UPWORK, INC Insider Trading Activity
Every SEC Form 4 insider transaction reported for UPWORK, INC (UPWK), sourced directly from SEC EDGAR and updated as new filings are accepted.
By Trabud · Insider-trading data from SEC EDGAR
Latest filing:
Compiled automatically from SEC EDGAR Form 4 filings and refreshed daily. Figures count purchases (code P) and sales (code S) only — not grants, option exercises, or gifts. How this page is built. Not investment advice.
Quick Answer
Are UPWK insiders buying or selling?
In the last 12 months, UPWORK, INC insiders reported 0 open-market purchases ($0) and 30 sales ($15.8M) — net selling of $15.8M. Since October 2018, Trabud has recorded 245 Form 4 filings for UPWK: 5 buys ($16.8M) and 240 sells ($177.8M).
Source: SEC EDGAR Form 4
What stands out
- No UPWORK, INC insider made an open-market purchase in the last 12 months; the 30 reported open-market sales totaled $15.8M.
Key Statistics (October 2018 – Sep 22, 2026)
Total Form 4 filings
245
SEC EDGAR
Insider filers
21
Insider buys (5)
$16.8M
Insider sells (240)
$177.8M
Insider sentiment
Net sellingNet insider flow of $161.0M in net selling since October 2018, and $15.8M in net selling over the last 12 months.
Recent UPWK insider transactions
| Date | Insider | Role | Type | Shares | Price | Value | Filing |
|---|---|---|---|---|---|---|---|
| Sep 22, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Sale | 1.3K | $8.45 | $11.0K | SEC ↗ |
| Sep 22, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sale | 45.7K | $8.45 | $386.5K | SEC ↗ |
| Sep 22, 2026 | Erica Gessert | Chief Financial Officer | Sale | 9.3K | $8.45 | $78.9K | SEC ↗ |
| Sep 22, 2026 | Hayden Brown | President & CEO | Sale | 23.9K | $8.45 | $201.9K | SEC ↗ |
| Aug 20, 2026 | Hayden Brown | President & CEO | Sale | 73.2K | $8.43 | $617.2K | SEC ↗ |
| Aug 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 22.8K | $8.43 | $192.5K | SEC ↗ |
| Aug 20, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sale | 2.0K | $8.43 | $16.5K | SEC ↗ |
| Jul 21, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sale | 558 | $9.06 | $5.1K | SEC ↗ |
| Jun 23, 2026 | Erica Gessert | Chief Financial Officer | Sale | 9.2K | $8.15 | $74.7K | SEC ↗ |
| Jun 23, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Sale | 1.3K | $8.15 | $10.4K | SEC ↗ |
| Jun 23, 2026 | Hayden Brown | President & CEO | Sale | 23.5K | $8.15 | $191.3K | SEC ↗ |
| May 20, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sale | 1.9K | $8.66 | $16.5K | SEC ↗ |
| May 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 22.2K | $8.66 | $192.0K | SEC ↗ |
| May 20, 2026 | Hayden Brown | President & CEO | Sale | 72.5K | $8.60 | $623.8K | SEC ↗ |
| Mar 20, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Sale | 1.5K | $12.31 | $18.2K | SEC ↗ |
| Mar 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 9.3K | $12.31 | $114.2K | SEC ↗ |
| Mar 20, 2026 | Hayden Brown | President & CEO | Sale | 23.7K | $12.31 | $292.3K | SEC ↗ |
| Mar 20, 2026 | Dave Bottoms | GM, Marketplace | Sale | 18.6K | $12.00 | $223.0K | SEC ↗ |
| Feb 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 26.3K | $13.80 | $362.9K | SEC ↗ |
| Feb 20, 2026 | Dave Bottoms | GM, Marketplace | Sale | 32.7K | $13.66 | $446.3K | SEC ↗ |
| Feb 20, 2026 | Hayden Brown | President & CEO | Sale | 123.2K | $13.80 | $1.7M | SEC ↗ |
| Dec 22, 2025 | Erica Gessert | Chief Financial Officer | Sale | 9.0K | $20.59 | $186.2K | SEC ↗ |
| Dec 22, 2025 | Hayden Brown | President & CEO | Sale | 23.1K | $20.59 | $476.6K | SEC ↗ |
| Dec 22, 2025 | Dave Bottoms | GM, Marketplace | Sale | 20.9K | $20.62 | $431.1K | SEC ↗ |
| Nov 28, 2025 | Hayden Brown | President & CEO | Sale | 350.0K | $19.51 | $6.8M | SEC ↗ |
Showing the 25 most recent of 245 Form 4 filings for UPWORK, INC.
Most active UPWK insiders
- Hayden Brown82 filings
- Olivier Marie48 filings
- Dave Bottoms23 filings
- Erica Gessert20 filings
- Eric Gilpin16 filings
Ask anything about UPWK insider activity
Use Trabud's AI agent to query UPWORK, INC's Form 4 history in plain English — "Show me UPWK CEO purchases this year" or compare it against any other ticker.
Open the AI agentUPWK insider trading FAQ
Are UPWORK, INC insiders buying or selling?
In the last 12 months, UPWORK, INC insiders reported 0 open-market purchases ($0) and 30 sales ($15.8M) — net selling of $15.8M. Since October 2018, Trabud has recorded 245 Form 4 filings for UPWK: 5 buys ($16.8M) and 240 sells ($177.8M). Over the full record that is net selling of $161.0M.
How many insiders trade UPWK stock?
21 distinct insider filers — officers, directors, 10%+ owners, and investment groups filing jointly — have reported Form 4 transactions for UPWORK, INC. The most recent filing was accepted on Sep 22, 2026.
Where does Trabud get UPWK insider trading data?
All UPWK insider trading data comes directly from official SEC EDGAR Form 4 filings, which corporate insiders must submit within two business days of a transaction under Section 16(a) of the Securities Exchange Act of 1934.