There have been 50 recent insider transactions recorded for Upwork Inc. (UPWK), including 13 buys and 34 sells. Total insider buying was valued at RSU Award and total insider selling at $6.04M.
Notable insiders with recent activity include Bottoms Dave, Brown Hayden, Mekhalfa Sabrina. Insider transactions can provide insights into how company leadership views the stock's valuation and future prospects.
Insider Transactions — UPWK
| Date |
Name |
Role |
Transaction |
Shares |
Avg. Price |
Value |
Shares Owned |
| 2026-03-19 |
Bottoms Dave |
GM, Marketplace |
Informative Sell |
7,000 |
$11.49 |
$80.45K |
2,678 |
| 2026-03-18 |
Brown Hayden |
President & CEO |
Option Exercise (Sell) |
17,733 |
- |
- |
141,866 |
| 2026-03-18 |
Mekhalfa Sabrina |
Chief Accounting Officer |
Informative Sell |
1,482 |
$12.31 |
$18.25K |
2,095 |
| 2026-03-18 |
Gessert Erica |
Chief Financial Officer |
Option Exercise (Sell) |
8,433 |
- |
- |
67,463 |
| 2026-03-18 |
Bottoms Dave |
GM, Marketplace |
Option Exercise |
8,980 |
- |
- |
9,325 |
| 2026-02-19 |
Bottoms Dave |
GM, Marketplace |
Informative Sell |
15,649 |
$13.51 |
$211.44K |
345 |
| 2026-02-18 |
Brown Hayden |
President & CEO |
Option Exercise (Sell) |
7,611 |
- |
- |
- |
| 2026-02-18 |
Gessert Erica |
Chief Financial Officer |
RSU Award |
136,388 |
- |
- |
136,388 |
| 2026-02-18 |
Bottoms Dave |
GM, Marketplace |
Option Exercise (Sell) |
3,750 |
- |
- |
15,000 |
| 2026-02-17 |
Brown Hayden |
President & CEO |
Option Exercise (Sell) |
127,678 |
- |
- |
- |
| 2026-02-17 |
Gessert Erica |
Chief Financial Officer |
Option Exercise (Sell) |
40,477 |
- |
- |
- |
| 2026-02-17 |
Bottoms Dave |
GM, Marketplace |
Option Exercise (Sell) |
28,912 |
- |
- |
- |
| 2025-12-19 |
Bottoms Dave |
GM, Marketplace |
Informative Sell |
9,622 |
$20.66 |
$198.81K |
345 |
| 2025-12-18 |
Brown Hayden |
President & CEO |
Option Exercise (Sell) |
17,733 |
- |
- |
159,599 |
| 2025-12-18 |
Mekhalfa Sabrina |
Chief Accounting Officer |
RSU Award |
42,929 |
- |
- |
42,929 |
| 2025-12-18 |
Gessert Erica |
Chief Financial Officer |
Option Exercise (Sell) |
8,433 |
- |
- |
75,896 |
| 2025-12-18 |
Bottoms Dave |
GM, Marketplace |
Option Exercise |
8,980 |
- |
- |
9,325 |
| 2025-12-15 |
Mekhalfa Sabrina |
Chief Accounting Officer |
Unknown |
- |
- |
- |
- |
| 2025-11-26 |
Brown Hayden |
President & CEO |
Informative Sell |
100,000 |
$19.44 |
$1.94M |
697,894 |
| 2025-11-25 |
Brown Hayden |
President & CEO |
Informative Sell |
75,000 |
$19.78 |
$1.48M |
972,894 |
| 2025-11-21 |
Steele Gary |
Director |
Informative Sell |
12,500 |
$17.51 |
$218.85K |
85,129 |
| 2025-11-21 |
Brown Hayden |
President & CEO |
Informative Sell |
60,000 |
$18.20 |
$1.09M |
1,047,894 |
| 2025-11-19 |
Bottoms Dave |
GM, Marketplace |
Informative Sell |
1,748 |
$18.13 |
$31.69K |
