Upwork UPWK Insider Ownership

NASDAQ UPWK

$8.75 +0.23 (+2.70%)

At close: Oct 20, 2026 · 4:00 PM EDT

Insider Holdings by Owner

3.47Mn Shares

Insider Ownership Statistics

as of 30 Sep, 2026

Insider Ownership

5.24%

▲+0.083% pp QoQ

Shares Held by Insiders

6.54Mn

filed for Sep 2026

▲+1.61% QoQ

Shares Outstanding

124.80Mn

124,797,586 shares

Direct Holdings

1.98Mn

Indirect: 4.56Mn

Net Shares Traded (QoQ)

+103.49K

net buying in Sep 2026

Insiders Holding Shares

with Form 4 holdings on file

Shares Owned by Insiders

Shares held % of outstanding

Latest —

Average ownership —

Peak ownership —

Shares Purchased/Sold by Insiders

Bought Sold

Latest quarter —

Net over range —

Buying quarters —

Insider Ownership Summary

Updated Oct 10, 2026

Over the past 12 months, Upwork insiders sold $15.8 million of stock on the open market (1.07Mn shares) and made no open-market purchases.

Behind Upwork's open-market sales in the past 12 months were 6 insiders, and no insider bought.
Hayden Brown (President & CEO) was the top open-market seller of Upwork over the past 12 months, with $12.44 million sold (798.04K shares) and the latest sale on September 18, 2026.
The latest open-market trade on record is a sale of 45.73K shares for $386,472 by Anthony Ray Kappus (GM & Chief Operating Officer) on September 18, 2026.
Apart from open-market trades, UPWK insiders received 79K shares in stock awards and acquired 1Mn shares through option exercises and conversions in the past 12 months.
Business Quant data shows Upwork insiders holding 6.54Mn shares in total in their latest Form 4 filings, or 5.24% of the 124.8Mn shares outstanding; that total is up 1.61% from 6.44Mn shares at the end of Q2 2026.
Indirect holdings, through trusts, partnerships, family members and other entities, make up 69.74% (4.56Mn shares) of Upwork's insider total, with the other 30.26% (1.98Mn shares) held directly.
Holdings in Upwork stock are reported by 16 insiders, the officers, directors and 10% owners who have filed a Form 4 in the past two years.
Upwork's three biggest insider holders are Kevin Harvey (Director, 2.71Mn shares), Thomas Layton (Director, 1.69Mn shares) and Hayden Brown (President & CEO, 793.59K shares), based on their latest Form 4 filings.
Of the shares held by UPWK insiders, 41.47% belong to Kevin Harvey.
In the last 12 months, 39 Form 4 filings with transactions in UPWK stock came from 12 insiders.
The insider data for UPWK reflects Form 4 filings through September 22, 2026.

Form 4 Holdings

Insiders Holding UPWK

Insiders 19

Shares held 3.47Mn

Of outstanding 2.78%

#	Insider	Position	Direct	Indirect	Total	Share of Insiders	Last Filed
1	Gregory C. Gretsch	Director	243,044	761,201	1,004,245	28.9%	11 Jun, 2024
2	Hayden Brown	President Ceo	793,593	0	793,593	22.9%	22 Sep, 2026
3	Erica Gessert	Chief Financial Officer	373,586	0	373,586	10.8%	22 Sep, 2026
4	Elizabeth A Nelson	Director	0	356,712	356,712	10.3%	14 May, 2025
5	Kevin Harvey	Director	147,216	0	147,216	4.2%	08 Jun, 2026
6	Gary Steele	Director	112,216	0	112,216	3.2%	08 Jun, 2026
7	Jeff Mccombs	Chief Financial Officer	97,264	0	97,264	2.8%	22 Nov, 2022
8	Anilu Vazquez-Ubarri	Director	83,968	0	83,968	2.4%	09 Jun, 2025
9	Leela Srinivasan	Director	79,469	0	79,469	2.3%	09 Jun, 2025
10	Anthony Ray Kappus	Gm Chief Operating Officer	76,342	0	76,342	2.2%	22 Sep, 2026
11	Glenn Kelman	Director	66,422	0	66,422	1.9%	08 Jun, 2026
12	David H Lissy	Director	66,026	0	66,026	1.9%	08 Jun, 2026
13	Dana L Evan	Director	56,835	0	56,835	1.6%	08 Jun, 2026
14	Thomas Layton	Director	52,296	0	52,296	1.5%	08 Jun, 2026
15	Eric Gilpin	Chief Sales Officer	51,188	0	51,188	1.5%	22 Feb, 2023
16	Claire Bramley	Director	45,146	0	45,146	1.3%	08 Jun, 2026
17	Sabrina Mekhalfa	Chief Accounting Officer	6,675	0	6,675	0.2%	22 Sep, 2026
18	Dave Bottoms	Gm, Marketplace	2,678	0	2,678	0.1%	20 Mar, 2026
19	Olivier Marie	Chief Accounting Officer	748	0	748	0.0%	21 Aug, 2025

Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.

Form 4 Filings

1,434 Insider Transactions

Source SEC Form 4

Latest quarter Sep 2026

Date	Insider	Position	Transaction	Shares	Price	Value	Shares Held After	Ownership
18 Sep, 2026	Erica Gessert	Chief Financial Officer	Acquired M	8,433	—	—	373,222	Direct
18 Sep, 2026	Sabrina Mekhalfa	Chief Accounting Officer	Acquired M	3,578	—	—	7,974	Direct
18 Sep, 2026	Hayden Brown	President Ceo	Acquired M	17,733	—	—	788,809	Direct
18 Sep, 2026	Anthony Ray Kappus	Gm Chief Operating Officer	Acquired M	114,860	—	—	122,074	Direct
18 Sep, 2026	Sabrina Mekhalfa	Chief Accounting Officer	Disposed S	1,299	$8.45	$10.98K	6,675	Direct
18 Sep, 2026	Hayden Brown	President Ceo	Acquired M	28,677	—	—	817,486	Direct
18 Sep, 2026	Erica Gessert	Chief Financial Officer	Acquired M	9,700	—	—	382,922	Direct
18 Sep, 2026	Anthony Ray Kappus	Gm Chief Operating Officer	Disposed S	45,732	$8.45	$386.47K	76,342	Direct
18 Sep, 2026	Erica Gessert	Chief Financial Officer	Disposed S	9,336	$8.45	$78.90K	373,586	Direct
18 Sep, 2026	Sabrina Mekhalfa	Chief Accounting Officer	Disposed M	3,578	$0.00	$0	32,197	Direct
18 Sep, 2026	Hayden Brown	President Ceo	Disposed S	23,893	$8.45	$201.92K	793,593	Direct
18 Sep, 2026	Anthony Ray Kappus	Gm Chief Operating Officer	Disposed M	114,860	$0.00	$0	344,582	Direct
18 Sep, 2026	Hayden Brown	President Ceo	Disposed M	17,733	$0.00	$0	106,400	Direct
18 Sep, 2026	Erica Gessert	Chief Financial Officer	Disposed M	8,433	$0.00	$0	50,598	Direct
18 Sep, 2026	Hayden Brown	President Ceo	Disposed M	28,677	$0.00	$0	286,775	Direct
18 Sep, 2026	Erica Gessert	Chief Financial Officer	Disposed M	9,700	$0.00	$0	96,997	Direct
18 Aug, 2026	Anthony Ray Kappus	Gm Chief Operating Officer	Acquired M	5,115	—	—	9,178	Direct
18 Aug, 2026	Hayden Brown	President Ceo	Acquired M	14,850	—	—	812,345	Direct
18 Aug, 2026	Erica Gessert	Chief Financial Officer	Acquired M	37,500	—	—	379,109	Direct
18 Aug, 2026	Anthony Ray Kappus	Gm Chief Operating Officer	Disposed S	1,964	$8.43	$16.55K	7,214	Direct

Showing 1 to 20 of 1,434 transactions