Upwork Inc (UPWK) insider trading
Recent insider transactions reported to the SEC on Form 4 — directors and officers buying or selling their own company’s stock. Sourced directly from public SEC filings, latest filed Sep 22, 2026.
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- Filings shown
- 23
- Open-market buys
- 0
- Open-market sells
- 17
Counts cover the 23 most recent Form 4 filings Tradune holds for UPWK (filed Mar 20 – Sep 22, 2026); the score below covers only the trailing 90 days (0 buys, 8 sells). No completed check of UPWK's Form 4 list on SEC EDGAR is on record yet; the latest UPWK filing Tradune holds was filed Sep 22, 2026. This is not guaranteed to be the complete record — see UPWK's full Form 4 filing history on SEC EDGAR.
Open-market activity, last 90 days
Purchases (Form 4 code P) and sales (code S) on the 7 filings Tradune holds for UPWK filed Aug 20 – Sep 22, 2026. Grants, exercises, tax withholding and the other Form 4 transaction codes are left out.
8 open-market sales by Rule 10b5-1 checkbox
- On filings with the 10b5-1 box checked
- 2 sales· 73,241 sh
- checkbox disclosed
- On filings with the box not checked
- 6 sales· 105,068 sh
- not proof that no plan exists
- Not comparable
- 0 sales· 0 sh
- filed before Apr 1, 2023, or no checkbox value in the filing data
Counts are Form 4 lines as filed. The checkbox is one per filing, so every sale on a filing with the box checked is counted there even if only some of its transactions were under a plan; it records what the filer disclosed, and the three categories are not a judgement about why a sale was made.
| Insider | Buys | Sells | Shares bought | Shares sold | Value |
|---|---|---|---|---|---|
| Hayden BrownPresident & CEO | 0 | 3 | — | 97,134 | −$819,094 |
| Anthony Ray KappusGM & Chief Operating Officer | 0 | 2 | — | 47,696 | −$403,020 |
| Erica GessertChief Financial Officer | 0 | 2 | — | 32,180 | −$271,373 |
| Sabrina MekhalfaChief Accounting Officer | 0 | 1 | — | 1,299 | −$10,978 |
Value = shares × the price reported on each Form 4 (+ purchases, − sales); every open-market line in this window disclosed a price.
Summarises ~90 days of public SEC Form 4 activity — more distinct buyers, officer involvement and net buying score higher. A description of filing activity, not a rating or buy signal. How this score is computed →
How to read this: an open-market purchase (Form 4 code P) is a buy at the market price with the insider’s own money, as opposed to a grant, award or option exercise; an open-market sale is code S. When two or more distinct insiders report open-market purchases in the same 90-day window, this site labels that a cluster — a definition, not a forecast; see insider cluster buying. “Held after” is Form 4 Table I column 5; “Change” = shares ÷ holdings before the trade (held after − shares for an acquisition, held after + shares for a disposition).
Insider Buying at UPWK
No open-market insider purchases (Form 4 code P) were reported for UPWK between Mar 20, 2026 and Sep 22, 2026. The filings below may include other transaction types — sales, grants, option exercises, and tax withholding — shown for completeness; they are not open-market purchases.
Recent Form 4 filings
Source: SEC EDGAR Form 4 · transaction codes explained
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 8,433 | — | 373,222 | +2.3% | Sep 18, 2026 |
| Option exercise | 9,700 | — | 382,922 | +2.6% | Sep 18, 2026 |
| Open-market sale 10b5-1 box not checked | 9,336 | $8.45 | 373,586 | −2.4% | Sep 18, 2026 |
| Option exercise Restricted Stock Units | 8,433 | — | — | — | Sep 18, 2026 |
| Option exercise Restricted Stock Units | 9,700 | — | — | — | Sep 18, 2026 |
† change in this filer’s own reported holding line (Form 4 Table I, col. 5), not of total company ownership; small prior holdings produce large percentages, so under 100 shares the prior holding is shown instead.
“10b5-1 box checked” = the filer checked the Form 4 box stating that a transaction on the filing was made under a plan intended to satisfy Rule 10b5-1(c); “10b5-1 box not checked” = the box was left blank, which does not prove that no plan exists. The box applies to Form 4s filed from April 1, 2023; older filings, and boxes we could not read, carry no tag. What the 10b5-1 box means.
