Insider activity at Upwork, Inc has been all selling for a year now: about $15.8 million from six sellers, and zero buyers at market prices.
Selling on its own is common and often pre-planned (10b5-1 plans, taxes, diversification), so it matters more when it is unusually heavy or broad.
Quarter by quarter: 7 quarters in a row of net selling by insiders. Insiders bought in 0 of the last 7 full quarters. Big money check: 297 institutions held UPWK as of Q2 2026, and more funds bought than sold.
| Filed | Insider | Role | Type | Shares | Price | Value | Source |
|---|---|---|---|---|---|---|---|
| Sep 22, 2026 | Mekhalfa Sabrina | Executive Officer | Sell | 1,299 | $8.45 | $11K | SEC |
| Sep 22, 2026 | Kappus Anthony Ray | COO | Sell | 45,732 | $8.45 | $386K | SEC |
| Sep 22, 2026 | Gessert Erica | CFO | Sell | 9,336 | $8.45 | $79K | SEC |
| Sep 22, 2026 | Brown Hayden | CEO | Sell | 23,893 | $8.45 | $202K | SEC |
| Aug 20, 2026 | Brown Hayden | CEO | Sell | 23,241 | $8.43 | $196K | SEC |
| Aug 20, 2026 | Brown Hayden | CEO | Sell | 50,000 | $8.43 | $422K | SEC |
| Aug 20, 2026 | Gessert Erica | CFO | Sell | 22,844 | $8.43 | $193K | SEC |
| Aug 20, 2026 | Kappus Anthony Ray | COO | Sell | 1,964 | $8.43 | $17K | SEC |
| Jul 21, 2026 | Kappus Anthony Ray | COO | Sell | 558 | $9.06 | $5K | SEC |
| Jun 23, 2026 | Gessert Erica | CFO | Sell | 9,169 | $8.15 | $75K | SEC |
| Jun 23, 2026 | Mekhalfa Sabrina | Executive Officer | Sell | 1,276 | $8.15 | $10K | SEC |
| Jun 23, 2026 | Brown Hayden | CEO | Sell | 23,468 | $8.15 | $191K | SEC |
| May 20, 2026 | Kappus Anthony Ray | COO | Sell | 1,905 | $8.66 | $16K | SEC |
| May 20, 2026 | Gessert Erica | CFO | Sell | 22,162 | $8.66 | $192K | SEC |
| May 20, 2026 | Brown Hayden | CEO | Sell | 22,546 | $8.66 | $195K | SEC |
In the last 12 months Upwork, Inc insiders made open-market purchases worth about $0 and sales worth about $15.8 million. Data comes from SEC Form 4 filings, updated every 30 minutes on CapitalSnitch.
The most recent open-market insider trade in UPWK was filed on 2026-09-22.
297 investment managers reported holding UPWK in SEC Form 13F filings for Q2 2026.
No congressional trades in UPWK were reported in the past two years. The full list is free on CapitalSnitch.
Public-record data for research and education, not investment advice. Insider sales are often pre-planned (10b5-1). Congress data: Data derived from public disclosures filed under the Ethics in Government Act and the STOCK Act, republished free for public transparency and news reporting. Disclosures may lag the trade by 45 days or more and show amounts only as ranges. This data may not be used for credit rating, loan underwriting, solicitation of money (political, charitable or other), direct-mail or commercial targeting (5 U.S.C. 13107).