Upwork Inc. (UPWK) Insider Trading
Over the last 3 months, UPWK insiders made 0 open-market buys and 9 sales, a net sale of -$1.5M (SEC Form 4). Over the last 6 months, 256 institutions increased and 177 reduced their position (13F).
Insider Activity
Sentiment
0/100
Buys (3m)
0
Sells (3m)
9
Net (3m)
-$1.5M
Insider trades by month Buys Sells
Sep
Nov
Dec
Feb
Mar
May
Context3-month price -36.3%Institutions accumulating (13F)
| Date | Insider | Type | Shares | Price |
|---|---|---|---|---|
| May 20, 2026 | Brown Haydendirector, officer: President & CEO | Sell | 50,000 | $8.57 |
| May 20, 2026 | Brown Haydendirector, officer: President & CEO | Option | 14,850 | — |
| May 20, 2026 | Gessert Ericaofficer: Chief Financial Officer | Option | 37,500 | — |
| May 20, 2026 | Brown Haydendirector, officer: President & CEO | Option | 13,638 | — |
| May 20, 2026 | Gessert Ericaofficer: Chief Financial Officer | Option | 8,524 | — |
| May 20, 2026 | Brown Haydendirector, officer: President & CEO | Sell | 22,546 | $8.66 |
| May 20, 2026 | Brown Haydendirector, officer: President & CEO | Option | 18,334 | — |
| May 20, 2026 | Gessert Ericaofficer: Chief Financial Officer | Sell | 22,162 | $8.66 |
| May 20, 2026 | Kappus Anthony Rayofficer: GM & Chief Operating Officer | Sell | 1,905 | $8.66 |
| May 20, 2026 | Kappus Anthony Rayofficer: GM & Chief Operating Officer | Option | 5,114 | — |
| Apr 21, 2026 | Kappus Anthony Rayofficer: GM & Chief Operating Officer | Grant | 22,603 | — |
| Mar 20, 2026 | Brown Haydendirector, officer: President & CEO | Sell | 23,745 | $12.31 |
| Mar 20, 2026 | Gessert Ericaofficer: Chief Financial Officer | Option | 9,699 | — |
| Mar 20, 2026 | Bottoms Daveofficer: GM, Marketplace | Sell | 11,575 | $12.31 |
| Mar 20, 2026 | Bottoms Daveofficer: GM, Marketplace | Sell | 7,000 | $11.49 |
| Mar 20, 2026 | Brown Haydendirector, officer: President & CEO | Option | 17,733 | — |
| Mar 20, 2026 | Gessert Ericaofficer: Chief Financial Officer | Sell | 9,278 | $12.31 |
| Mar 20, 2026 | Bottoms Daveofficer: GM, Marketplace | Option | 5,904 | — |
| Mar 20, 2026 | Bottoms Daveofficer: GM, Marketplace | Option | 8,980 | — |
| Mar 20, 2026 | Gessert Ericaofficer: Chief Financial Officer | Option | 8,433 | — |
| Mar 20, 2026 | Mekhalfa Sabrinaofficer: Chief Accounting Officer | Sell | 1,482 | $12.31 |
| Mar 20, 2026 | Brown Haydendirector, officer: President & CEO | Option | 28,677 | — |
| Mar 20, 2026 | Bottoms Daveofficer: GM, Marketplace | Option | 6,024 | — |
| Mar 20, 2026 | Mekhalfa Sabrinaofficer: Chief Accounting Officer | Option | 3,577 | — |
| Feb 19, 2026 | Bottoms Daveofficer: GM, Marketplace | Sell | 17,013 | $13.80 |
| Feb 19, 2026 | Brown Haydendirector, officer: President & CEO | Option | 18,333 | — |
| Feb 19, 2026 | Bottoms Daveofficer: GM, Marketplace | Grant | 81,833 | — |
| Feb 19, 2026 | Brown Haydendirector, officer: President & CEO | Option | 127,678 | — |
| Feb 19, 2026 | Brown Haydendirector, officer: President & CEO | Option | 14,850 | — |
| Feb 19, 2026 | Brown Haydendirector, officer: President & CEO | Grant | 218,221 | — |
Source: UPWK SEC Form 4 filings, latest May 20, 2026. For informational purposes only — not investment advice.
Institutional activity (13F)
How institutions changed their UPWK positions over the last 6 months (SEC Form 13F).
Increased
256
New positions
123
Reduced
177
Sold out
100
Largest moves
| Institution | Action | Shares | Filed |
|---|---|---|---|
| BLACKROCK, INC. | Increased | 20.1M | Feb 12, 2026 |
| PRICE T ROWE ASSOCIATES INC /MD/ | Increased | 19.2M | Feb 17, 2026 |
| BLACKROCK, INC. | Reduced | 18.9M | May 13, 2026 |
| PRICE T ROWE ASSOCIATES INC /MD/ | Reduced | 17.4M | May 15, 2026 |
| VANGUARD GROUP INC | Increased | 15.0M | Jan 29, 2026 |
| VANGUARD PORTFOLIO MANAGEMENT LLC | New Position | 7.8M | May 8, 2026 |
| LSV ASSET MANAGEMENT | Increased | 6.8M | May 11, 2026 |
| LSV ASSET MANAGEMENT | Increased | 6.5M | Feb 6, 2026 |
| ANCIENT ART, L.P. | Increased | 6.0M | May 15, 2026 |
| VANGUARD CAPITAL MANAGEMENT LLC | New Position | 5.6M | May 15, 2026 |
| STATE STREET CORP | Increased | 5.1M | May 15, 2026 |
| STATE STREET CORP | Increased | 4.9M | Feb 13, 2026 |
| CAPITAL INTERNATIONAL INVESTORS | Increased | 4.7M | May 13, 2026 |
| ANCIENT ART, L.P. | Increased | 4.6M | Feb 17, 2026 |
| DIMENSIONAL FUND ADVISORS LP | Increased | 3.7M | May 7, 2026 |
Source: SEC Form 13F filings. For informational purposes only — not investment advice.