UPWK Insider Trading Activity and SEC Form 4 Filings
Trump's trades in UPWK
From his financial disclosures
$15K+
1 purchase
$31K+
3 sales
Sale
May 15, 2026
Reported 47d later
$15K - $50K
Sale
Apr 30, 2026
Reported 62d later
$1K - $15K
Purchase
Mar 30, 2026
Reported 45d later
$15K - $50K
Sale
Feb 26, 2026
Reported 77d later
$15K - $50K
Many orders in these accounts are placed by the account manager.
UPWK insider trading summary
Over the past 12 months, insiders at Upwork, Inc (UPWK) reported 44 sales worth $15.8M by 6 insiders and no open-market purchases on SEC Form 4. Net insider selling was $15.8M.
Latest UPWK insider buys and sells
| Date | Insider | Role | Type | Value |
|---|---|---|---|---|
| Oct 19, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sell | $5K (559 @ $8.43) |
| Sep 18, 2026 | Hayden Brown | President & CEO | Sell | $202K (23,893 @ $8.45) |
| Sep 18, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sell | $386K (45,732 @ $8.45) |
| Sep 18, 2026 | Erica Gessert | Chief Financial Officer | Sell | $79K (9,336 @ $8.45) |
| Sep 18, 2026 | Sabrina Mekhalfa | Chief Accounting Officer | Sell | $11K (1,299 @ $8.45) |
| Aug 18, 2026 | Erica Gessert | Chief Financial Officer | Sell | $192K (22,844 @ $8.43) |
| Aug 18, 2026 | Hayden Brown | President & CEO | Sell | $196K (23,241 @ $8.43) |
| Aug 18, 2026 | Hayden Brown | President & CEO | Sell | $421K (50,000 @ $8.43) |
| Aug 18, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sell | $17K (1,964 @ $8.43) |
| Jul 18, 2026 | Anthony Ray Kappus | GM & Chief Operating Officer | Sell | $5K (558 @ $9.06) |
Source: SEC Form 4 filings. Open-market purchases (code P) and sales (code S) only; option exercises, grants and gifts are excluded.