345 |
| 2025-11-18 |
Bottoms Dave |
GM, Marketplace |
Informative Sell |
1,047 |
$17.24 |
$18.05K |
2,093 |
| 2025-11-18 |
Brown Hayden |
President & CEO |
Option Exercise (Sell) |
7,610 |
- |
- |
7,611 |
| 2025-11-18 |
Gessert Erica |
Chief Financial Officer |
Option Exercise (Sell) |
37,500 |
- |
- |
225,000 |
| 2025-11-17 |
Bottoms Dave |
GM, Marketplace |
Informative Sell |
561 |
$16.45 |
$9.23K |
345 |
| 2025-09-18 |
Gessert Erica |
Chief Financial Officer |
Option Exercise (Sell) |
8,433 |
- |
- |
84,329 |
| 2025-09-18 |
Bottoms Dave |
GM, Marketplace |
Option Exercise |
5,904 |
- |
- |
21,253 |
| 2025-06-23 |
Marie Olivier |
Chief Accounting Officer |
Informative Sell |
1,842 |
$13.24 |
$24.39K |
2,042 |
| 2025-06-20 |
Marie Olivier |
Chief Accounting Officer |
Informative Sell |
748 |
$13.24 |
$9.91K |
3,884 |
| 2025-06-18 |
Brown Hayden |
President & CEO |
Option Exercise (Sell) |
17,733 |
- |
- |
195,066 |
| 2025-06-18 |
Marie Olivier |
Chief Accounting Officer |
Option Exercise |
2,635 |
- |
- |
3,929 |
| 2025-06-18 |
Gessert Erica |
Chief Financial Officer |
Option Exercise (Sell) |
8,433 |
- |
- |
92,762 |
| 2025-06-18 |
Bottoms Dave |
GM, Marketplace |
Option Exercise |
8,980 |
- |
- |
8,980 |
| 2025-06-06 |
Srinivasan Leela |
Director |
Informative Sell |
3,314 |
$15.36 |
$50.89K |
79,469 |
| 2025-06-05 |
Kelman Glenn |
Director |
Unknown |
- |
- |
- |
- |
| 2025-06-05 |
Evan Dana L |
Director |
Unknown |
- |
- |
- |
- |
| 2025-06-05 |
Layton Thomas |
Director |
RSU Award |
11,370 |
- |
- |
32,735 |
| 2025-06-05 |
Harvey Kevin |
Director |
RSU Award |
11,370 |
- |
- |
116,749 |
| 2025-06-05 |
Kelman Glenn |
Director |
RSU Award |
24,585 |
- |
- |
24,585 |
| 2025-06-05 |
Evan Dana L |
Director |
RSU Award |
24,585 |
- |
- |
24,585 |
| 2025-06-05 |
Steele Gary |
Director |
RSU Award |
11,370 |
- |
- |
94,249 |
| 2025-06-05 |
Srinivasan Leela |
Director |
Informative Sell |
6,520 |
$15.16 |
$98.86K |
82,783 |
| 2025-06-05 |
Vazquez-ubarri Anilu |
Director |
RSU Award |
11,370 |
- |
- |
83,968 |
| 2025-05-20 |
Marie Olivier |
Chief Accounting Officer |
Informative Sell |
1,655 |
$16.41 |
$27.15K |
1,294 |
| 2025-05-20 |
Bottoms Dave |
GM, Marketplace |
Informative Sell |
1,620 |
$16.41 |
$26.58K |
- |
| 2025-05-19 |
Brown Hayden |
President & CEO |
Informative Sell |
9,620 |
$16.56 |
$159.33K |
1,130,791 |
| 2025-05-19 |
Marie Olivier |
Chief Accounting Officer |
Informative Sell |
444 |
$16.81 |
$7.46K |
2,949 |
| 2025-05-19 |
Gessert Erica |
Chief Financial Officer |
Informative Sell |
19,677 |
$16.56 |
$325.9K |
181,873 |
■ Informative Buy/Sell — open market transaction (most significant)
■ Uninformative Buy — award, option exercise, conversion
■ Uninformative Sell — tax withholding, award vest sale
■ Neutral — gift, trust, expiry
