UPWORK, INC (UPWK) Insider Transactions
UPWK Insider Buying & Selling Activity
Between Aug 8, 2025 and Aug 18, 2026, 7 insiders at UPWORK, INC (UPWK) reported 47 transactions on record: 0 purchases and 47 sales. In total, insiders bought $0 and sold $18.94M, a net selling position of $18.94M. 3 insiders also sold within a 30-day window around Aug 18, 2026.
Multiple insiders trading the same direction in a short window is generally read as a stronger signal than any single trade alone.
| Date | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| Nov 26, 2025 | Brown Hayden | President & CEO | Sale | 275.0K | $5.34M |
| Feb 18, 2026 | Brown Hayden | President & CEO | Sale | 123.2K | $1.70M |
| Nov 25, 2025 | Brown Hayden | President & CEO | Sale | 75.0K | $1.48M |
| Nov 21, 2025 | Brown Hayden | President & CEO | Sale | 60.0K | $1.09M |
| Aug 15, 2025 | Brown Hayden | President & CEO | Sale | 60.0K | $825.5K |
Every insider with activity on record, most recently active first.
| Insider | Role | Last Activity | Date | Latest Known Holding |
|---|---|---|---|---|
| Brown Hayden | President & CEO | Sale | Aug 18, 2026 | 771.1K |
| Gessert Erica | Chief Financial Officer | Sale | Aug 18, 2026 | 364.8K |
| Kappus Anthony Ray | GM & Chief Operating Officer | Sale | Aug 18, 2026 | 7.2K |
| Mekhalfa Sabrina | Chief Accounting Officer | Sale | Jun 18, 2026 | 4.4K |
| Bottoms Dave | GM, Marketplace | Sale | Mar 19, 2026 | 2.7K |
| Steele Gary | Director | Sale | Nov 21, 2025 | 85.1K |
| Marie Olivier | Chief Accounting Officer | Sale | Aug 19, 2025 | 748 |
Every purchase and sale on record, deduplicated. "52w range" shows where that price sat in the trailing year at the time, and "Since" shows the paper return from that price to today.
| Date | Insider | Role | Type | Shares | Price | Value | 52w Range | Since |
|---|---|---|---|---|---|---|---|---|
| Aug 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | Sale | 2.0K | $8.43 | $16.5K | — | +7.0% |
| Aug 18, 2026 | Gessert Erica | Chief Financial Officer | Sale | 22.8K | $8.43 | $192.5K | — | +7.0% |
| Aug 18, 2026 | Brown Hayden | President & CEO | Sale | 73.2K | $8.43 | $617.2K | — | +7.0% |
| Jul 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | Sale | 558 | $9.06 | $5.1K | — | -0.4% |
| Jun 18, 2026 | Brown Hayden | President & CEO | Sale | 23.5K | $8.15 | $191.3K | 0% | +10.7% |
| Jun 18, 2026 | Mekhalfa Sabrina | Chief Accounting Officer | Sale | 1.3K | $8.15 | $10.4K | 0% | +10.7% |
| Jun 18, 2026 | Gessert Erica | Chief Financial Officer | Sale | 9.2K | $8.15 | $74.7K | 0% | +10.7% |
| May 18, 2026 | Brown Hayden | President & CEO | Sale | 72.5K | $8.60 | $623.8K | 5% | +4.9% |
| May 18, 2026 | Gessert Erica | Chief Financial Officer | Sale | 22.2K | $8.66 | $192.0K | 5% | +4.2% |
| May 18, 2026 | Kappus Anthony Ray | GM & Chief Operating Officer | Sale | 1.9K | $8.66 | $16.5K | 5% | +4.2% |
| Mar 19, 2026 | Bottoms Dave | GM, Marketplace | Sale | 7.0K | $11.49 | $80.4K | 0% | -21.5% |
| Mar 18, 2026 | Bottoms Dave | GM, Marketplace | Sale | 11.6K | $12.31 | $142.5K | 3% | -26.7% |
| Mar 18, 2026 | Brown Hayden | President & CEO | Sale | 23.7K | $12.31 | $292.3K | 3% | -26.7% |
| Mar 18, 2026 | Gessert Erica | Chief Financial Officer | Sale | 9.3K | $12.31 | $114.2K | 3% | -26.7% |
| Mar 18, 2026 | Mekhalfa Sabrina | Chief Accounting Officer | Sale | 1.5K | $12.31 | $18.2K | 3% | -26.7% |
| Feb 19, 2026 | Bottoms Dave | GM, Marketplace | Sale | 15.6K | $13.51 | $211.4K | 15% | -33.2% |
| Feb 18, 2026 | Brown Hayden | President & CEO | Sale | 123.2K | $13.80 | $1.70M | 19% | -34.6% |
| Feb 18, 2026 | Bottoms Dave | GM, Marketplace | Sale | 17.0K | $13.80 | $234.8K | 19% | -34.6% |
| Feb 18, 2026 | Gessert Erica | Chief Financial Officer | Sale | 26.3K | $13.80 | $362.9K | 19% | -34.6% |
| Dec 19, 2025 | Bottoms Dave | GM, Marketplace | Sale | 9.6K | $20.66 | $198.8K | 87% | -56.3% |
