UPWKIndustrialsSmall-Cap
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 Research Team · SEC Form 4 & insider trading data analysts
Last updated:
Quick Answer
Are UPWK insiders buying or selling?
UPWORK, INC insiders reported 5 open-market buys ($16.8M) and 236 sells ($177.1M) across 241 Form 4 filings — a net selling position of $160.4M.
Source: SEC EDGAR Form 4
Key Statistics (as of Aug 20, 2026)
Total Form 4 filings
241
SEC EDGAR
Insider filers
21
Insider buys (5)
$16.8M
Insider sells (236)
$177.1M
Insider sentiment
Net sellingNet insider flow of $160.4M in net selling.
Recent UPWK insider transactions
| Date | Insider | Role | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| Aug 20, 2026 | Hayden Brown | President & CEO | Sale | 73.2K | $8.43 | $617.2K |
| Aug 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 22.8K | $8.43 | $192.5K |
| Aug 20, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sale | 2.0K | $8.43 | $16.5K |
| Jul 21, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sale | 558 | $9.06 | $5.1K |
| Jun 23, 2026 | Erica Gessert | Chief Financial Officer | Sale | 9.2K | $8.15 | $74.7K |
| Jun 23, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Sale | 1.3K | $8.15 | $10.4K |
| Jun 23, 2026 | Hayden Brown | President & CEO | Sale | 23.5K | $8.15 | $191.3K |
| May 20, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sale | 1.9K | $8.66 | $16.5K |
| May 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 22.2K | $8.66 | $192.0K |
| May 20, 2026 | Hayden Brown | President & CEO | Sale | 72.5K | $8.60 | $623.8K |
| Mar 20, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Sale | 1.5K | $12.31 | $18.2K |
| Mar 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 9.3K | $12.31 | $114.2K |
| Mar 20, 2026 | Hayden Brown | President & CEO | Sale | 23.7K | $12.31 | $292.3K |
| Mar 20, 2026 | Dave Bottoms | GM, Marketplace | Sale | 18.6K | $12.00 | $223.0K |
| Feb 20, 2026 | Erica Gessert | Chief Financial Officer | Sale | 26.3K | $13.80 | $362.9K |
| Feb 20, 2026 | Dave Bottoms | GM, Marketplace | Sale | 32.7K | $13.66 | $446.3K |
| Feb 20, 2026 | Hayden Brown | President & CEO | Sale | 123.2K | $13.80 | $1.7M |
| Dec 22, 2025 | Erica Gessert | Chief Financial Officer | Sale | 9.0K | $20.59 | $186.2K |
| Dec 22, 2025 | Hayden Brown | President & CEO | Sale | 23.1K | $20.59 | $476.6K |
| Dec 22, 2025 | Dave Bottoms | GM, Marketplace | Sale | 20.9K | $20.62 | $431.1K |
| Nov 28, 2025 | Hayden Brown | President & CEO | Sale | 350.0K | $19.51 | $6.8M |
| Nov 25, 2025 | Hayden Brown | President & CEO | Sale | 60.0K | $18.20 | $1.1M |
| Nov 25, 2025 | Gary Steele | Director | Sale | 12.5K | $17.51 | $218.8K |
| Nov 20, 2025 | Hayden Brown | President & CEO | Sale | 24.8K | $16.70 | $415.0K |
| Nov 20, 2025 | Erica Gessert | Chief Financial Officer | Sale | 18.5K | $16.70 | $308.8K |
Showing the 25 most recent of 241 Form 4 filings for UPWORK, INC.
Most active UPWK insiders
- Hayden Brown81 filings
- Olivier Marie48 filings
- Dave Bottoms23 filings
- Erica Gessert19 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?
Across 241 SEC Form 4 filings, UPWORK, INC (UPWK) insiders reported 5 open-market purchases totaling $16.8M and 236 sales totaling $177.1M. That is a net selling position of $160.4M.
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 Aug 20, 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.
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