 11,585 |
| 2024-05-20 | Brown Hayden (President & CEO) | Sale | 31,300 | 11.61 | 363,361 |
| 2024-05-20 | Nelson Elizabeth A | Sale | 70,000 | 11.79 | 825,160 |
| 2024-05-20 | Nelson Elizabeth A | Option Ex | 70,000 | 3.67 | 256,900 |
| 2024-05-18 | Bottoms Dave (GM VP II, Marketplace) | Option Ex | 3,750 | .00 | 0 |
| 2024-05-18 | Gessert Erica (Chief Financial Officer) | Option Ex | 150,000 | .00 | 0 |
| 2024-05-18 | Marie Olivier (Chief Accounting Officer) | Option Ex | 2,627 | .00 | 0 |
| 2024-05-18 | Brown Hayden (President & CEO) | Option Ex | 58,042 | .00 | 0 |
| 2024-05-16 | Marie Olivier (Chief Accounting Officer) | Sale | 3,106 | 12.13 | 37,681 |
| 2024-05-03 | Bottoms Dave (GM VP II, Marketplace) | Sale | 2,843 | 13.22 | 37,584 |
Insider trading activities including stock purchases, stock sales, and option exercises of UPWK listed in the above tables cannot be completely guaranteed as to their accuracy. For more insider trading information of Upwork, Inc (symbol UPWK, CIK number 1627475) see the Securities and Exchange Commission (SEC) website.