UPWK insider trading — Upwork, Inc
Over the last 90 days, insiders at Upwork, Inc (UPWK) made 0 open-market purchases worth $0 and 7 open-market sales worth $892K, making them net sellers by $892K. The largest sale was by Kappus Anthony Ray (GM & Chief Operating Officer), who sold 45,732 shares for $386K on Sep 18, 2026.
Updated Oct 16, 2026.
Recent UPWK insider transactions
Every Form 4 filed by Upwork, Inc officers, directors and 10% owners in the last 90 days, newest first. P = open-market purchase, S = open-market sale; other codes are awards, option exercises, tax withholding or gifts.
| Trade date | Insider | Role | Type | Ownership | Shares | Price | Value | Filing |
|---|---|---|---|---|---|---|---|---|
| Sep 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | M · Option exercise | Direct | 114,860 | — | — | Form 4 |
| Sep 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | S · Sale | Direct | 45,732 | $8.45 | $386K | Form 4 |
| Sep 18, 2026 | Mekhalfa Sabrina | Chief Accounting Officer | M · Option exercise | Direct | 3,578 | — | — | Form 4 |
| Sep 18, 2026 | Mekhalfa Sabrina | Chief Accounting Officer | S · Sale | Direct | 1,299 | $8.45 | $11K | Form 4 |
| Sep 18, 2026 | Brown Hayden | President & CEO | M · Option exercise | Direct | 46,410 | — | — | Form 4 |
| Sep 18, 2026 | Brown Hayden | President & CEO | S · Sale | Direct | 23,893 | $8.45 | $202K | Form 4 |
| Sep 18, 2026 | Gessert Erica | Chief Financial Officer | M · Option exercise | Direct | 18,133 | — | — | Form 4 |
| Sep 18, 2026 | Gessert Erica | Chief Financial Officer | S · Sale | Direct | 9,336 | $8.45 | $79K | Form 4 |
| Aug 18, 2026 | Brown Hayden | President & CEO | M · Option exercise · 10b5-1 | Direct | 46,822 | — | — | Form 4 |
| Aug 18, 2026 | Brown Hayden | President & CEO | S · Sale · 10b5-1 | Direct | 73,241 | $8.43 | $617K | Form 4 |
| Aug 18, 2026 | Gessert Erica | Chief Financial Officer | M · Option exercise | Direct | 46,024 | — | — | Form 4 |
| Aug 18, 2026 | Gessert Erica | Chief Financial Officer | S · Sale | Direct | 22,844 | $8.43 | $192K | Form 4 |
| Aug 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | M · Option exercise | Direct | 5,115 | — | — | Form 4 |
| Aug 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | S · Sale | Direct | 1,964 | $8.43 | $17K | Form 4 |
| Jul 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | M · Option exercise | Direct | 1,412 | — | — | Form 4 |
| Jul 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | S · Sale | Direct | 558 | $9.06 | $5K | Form 4 |
UPWK insider trading FAQ
Are insiders buying UPWK stock?
Not on the open market. In the last 90 days, Upwork, Inc insiders made no open-market purchases, and 7 open-market sales totaling $892K. Purchases with the insider's own money are generally seen as a stronger signal than sales, which happen for many reasons (taxes, diversification, planned 10b5-1 sales).
Who are the insiders trading UPWK?
Recent sellers: Brown Hayden, Gessert Erica, Kappus Anthony Ray, Mekhalfa Sabrina.
Where does UPWK insider trading data come from?
Every transaction comes from SEC Form 4 filings on EDGAR. Company officers, directors and 10% owners must file a Form 4 within two business days of buying or selling. InsiderBolt reads these filings directly from the SEC.
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Insider trading data is for informational purposes only and is not investment advice. Filings can be amended; always confirm details on SEC EDGAR.