Upwork Inc.
Upwork Inc. (UPWK) Insider Trading
Form 4 buy vs sell counts, ratio, and sentiment — switch this quarter or last 12 months; chart and transactions below.
SEC EDGAR · FMP · UPWK · as of Jun 8, 2026
Activity summary
Buy transactions
0
P-Purchase only
Sell transactions
47
12 Months
Buy/Sell ratio
0.00
Buy/Sell (by trades)
Overall sentiment
Upwork Inc. insiders have been primarily selling shares over the past 12 Months. Selling activity is often driven by pre-scheduled Rule 10b5-1 plans rather than negative sentiment toward the company.
▸ Source: SEC EDGAR · Form 3 & 4 · via Financial Modeling Prep · Buy = P-Purchase only · Sell = S-Sale only
As of Jun 8, 2026
UPWK insider buying and selling by quarter
UPWK insider selling · UPWK insider buying stocks · quarterly insider activity
Mobile shows last 4Q · Desktop shows full 8Q
▸ Source: SEC EDGAR · Form 3 & 4 · via Financial Modeling Prep · last 8 quarters
As of Jun 8, 2026
Active insiders
Most active in past 12 months · UPWK ceo insider trading
Showing all insiders · Click a card to filter the transactions table below
▸ Aggregated from reportingName · top 5 by trade count (12M) · no extra API
Recent insider transactions
UPWK executive sell shares · UPWK board member insider trading · UPWK insider trading SEC filing
Scroll horizontally to see all columns
| Date | Insider | Type | Shares | Value | Filing |
|---|---|---|---|---|---|
| May 18, 2026 | Kappus Anthony Ray GM & Chief Operating Officer | Option | 5,114 | — | Form 4 |
| May 18, 2026 | Kappus Anthony Ray GM & Chief Operating Officer | Sale | 1,905 | $17K | Form 4 |
| May 18, 2026 | Gessert Erica CFO | Option | 8,524 | — | Form 4 |
| May 18, 2026 | Gessert Erica CFO | Option | 37,500 | — | Form 4 |
| May 18, 2026 | Gessert Erica CFO | Sale | 22,162 | $192K | Form 4 |
| May 18, 2026 | Brown Hayden President & CEO · Director | Option | 13,638 | — | Form 4 |
| May 18, 2026 | Brown Hayden President & CEO · Director | Option | 18,334 | — | Form 4 |
| May 18, 2026 | Brown Hayden President & CEO · Director | Sale | 22,546 | $195K | Form 4 |
| May 18, 2026 | Brown Hayden President & CEO · Director | Option | 14,850 | — | Form 4 |
| May 18, 2026 | Brown Hayden President & CEO · Director | Sale | 50,000 | $428K | Form 4 |
| Mar 18, 2026 | Mekhalfa Sabrina CAO | Option | 3,577 | — | Form 4 |
| Mar 18, 2026 | Mekhalfa Sabrina CAO | Sale | 1,482 | $18K | Form 4 |
| Mar 18, 2026 | Gessert Erica CFO | Option | 9,699 | — | Form 4 |
| Mar 18, 2026 | Gessert Erica CFO | Sale | 9,278 | $114K | Form 4 |
| Mar 18, 2026 | Gessert Erica CFO | Option | 8,433 | — | Form 4 |
| Mar 18, 2026 | Brown Hayden President & CEO · Director | Option | 28,677 | — | Form 4 |
| Mar 18, 2026 | Brown Hayden President & CEO · Director | Sale | 23,745 | $292K | Form 4 |
| Mar 18, 2026 | Brown Hayden President & CEO · Director | Option | 17,733 | — | Form 4 |
| Mar 18, 2026 | Bottoms Dave GM, Marketplace | Option | 5,904 | — | Form 4 |
| Mar 18, 2026 | Bottoms Dave GM, Marketplace | Option | 6,024 | — | Form 4 |
| Mar 18, 2026 | Bottoms Dave GM, Marketplace | Sale | 11,575 | $143K | Form 4 |
| Mar 18, 2026 | Bottoms Dave GM, Marketplace | Option | 8,980 | — | Form 4 |
| Mar 19, 2026 | Bottoms Dave GM, Marketplace | Sale | 7,000 | $80K | Form 4 |
| Feb 18, 2026 | Gessert Erica CFO | Option | 37,500 | — | Form 4 |
| Feb 18, 2026 | Gessert Erica CFO | Sale | 26,292 | $363K | Form 4 |
Kappus Anthony Ray
GM & Chief Operating Officer
Date
May 18
Shares
5,114
Price
—
Value
—
Kappus Anthony Ray
GM & Chief Operating Officer
Date
May 18
Shares
1,905
Price
$8.66
Value
$17K
Brown Hayden
President & CEO · Director
Date
May 18
Shares
13,638
Price
—
Value
—
Brown Hayden
President & CEO · Director
Date
May 18
Shares
18,334
Price
—
Value
—
Brown Hayden
President & CEO · Director
Date
May 18
Shares
22,546
Price
$8.66
Value
$195K
Brown Hayden
President & CEO · Director
Date
May 18
Shares
14,850
Price
—
Value
—
Brown Hayden
President & CEO · Director
Date
May 18
Shares
50,000
Price
$8.57
Value
$428K
Brown Hayden
President & CEO · Director
Date
Mar 18
Shares
28,677
Price
—
Value
—
Brown Hayden
President & CEO · Director
Date
Mar 18
Shares
23,745
Price
$12.31
Value
$292K
Brown Hayden
President & CEO · Director
Date
Mar 18
Shares
17,733
Price
—
Value
—
⚡ = value ≥ $1M · Award/Option price shows — · formType=4 · securityName=Common Stock · url → sec.gov/Archives/edgar
▸ Source: SEC EDGAR · Form 4 filings · ⚡ = value ≥ $1M · Award/Option price shows —
About UPWK insider trading
UPWK insider trades
Upwork Inc. (UPWK) insider trading data is sourced from SEC Form 4 filings submitted by corporate insiders, including Brown Hayden (President & CEO · Director), Bottoms Dave (GM, Marketplace), Gessert Erica (CFO). Over the past 12 months, 5 insiders have filed transactions with the SEC. UPWK insiders have been primarily selling, which may reflect pre-scheduled Rule 10b5-1 plan executions.
For Upwork Inc.'s institutional ownership breakdown and insider ownership percentage, see the Ownership tab → Ownership tab →
Frequently asked questions
UPWK insider trading · 5 questionsThe insiders of Upwork Inc. (UPWK) include executives and directors such as Brown Hayden (President & CEO · Director), Bottoms Dave (GM, Marketplace), Gessert Erica (CFO), among others. Over the past 12 months, 5 insiders have filed Form 4 transactions with the SEC. Insider transactions are required to be reported within 2 business days of the trade date.
▸ Source: FMP /stable/insider-trading/search · SEC EDGAR Form 3 & 4 · acquisitionOrDisposition A=Buy, D=Sell · RSU vesting (M-Exempt) excluded from sentiment bar · As of Jun 8, 2026