As of the latest Form 4 filed Jun 23, 2026.
What Upwork Inc insiders — officers, directors and 10% owners — have bought and sold in their own stock, straight from their SEC Form 4 filings. Values are shares × the reported transaction price where both are disclosed.
Buys plotted up, sells down; bar height is the disclosed dollar value (shares × reported price). Our Form 4 history is only complete from mid-2026, so early months are sparse — the series fills in as more filings land. Open-market purchases and sales only.
Newest filing first — the 34 most recent filings for UPWK.
| Filed | Trade date | Insider | Transaction | Shares | Price | Value | 10b5-1 | Filing |
|---|---|---|---|---|---|---|---|---|
| 2026-06-23 | 2026-06-18 | Gessert Erica Chief Financial Officer | SSale | −9.17K | $8.15 | $74.7K | No | Form 4 ↗ |
| 2026-06-23 | 2026-06-18 | Gessert Erica, Chief Financial Officer | MExercise | +9.70K | — | — | No | Form 4 ↗ |
| 2026-06-23 | 2026-06-18 | Gessert Erica, Chief Financial Officer | MExercise | +8.43K | — | — | No | Form 4 ↗ |
| 2026-06-23 | 2026-06-18 | Mekhalfa Sabrina Chief Accounting Officer | SSale | −1.28K | $8.15 | $10.4K | No | Form 4 ↗ |
| 2026-06-23 | 2026-06-18 | Mekhalfa Sabrina, Chief Accounting Officer | MExercise | +3.58K | — | — | No | Form 4 ↗ |
| 2026-06-23 | 2026-06-18 | Brown Hayden President & CEO | SSale | −23.5K | $8.15 | $191K | No | Form 4 ↗ |
| 2026-06-23 | 2026-06-18 | Brown Hayden, President & CEO | MExercise | +28.7K | — | — | No | Form 4 ↗ |
| 2026-06-23 | 2026-06-18 | Brown Hayden, President & CEO | MExercise | +17.7K | — | — | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | BRAMLEY CLAIRE Director | AAward | +45.1K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | Steele Gary Director | AAward | +20.9K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | Steele Gary, Director | AAward | +6.21K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | EVAN DANA L Director | AAward | +20.9K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | KELMAN GLENN Director | AAward | +20.9K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | KELMAN GLENN, Director | AAward | +6.21K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | LISSY DAVID H Director | AAward | +20.9K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | LISSY DAVID H, Director | AAward | +45.1K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | HARVEY KEVIN Director | AAward | +20.9K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | HARVEY KEVIN, Director | AAward | +6.21K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | LAYTON THOMAS Director | AAward | +20.9K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | LAYTON THOMAS, Director | AAward | +6.77K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-08 | 2026-06-04 | LAYTON THOMAS, Director | AAward | +6.21K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-19 | Bottoms Dave GM, Marketplace | SSale | −7.00K | $11.49 | $80.4K | Yes (planned) | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Bottoms Dave, GM, Marketplace | SSale | −11.6K | $12.31 | $143K | Yes (planned) | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Bottoms Dave, GM, Marketplace | MExercise | +5.90K | — | — | Yes (planned) | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Bottoms Dave, GM, Marketplace | MExercise | +6.02K | — | — | Yes (planned) | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Bottoms Dave, GM, Marketplace | MExercise | +8.98K | — | — | Yes (planned) | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Gessert Erica Chief Financial Officer | SSale | −9.28K | $12.31 | $114K | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Gessert Erica, Chief Financial Officer | MExercise | +9.70K | — | — | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Gessert Erica, Chief Financial Officer | MExercise | +8.43K | — | — | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Mekhalfa Sabrina Chief Accounting Officer | SSale | −1.48K | $12.31 | $18.2K | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Mekhalfa Sabrina, Chief Accounting Officer | MExercise | +3.58K | — | — | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Brown Hayden President & CEO | SSale | −23.7K | $12.31 | $292K | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Brown Hayden, President & CEO | MExercise | +28.7K | — | — | No | Form 4 ↗ |
| 2026-03-20 | 2026-03-18 | Brown Hayden, President & CEO | MExercise | +17.7K | — | — | No | Form 4 ↗ |
Insiders — a company’s officers, directors and holders of more than 10% of its stock — must report any trade in that stock to the SEC on a Form 4 within two business days. Each row here is one transaction from those filings.
The transaction code tells you what happened: Purchase (P) and Sale (S) are open-market trades — the ones markets watch most; Award (A) is a granted stock or unit, Option exercise (M) converts options into shares, and Gift (G) is a transfer for no consideration. Awards, exercises and gifts are largely compensation or administrative, not a directional bet.
One caveat on sales: many are made under a Rule 10b5-1 plan scheduled months in advance, so a sale is not automatically a bearish signal. Insider activity is a noisy input — read it alongside the filings, not on its own.
See also UPWK’s full analysis or the market-wide insider trading feed. The tabs above jump to UPWK’s other SEC data.
Source: SEC Form 4 filings for UPWK, parsed from EDGAR. Transaction prices are as reported in the filing — SEC public-domain data, not market quotes. Values are shares × reported price where both are disclosed; grants and gifts often carry no price. A delayed record of what insiders reported, not a live position or a recommendation.
Research and education only — not financial advice. TENKis not a registered investment adviser or broker-dealer and gives no personalized advice. Every call is impersonal — identical for all users, generated on a schedule from SEC filings plus a delayed/third-party price feed — may be wrong or out of date, and is not a recommendation to buy or sell any security. The operator and an affiliated trading operation may hold or trade the securities TENK rates; see Disclosures. Past performance does not guarantee future results. Do your own research.