Upwork Inc. (UPWK) Insider Trading

Last 12 months

Insiders sold $15.8M and bought nothing on the open market.

26% of the selling was scheduled in advance under 10b5-1 plans. President & CEO Hayden Brown sold $6.83M on Nov 26, 2025, 33% of their stake, outside a plan. The last open-market buy by an executive or director was in May 2022.

Net open-market

−$15.8M

0 buys · 31 sales

Under a 10b5-1 plan

26%

of the value sold

Insiders who bought / sold

0 / 6

executives and directors

Last open-market buy

May 2022

May 12, 2022

Get an email when UPWK's executives or directors buy, or make a large sale outside a plan.

Trades · last 2 years

Date	Insider	Trade	Shares	Price	Value	Of their stake	Filing
Oct 19	Anthony Ray Kappus GM & Chief Operating Officer	SoldNo plan	559	$8.43	$5k	0.7%	Form 4
Sep 18	Erica Gessert Chief Financial Officer	SoldNo plan	9,336	$8.45	$79k	2.4%	Form 4
Sep 18	Sabrina Mekhalfa Chief Accounting Officer	SoldNo plan	1,299	$8.45	$11k	16%	Form 4
Sep 18	Anthony Ray Kappus GM & Chief Operating Officer	SoldNo plan	45,732	$8.45	$386k	37%	Form 4
Sep 18	Hayden Brown President & CEO	SoldNo plan	23,893	$8.45	$202k	2.9%	Form 4
Aug 18	Erica Gessert Chief Financial Officer	SoldNo plan	22,844	$8.43	$193k	5.9%	Form 4
Aug 18	Anthony Ray Kappus GM & Chief Operating Officer	SoldNo plan	1,964	$8.43	$17k	21%	Form 4
Aug 18	Hayden Brown President & CEO	Sold10b5-1 plan 2 parts	73,241	$8.43 average	$617k	8.7%	Form 4
Jul 18	Anthony Ray Kappus GM & Chief Operating Officer	SoldNo plan	558	$9.06	$5k	12%	Form 4
Jun 18	Erica Gessert Chief Financial Officer	SoldNo plan	9,169	$8.15	$75k	2.6%	Form 4
Jun 18	Sabrina Mekhalfa Chief Accounting Officer	SoldNo plan	1,276	$8.15	$10k	22%	Form 4
Jun 18	Hayden Brown President & CEO	SoldNo plan	23,468	$8.15	$191k	2.9%	Form 4
May 18	Erica Gessert Chief Financial Officer	SoldNo plan	22,162	$8.66	$192k	6.2%	Form 4
May 18	Anthony Ray Kappus GM & Chief Operating Officer	SoldNo plan	1,905	$8.66	$16k	37%	Form 4
May 18	Hayden Brown President & CEO	Sold10b5-1 plan 2 parts	72,546	$8.60 average	$624k	8.6%	Form 4
Mar 18 – 19	Dave Bottoms GM, Marketplace	Sold10b5-1 plan 2 parts	18,575	$12.00 average	$223k	87%	Form 4
Mar 18	Erica Gessert Chief Financial Officer	SoldNo plan	9,278	$12.31	$114k	2.9%	Form 4
