Upwork Inc. (UPWK) is a publicly traded company in the Unknown sector. Across all available filings, 28 corporate insiders have executed 773 transactions totaling $169.2M, demonstrating a bearish sentiment with -$135.7M in net insider flow. The most recent transaction on Feb 19, 2026 involved a sale of 15,649 shares valued at $211.4K.
No significant insider buying has been recorded for UPWK in the recent period.
No significant insider selling has been recorded for UPWK in the recent period.
Based on recent SEC filings, insider sentiment for UPWK is bearish with an Insider Alignment Score of 10/100 and a net flow of -$135.7M. Insiders are reducing their positions, though this can be driven by factors unrelated to company outlook.
Insider trading at Upwork Inc. (UPWK) refers to stock transactions made by corporate insiders—executives, directors, and beneficial owners holding more than 10% of the company's shares. These individuals have access to material non-public information and are required by law to report their trades to the SEC within two business days. Currently, 28 insiders are actively trading UPWK stock, having executed 773 transactions in the past 90 days. The most active insider is Hayden Brown (Executive), who has made 221 transactions totaling $48.8M.
Get notified when executives and directors at UPWK file new Form 4 transactions
Date | Insider | Title | Type | Shares | Price | Value | Flags |
|---|---|---|---|---|---|---|---|
| Feb 19, 2026 | Bottoms Dave | GM, Marketplace | Sale | 15,649 | $13.51 | $211.4K | |
| Feb 18, 2026 | Bottoms Dave | GM, Marketplace | Award | 81,833 | $N/A | $0 | |
| Feb 18, 2026 | Bottoms Dave | GM, Marketplace | Option Exercise | 3,750 | $N/A | $0 | |
| Feb 18, 2026 | Bottoms Dave | GM, Marketplace | Sale | 17,013 | $13.80 | $234.8K | |
| Feb 18, 2026 | Bottoms Dave | GM, Marketplace | Option Exercise | 3,750 | $N/A | $0 | |
| Feb 18, 2026 | Gessert Erica | Chief Financial Officer | Award | 136,388 | $N/A | $0 | C-Suite |
| Feb 18, 2026 | Gessert Erica | Chief Financial Officer | Option Exercise | 37,500 | $N/A | $0 | C-Suite |
| Feb 18, 2026 | Gessert Erica | Chief Financial Officer | Sale | 26,292 | $13.80 | $362.9K | C-Suite |
| Feb 18, 2026 | Gessert Erica | Chief Financial Officer | Option Exercise | 37,500 | $N/A | $0 | C-Suite |
| Feb 17, 2026 | Bottoms Dave | GM, Marketplace | Option Exercise | 28,912 | $N/A | $0 | |
| Feb 17, 2026 | Bottoms Dave | GM, Marketplace | Option Exercise | 28,912 | $N/A | $0 | |
| Feb 17, 2026 | Gessert Erica | Chief Financial Officer | Option Exercise | 40,477 | $N/A | $0 | C-Suite |
| Feb 17, 2026 | Gessert Erica | Chief Financial Officer | Option Exercise | 40,477 | $N/A | $0 | C-Suite |
| Dec 19, 2025 | Bottoms Dave | Executive | Sale | 9,622 | $20.66 | $198.8K | |
| Dec 18, 2025 | Bottoms Dave | Executive | Sale | 11,285 | $20.59 | $232.4K |
| TYPE | COUNT | VALUE | % |
|---|---|---|---|
Sale(S) | 275 | $152.5M | 79.9% |
Purchase(P) | 14 | $16.8M | 8.8% |
Disposition(D) | 9 | $14.2M | 7.4% |
Exercise(M) | 288 | $7.5M | 3.9% |
Award(A) | 94 | $0 | 0.0% |
Gift(G) | 18 | $0 | 0.0% |
Other(J) | 48 | $0 | 0.0% |
Conversion(C) | 27 | $0 | 0.0% |
Insider selling pressure at Upwork Inc. has increased, with 28 insiders executing 773 transactions across all time. Total sales of $152.5M significantly outpace purchases of $16.8M, resulting in a net outflow of $135.7M. This selling activity appears largely discretionary, which may warrant closer attention from investors.