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Open-market sale 10b5-1 box not checked | 1,299 | $8.45 | 6,675 | −16% | Sep 18, 2026 |
| Option exercise Restricted Stock Units | 3,578 | — | — | — | Sep 18, 2026 |
| Option exercise | 3,578 | — | 7,974 | +81% | Sep 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 114,860 | — | 122,074 | +1,592% | Sep 18, 2026 |
| Open-market sale 10b5-1 box not checked | 45,732 | $8.45 | 76,342 | −37% | Sep 18, 2026 |
| Option exercise Restricted Stock Units | 114,860 | — | — | — | Sep 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 17,733 | — | 788,809 | +2.3% | Sep 18, 2026 |
| Option exercise | 28,677 | — | 817,486 | +3.6% | Sep 18, 2026 |
| Open-market sale 10b5-1 box not checked | 23,893 | $8.45 | 793,593 | −2.9% | Sep 18, 2026 |
| Option exercise Restricted Stock Units | 17,733 | — | — | — | Sep 18, 2026 |
| Option exercise Restricted Stock Units | 28,677 | — | — | — | Sep 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 37,500 | — | 379,109 | +11% | Aug 18, 2026 |
| Option exercise | 8,524 | — | 387,633 | +2.2% | Aug 18, 2026 |
| Open-market sale 10b5-1 box not checked | 22,844 | $8.43 | 364,789 | −5.9% | Aug 18, 2026 |
| Option exercise Restricted Stock Units | 37,500 | — | — | — | Aug 18, 2026 |
| Option exercise Restricted Stock Units | 8,524 | — | — | — | Aug 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 5,115 | — | 9,178 | +126% | Aug 18, 2026 |
| Option exercise Restricted Stock Units | 5,115 | — | — | — | Aug 18, 2026 |
| Open-market sale 10b5-1 box not checked | 1,964 | $8.43 | 7,214 | −21% | Aug 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 18,333 | — | 830,678 | +2.3% | Aug 18, 2026 |
| Option exercise | 13,639 | — | 844,317 | +1.6% | Aug 18, 2026 |
| Open-market sale 10b5-1 box checked | 23,241 | $8.43 | 821,076 | −2.8% | Aug 18, 2026 |
| Open-market sale 10b5-1 box checked | 50,000 | $8.43 | 771,076 | −6.1% | Aug 18, 2026 |
| Option exercise Restricted Stock Units | 14,850 | — | — | — | Aug 18, 2026 |
| Option exercise | 14,850 | — | 812,345 | +1.9% | Aug 18, 2026 |
| Option exercise Restricted Stock Units | 18,333 | — | — | — | Aug 18, 2026 |
| Option exercise Restricted Stock Units | 13,639 | — | — | — | Aug 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 1,412 | — | 4,621 | +44% | Jul 18, 2026 |
| Option exercise Restricted Stock Units | 1,412 | — | — | — | Jul 18, 2026 |
| Open-market sale 10b5-1 box not checked | 558 | $9.06 | 4,063 | −12% | Jul 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise Restricted Stock Units | 9,700 | — | — | — | Jun 18, 2026 |
| Option exercise | 8,432 | — | 341,078 | +2.5% | Jun 18, 2026 |
| Option exercise | 9,700 | — | 350,778 | +2.8% | Jun 18, 2026 |
| Open-market sale 10b5-1 box not checked | 9,169 | $8.15 | 341,609 | −2.6% | Jun 18, 2026 |
| Option exercise Restricted Stock Units | 8,432 | — | — | — | Jun 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 3,577 | — | 5,672 | +171% | Jun 18, 2026 |
| Open-market sale 10b5-1 box not checked | 1,276 | $8.15 | 4,396 | −22% | Jun 18, 2026 |
| Option exercise Restricted Stock Units | 3,577 | — | — | — | Jun 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 17,733 | — | 792,285 | +2.3% | Jun 18, 2026 |
| Option exercise | 28,678 | — | 820,963 | +3.6% | Jun 18, 2026 |
| Open-market sale 10b5-1 box not checked | 23,468 | $8.15 | 797,495 | −2.9% | Jun 18, 2026 |
| Option exercise Restricted Stock Units | 17,733 | — | — | — | Jun 18, 2026 |
| Option exercise Restricted Stock Units | 28,678 | — | — | — | Jun 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award | 45,146 | — | 45,146 | — | Jun 4, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award | 6,207 | — | 91,336 | +7.3% | Jun 4, 2026 |
| Grant / award | 20,880 | — | 112,216 | +23% | Jun 4, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award | 20,880 | — | 56,835 | +58% | Jun 4, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award | 6,207 | — | 45,542 | +16% | Jun 4, 2026 |
| Grant / award | 20,880 | — | 66,422 | +46% | Jun 4, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award | 45,146 | — | 45,146 | — | Jun 4, 2026 |