Mar 18	Sabrina Mekhalfa Chief Accounting Officer	SoldNo plan	1,482	$12.31	$18k	41%	Form 4
Mar 18	Hayden Brown President & CEO	SoldNo plan	23,745	$12.31	$292k	2.9%	Form 4
Feb 18 – 19	Dave Bottoms GM, Marketplace	Sold10b5-1 plan 2 parts	32,662	$13.66 average	$446k	99%	Form 4
Feb 18	Erica Gessert Chief Financial Officer	SoldNo plan	26,292	$13.80	$363k	8.1%	Form 4
Feb 18	Hayden Brown President & CEO	Sold10b5-1 plan 2 parts	123,152	$13.80 average	$1.7M	14%	Form 4
Dec 18, 2025 – Dec 19, 2025	Dave Bottoms GM, Marketplace	Sold10b5-1 plan 2 parts	20,907	$20.62 average	$431k	98%	Form 4
Dec 18, 2025	Erica Gessert Chief Financial Officer	SoldNo plan	9,044	$20.59	$186k	3.5%	Form 4
Dec 18, 2025	Hayden Brown President & CEO	SoldNo plan	23,147	$20.59	$477k	3.1%	Form 4
Nov 25, 2025 – Nov 26, 2025	Hayden Brown President & CEO	SoldNo plan 3 parts	350,000	$19.51 average	$6.83M	33%	Form 4
Nov 21, 2025	Hayden Brown President & CEO	SoldNo plan	60,000	$18.20	$1.09M	5.4%	Form 4
Nov 21, 2025	Gary Steele Director	SoldNo plan	12,500	$17.51	$219k	13%	Form 4
Nov 17, 2025 – Nov 19, 2025	Dave Bottoms GM, Marketplace	Sold10b5-1 plan 4 parts	4,311	$17.25 average	$74k	93%	Form 4
Nov 18, 2025	Erica Gessert Chief Financial Officer	SoldNo plan 2 parts	18,493	$16.70 average	$309k	7.2%	Form 4
Nov 18, 2025	Hayden Brown President & CEO	SoldNo plan 2 parts	24,846	$16.70 average	$415k	2.2%	Form 4
Sep 18, 2025 – Sep 19, 2025	Dave Bottoms GM, Marketplace	Sold10b5-1 plan 2 parts	20,908	$19.54 average	$409k	98%	Form 4
Sep 17, 2025 – Sep 19, 2025	Hayden Brown President & CEO	Sold10b5-1 plan 4 parts	82,344	$19.04 average	$1.57M	7.1%	Form 4
Sep 18, 2025	Erica Gessert Chief Financial Officer	SoldNo plan	8,730	$19.16	$167k	3.8%	Form 4
Aug 29, 2025	Dave Bottoms GM, Marketplace	Sold10b5-1 plan	1,690	$14.95	$25k	83%	Form 4
Aug 19, 2025	Olivier Marie Chief Accounting Officer	Sold10b5-1 plan	1,686	$13.88	$23k	69%	Form 4
Aug 18, 2025	Erica Gessert Chief Financial Officer	SoldNo plan	19,036	$13.84	$263k	8.3%	Form 4
Aug 18, 2025	Dave Bottoms GM, Marketplace	SoldNo plan	2,060	$13.84	$29k	50%	Form 4
Aug 15, 2025 – Aug 18, 2025	Hayden Brown President & CEO	Sold10b5-1 plan 2 parts	85,577	$13.78 average	$1.18M	7.1%	Form 4
Aug 14, 2025 – Aug 18, 2025	Olivier Marie Chief Accounting Officer	Sold10b5-1 plan 2 parts	2,235	$13.93 average	$31k	48%	Form 4