| Dec 18, 2025 | Bottoms Dave | GM, Marketplace | Sale | 11.3K | $20.59 | $232.3K | 85% | -56.2% |
| Dec 18, 2025 | Brown Hayden | President & CEO | Sale | 23.1K | $20.59 | $476.6K | 85% | -56.2% |
| Dec 18, 2025 | Gessert Erica | Chief Financial Officer | Sale | 9.0K | $20.59 | $186.2K | 85% | -56.2% |
| Nov 26, 2025 | Brown Hayden | President & CEO | Sale | 275.0K | $19.43 | $5.34M | 94% | -53.6% |
| Nov 25, 2025 | Brown Hayden | President & CEO | Sale | 75.0K | $19.78 | $1.48M | 95% | -54.4% |
| Nov 21, 2025 | Steele Gary | Director | Sale | 12.5K | $17.51 | $218.8K | 74% | -48.5% |
| Nov 21, 2025 | Brown Hayden | President & CEO | Sale | 60.0K | $18.20 | $1.09M | 74% | -50.4% |
| Nov 19, 2025 | Bottoms Dave | GM, Marketplace | Sale | 1.7K | $18.13 | $31.7K | 77% | -50.2% |
| Nov 18, 2025 | Bottoms Dave | GM, Marketplace | Sale | 2.0K | $16.72 | $33.5K | 64% | -46.1% |
| Nov 18, 2025 | Gessert Erica | Chief Financial Officer | Sale | 18.5K | $16.70 | $308.8K | 64% | -46.0% |
| Nov 18, 2025 | Brown Hayden | President & CEO | Sale | 24.8K | $16.70 | $415.0K | 64% | -46.0% |
| Nov 17, 2025 | Bottoms Dave | GM, Marketplace | Sale | 561 | $16.45 | $9.2K | 53% | -45.2% |
| Sep 19, 2025 | Brown Hayden | President & CEO | Sale | 20.0K | $20.00 | $400.0K | 100% | -54.9% |
| Sep 19, 2025 | Bottoms Dave | GM, Marketplace | Sale | 10.0K | $19.96 | $199.9K | 100% | -54.8% |
| Sep 18, 2025 | Brown Hayden | President & CEO | Sale | 42.3K | $19.09 | $808.2K | 100% | -52.8% |
| Sep 18, 2025 | Bottoms Dave | GM, Marketplace | Sale | 10.9K | $19.16 | $208.8K | 100% | -52.9% |
| Sep 18, 2025 | Gessert Erica | Chief Financial Officer | Sale | 8.7K | $19.16 | $167.3K | 100% | -52.9% |
| Sep 17, 2025 | Brown Hayden | President & CEO | Sale | 20.0K | $18.00 | $360.0K | 100% | -49.9% |
| Aug 29, 2025 | Bottoms Dave | GM, Marketplace | Sale | 1.7K | $14.95 | $25.3K | 75% | -39.7% |
| Aug 19, 2025 | Marie Olivier | Chief Accounting Officer | Sale | 1.7K | $13.88 | $23.4K | 56% | -35.0% |
| Aug 18, 2025 | Marie Olivier | Chief Accounting Officer | Sale | 941 | $13.84 | $13.0K | 58% | -34.8% |
| Aug 18, 2025 | Brown Hayden | President & CEO | Sale | 25.6K | $13.84 | $353.9K | 58% | -34.8% |
| Aug 18, 2025 | Bottoms Dave | GM, Marketplace | Sale | 2.1K | $13.84 | $28.5K | 58% | -34.8% |
| Aug 18, 2025 | Gessert Erica | Chief Financial Officer | Sale | 19.0K | $13.84 | $263.4K | 58% | -34.8% |
| Aug 15, 2025 | Brown Hayden | President & CEO | Sale | 60.0K | $13.76 | $825.5K | 56% | -34.4% |
| Aug 14, 2025 | Marie Olivier | Chief Accounting Officer | Sale | 1.3K | $14.00 | $18.1K | 55% | -35.6% |
| Aug 8, 2025 | Bottoms Dave | GM, Marketplace | Sale | 9.0K | $12.88 | $115.9K | 49% | -30.0% |
52w range and paper return are only computed for transactions with a date that lines up with price history on record.
Are insiders buying or selling UPWK stock?
On record between Aug 8, 2025 and Aug 18, 2026, UPWORK, INC insiders made 0 purchases ($0) and 47 sales ($18.94M), a net selling position of $18.94M.
Has there been cluster buying or selling at UPWK?
No buying clusters (2+ insiders within 30 days) on record. 4 insiders sold within 30 days around Aug 29, 2025; 3 insiders sold within 30 days around Sep 19, 2025; 4 insiders sold within 30 days around Nov 26, 2025; 3 insiders sold within 30 days around Dec 19, 2025; 4 insiders sold within 30 days around Mar 19, 2026; 3 insiders sold within 30 days around May 18, 2026; 4 insiders sold within 30 days around Jul 18, 2026; 3 insiders sold within 30 days around Aug 18, 2026.
What is the largest recent insider transaction at UPWK?
The largest transaction on record is Brown Hayden (President & CEO), a sale of $5.34M on Nov 26, 2025.
Does a 10b5-1 automatic trading plan explain UPWK's insider sales?
This data does not indicate whether a given sale was part of a pre-scheduled Rule 10b5-1 plan, that detail is not captured in the transaction data available here.