| Grant / award | 20,880 | — | 66,026 | +46% | Jun 4, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award | 6,207 | — | 126,336 | +5.2% | Jun 4, 2026 |
| Grant / award | 20,880 | — | 147,216 | +17% | Jun 4, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award | 20,880 | — | 52,296 | +66% | Jun 4, 2026 |
| Grant / award | 6,772 | — | 31,416 | +27% | Jun 4, 2026 |
| Grant / award | 6,207 | — | 24,644 | +34% | Jun 4, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 37,500 | — | 346,284 | +12% | May 18, 2026 |
| Option exercise | 8,524 | — | 354,808 | +2.5% | May 18, 2026 |
| Open-market sale 10b5-1 box not checked | 22,162 | $8.66 | 332,646 | −6.2% | May 18, 2026 |
| Option exercise Restricted Stock Units | 37,500 | — | — | — | May 18, 2026 |
| Option exercise Restricted Stock Units | 8,524 | — | — | — | May 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Option exercise | 5,114 | — | 5,114 | — | May 18, 2026 |
| Open-market sale 10b5-1 box not checked | 1,905 | $8.66 | 3,209 | −37% | May 18, 2026 |
| Option exercise Restricted Stock Units | 5,114 | — | — | — | May 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Open-market sale 10b5-1 box checked | 50,000 | $8.57 | 774,552 | −6.1% | May 18, 2026 |
| Option exercise Restricted Stock Units | 14,850 | — | — | — | May 18, 2026 |
| Option exercise Restricted Stock Units | 18,334 | — | — | — | May 18, 2026 |
| Option exercise | 14,850 | — | 815,126 | +1.9% | May 18, 2026 |
| Option exercise | 18,334 | — | 833,460 | +2.2% | May 18, 2026 |
| Option exercise | 13,638 | — | 847,098 | +1.6% | May 18, 2026 |
| Open-market sale 10b5-1 box checked | 22,546 | $8.66 | 824,552 | −2.7% | May 18, 2026 |
| Option exercise Restricted Stock Units | 13,638 | — | — | — | May 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Grant / award Restricted Stock Units | 22,603 | — | — | — | Apr 18, 2026 |
| Transaction | Shares | Price | Held after | Change† | Date |
|---|---|---|---|---|---|
| Open-market sale 10b5-1 box not checked | 9,278 | $12.31 | 307,240 | −2.9% | Mar 18, 2026 |
| Option exercise Restricted Stock Units | 9,699 | — | — | — | Mar 18, 2026 |
| Option exercise | 8,433 | — | 306,819 | +2.8% | Mar 18, 2026 |
| Option exercise | 9,699 | — | 316,518 | +3.2% | Mar 18, 2026 |
| Option exercise Restricted Stock Units | 8,433 | — | — | — | Mar 18, 2026 |
Insider filings reported around the same time
Other companies whose most recent Form 4 was filed closest to UPWK's (Sep 22, 2026).
Frequently asked about UPWK insider activity
How many insiders bought UPWK stock in these Form 4 filings?
No open-market purchases (Form 4 code P) of UPWK shares were reported by Upwork Inc insiders between Mar 20, 2026 and Sep 22, 2026. The 23 filings shown on this page cover other transaction types — sales, grants, option exercises, and tax withholding.
Who filed the most recent Form 4 for UPWK?
The most recent Form 4 on this page was filed by Hayden Brown (President & CEO) on Sep 22, 2026, reporting 5 transactions. The original document is linked from the filing list above on SEC EDGAR. Amended filings (Form 4/A) may later revise reported figures.
What was the largest open-market UPWK insider sale shown?
The largest open-market sale among the filings shown was 50,000 UPWK shares at $8.57 (about $428,475) by Hayden Brown (President & CEO) on May 18, 2026. Value is shares × the price reported on the Form 4; that Form 4 has the Rule 10b5-1 box checked.
New to Form 4s? The transaction codes, the 90-day window and the 0–100 score are defined on the insider-activity score methodology page.
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Track UPWK insider filings free →This score summarizes SEC Form 4 filing activity over the trailing 90 days. It is descriptive, not predictive — not a rating, recommendation, or investment advice. Data: SEC EDGAR (public domain), as filed; amendments may revise figures. Tradune is not a registered investment adviser.
Data as filed; amended filings (Form 4/A) may revise figures. Sales may occur under prearranged Rule 10b5-1 trading plans.