Oct 19No plan
Anthony Ray Kappus
GM & Chief Operating Officer · sold 559 at $8.43
$5k
0.7% of stake
Sep 18No plan
Erica Gessert
Chief Financial Officer · sold 9,336 at $8.45
$79k
2.4% of stake
Sep 18No plan
Sabrina Mekhalfa
Chief Accounting Officer · sold 1,299 at $8.45
$11k
16% of stake
Sep 18No plan
Anthony Ray Kappus
GM & Chief Operating Officer · sold 45,732 at $8.45
$386k
37% of stake
Sep 18No plan
Hayden Brown
President & CEO · sold 23,893 at $8.45
$202k
2.9% of stake
Aug 18No plan
Erica Gessert
Chief Financial Officer · sold 22,844 at $8.43
$193k
5.9% of stake
Aug 18No plan
Anthony Ray Kappus
GM & Chief Operating Officer · sold 1,964 at $8.43
$17k
21% of stake
Aug 1810b5-1 plan
Hayden Brown
President & CEO · sold 73,241 at avg $8.43
$617k
8.7% of stake
Jul 18No plan
Anthony Ray Kappus
GM & Chief Operating Officer · sold 558 at $9.06
$5k
12% of stake
Jun 18No plan
Erica Gessert
Chief Financial Officer · sold 9,169 at $8.15
$75k
2.6% of stake
Jun 18No plan
Sabrina Mekhalfa
Chief Accounting Officer · sold 1,276 at $8.15
$10k
22% of stake
Jun 18No plan
Hayden Brown
President & CEO · sold 23,468 at $8.15
$191k
2.9% of stake
May 18No plan
Erica Gessert
Chief Financial Officer · sold 22,162 at $8.66
$192k
6.2% of stake
May 18No plan
Anthony Ray Kappus
GM & Chief Operating Officer · sold 1,905 at $8.66
$16k
37% of stake
May 1810b5-1 plan
Hayden Brown
President & CEO · sold 72,546 at avg $8.60
$624k
8.6% of stake
Mar 18 – 1910b5-1 plan
Dave Bottoms
GM, Marketplace · sold 18,575 at avg $12.00
$223k
87% of stake
Mar 18No plan
Erica Gessert
Chief Financial Officer · sold 9,278 at $12.31
$114k
2.9% of stake
Mar 18No plan
Sabrina Mekhalfa
Chief Accounting Officer · sold 1,482 at $12.31
$18k
41% of stake
Mar 18No plan
Hayden Brown
President & CEO · sold 23,745 at $12.31
$292k
2.9% of stake
Feb 18 – 1910b5-1 plan
Dave Bottoms
GM, Marketplace · sold 32,662 at avg $13.66
$446k
99% of stake
Feb 18No plan
Erica Gessert
Chief Financial Officer · sold 26,292 at $13.80
$363k
8.1% of stake
Feb 1810b5-1 plan
Hayden Brown
President & CEO · sold 123,152 at avg $13.80
$1.7M
14% of stake
Dec 18, 2025 – Dec 19, 202510b5-1 plan
Dave Bottoms
GM, Marketplace · sold 20,907 at avg $20.62
$431k
98% of stake
Dec 18, 2025No plan
Erica Gessert
Chief Financial Officer · sold 9,044 at $20.59
$186k
3.5% of stake
Dec 18, 2025No plan
Hayden Brown
President & CEO · sold 23,147 at $20.59
$477k
3.1% of stake
Nov 25, 2025 – Nov 26, 2025No plan
Hayden Brown
President & CEO · sold 350,000 at avg $19.51
$6.83M
33% of stake
Nov 21, 2025No plan
Hayden Brown
President & CEO · sold 60,000 at $18.20
$1.09M
5.4% of stake
Nov 21, 2025No plan
Gary Steele
Director · sold 12,500 at $17.51
$219k
13% of stake
Nov 17, 2025 – Nov 19, 202510b5-1 plan
Dave Bottoms
GM, Marketplace · sold 4,311 at avg $17.25
$74k
93% of stake
Nov 18, 2025No plan
Erica Gessert
Chief Financial Officer · sold 18,493 at avg $16.70
$309k
7.2% of stake
Nov 18, 2025No plan
Hayden Brown
President & CEO · sold 24,846 at avg $16.70
$415k
2.2% of stake
Sep 18, 2025 – Sep 19, 202510b5-1 plan
Dave Bottoms
GM, Marketplace · sold 20,908 at avg $19.54
$409k
98% of stake
Sep 17, 2025 – Sep 19, 202510b5-1 plan
Hayden Brown
President & CEO · sold 82,344 at avg $19.04
$1.57M
7.1% of stake
Sep 18, 2025No plan
Erica Gessert
Chief Financial Officer · sold 8,730 at $19.16
$167k
3.8% of stake
Aug 29, 202510b5-1 plan
Dave Bottoms
GM, Marketplace · sold 1,690 at $14.95
$25k
83% of stake
Aug 19, 202510b5-1 plan
Olivier Marie
Chief Accounting Officer · sold 1,686 at $13.88
$23k
69% of stake
Aug 18, 2025No plan
Erica Gessert
Chief Financial Officer · sold 19,036 at $13.84
$263k
8.3% of stake
Aug 18, 2025No plan
Dave Bottoms
GM, Marketplace · sold 2,060 at $13.84
$29k
50% of stake
Aug 15, 2025 – Aug 18, 202510b5-1 plan
Hayden Brown
President & CEO · sold 85,577 at avg $13.78
$1.18M
7.1% of stake
Aug 14, 2025 – Aug 18, 202510b5-1 plan
Olivier Marie
Chief Accounting Officer · sold 2,235 at avg $13.93
$31k
48% of stake

How to read this. Insiders sell for many reasons: taxes, diversifying, a house. Open-market buys are rarer and say more. A 10b5-1 plan is a trading schedule set up months in advance, so those sales were not timed on news. Large holders (funds and 10% owners) are listed under Everything but not counted as insiders. If you own or watch UPWK, we send a push when an executive buys or makes a large sale outside a plan.

Source: SEC Form 4 filings, filed within two business days of each trade and checked for new ones every hour.

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Data sourced from SEC EDGAR filings and third-party price providers. Scores, valuations, and metrics are algorithmic estimates. This is not investment advice. See our Terms and Methodology.

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