UPWORK, INC (UPWK) - Insider Trading & Ownership

Real time insider trading transaction history:

  • Insiders are prohibited from making short-swing profits by trading their shares within 6 months of the registration or acquiring the shares.
  • Shares are not adjusted for stock split.
"Insiders might sell their shares for any number of reasons, but they buy them for only one: they think the price will rise"
- Peter Lynch
What is insider trading>>
Time period
Insider Trading Transactions for UPWORK, INC
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Common stock purchase or sale:
Transaction
Date
Reported
DateTime
CompanySymbolInsider
Relationship
Shares
Traded
Average
Price
Total
Amount
Shares
Owned
Filing
2026-07-18
Sale
2026-07-21
4:40 pm
UPWORK INCUPWKKappus Anthony Ray
GM & Chief Operating Officer
558$9.0554$5,05325,254
(Direct)
View
2026-06-18
Sale
2026-06-23
5:18 pm
UPWORK INCUPWKGessert Erica
Chief Financial Officer
9,169$8.1507$74,734507,337
(Direct)
View
2026-06-18
Sale
2026-06-23
5:18 pm
UPWORK INCUPWKMekhalfa Sabrina
Chief Accounting Officer
1,276$8.1509$10,40140,171
(Direct)
View
2026-06-18
Sale
2026-06-23
5:16 pm
UPWORK INCUPWKBrown Hayden
President & CEO
23,468$8.1507$191,2811,237,080
(Direct)
View
2026-05-18
Sale
2026-05-20
4:16 pm
UPWORK INCUPWKKappus Anthony Ray
GM & Chief Operating Officer
1,905$8.6634$16,50479,928
(Direct)
View
2026-05-18
Sale
2026-05-20
4:16 pm
UPWORK INCUPWKGessert Erica
Chief Financial Officer
22,162$8.6634$191,998610,510
(Direct)
View
2026-05-18
Sale
2026-05-20
4:15 pm
UPWORK INCUPWKBrown Hayden
President & CEO
72,546$8.5987$623,8001,078,685
(Direct)
View
2026-03-18
Sale
2026-03-20
4:52 pm
UPWORK INCUPWKMekhalfa Sabrina
Chief Accounting Officer
1,482$12.31$18,24741,447
(Direct)
View
2026-03-18
Sale
2026-03-20
4:51 pm
UPWORK INCUPWKGessert Erica
Chief Financial Officer
9,278$12.31$114,231491,100
(Direct)
View
2026-03-18
Sale
2026-03-20
4:50 pm
UPWORK INCUPWKBrown Hayden
President & CEO
23,745$12.31$292,3441,284,728
(Direct)
View
2026-03-18
Sale
2026-03-20
4:49 pm
UPWORK INCUPWKBottoms Dave
GM, Marketplace
18,575$12$222,957139,676
(Direct)
View
2026-02-18
Sale
2026-02-19
8:03 pm
UPWORK INCUPWKGessert Erica
Chief Financial Officer
26,292$13.8$362,887622,274
(Direct)
View
2026-02-18
Sale
2026-02-19
8:02 pm
UPWORK INCUPWKBottoms Dave
GM, Marketplace
32,662$13.66$446,25597,178
(Direct)
View
2026-02-18
Sale
2026-02-19
8:02 pm
UPWORK INCUPWKBrown Hayden
President & CEO
123,152$13.8$1,698,9591,127,022
(Direct)
View
2025-12-18
Sale
2025-12-22
4:34 pm
UPWORK INCUPWKGessert Erica
Chief Financial Officer
9,044$20.59$186,187448,693
(Direct)
View
2025-12-18
Sale
2025-12-22
4:33 pm
UPWORK INCUPWKBrown Hayden
President & CEO
23,147$20.59$476,5501,253,564
(Direct)
View
2025-12-18
Sale
2025-12-22
4:33 pm
UPWORK INCUPWKBottoms Dave
GM, Marketplace
20,907$20.62$431,143158,251
(Direct)
View
2025-11-25
Sale
2025-11-28
3:32 pm
UPWORK INCUPWKBrown Hayden
President & CEO
350,000$19.51$6,827,478697,894
(Direct)
View
2025-11-21
Sale
2025-11-25
4:32 pm
UPWORK INCUPWKBrown Hayden
President & CEO
60,000$18.2$1,092,1141,047,894
(Direct)
View
2025-11-21
Sale
2025-11-25
4:31 pm
UPWORK INCUPWKSteele Gary
Director
12,500$17.51$218,84985,129
(Direct)
View
2025-11-18
Sale
2025-11-20
6:19 pm
UPWORK INCUPWKBrown Hayden
President & CEO
24,846$16.7$415,0081,291,011
(Direct)
View
2025-11-18
Sale
2025-11-20
6:18 pm
UPWORK INCUPWKGessert Erica
Chief Financial Officer
18,493$16.7$308,840462,612
(Direct)
View
2025-11-17
Sale
2025-11-19
7:18 pm
UPWORK INCUPWKBottoms Dave
GM, Marketplace
4,311$17.25$74,38419,095
(Direct)
View
2025-09-18
Sale
2025-09-22
4:34 pm
UPWORK INCUPWKGessert Erica
Chief Financial Officer
8,730$19.16$167,303438,730
(Direct)
View
2025-09-18
Sale
2025-09-22
4:33 pm
UPWORK INCUPWKBottoms Dave
GM, Marketplace
20,908$19.54$408,647179,158
(Direct)
View
2025-09-17
Sale
2025-09-19
5:55 pm
UPWORK INCUPWKBrown Hayden
President & CEO
82,344$19.04$1,568,1981,661,175
(Direct)
View
2025-08-29
Sale
2025-09-03
4:35 pm
UPWORK INCUPWKBottoms Dave
GM, Marketplace
1,690$14.95$25,266345
(Direct)
View

Stock options: Exercise, Award, Grant, Conversion
Transaction
Date
Reported
DateTime
Exercisable
Expiration
CompanySymnbolInsider
Relationship
Shares
Traded
Conversion
Price
Shares
Owned
Filing
2026-07-18
Exercise
2026-07-21
4:40 pm
N/A
N/A
UPWORK INCUPWKKappus Anthony Ray
GM & Chief Operating Officer
1,412$025,254
(Direct)
View
2026-06-18
Exercise
2026-06-23
5:18 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
18,132$0507,337
(Direct)
View
2026-06-18
Exercise
2026-06-23
5:18 pm
N/A
N/A
UPWORK INCUPWKMekhalfa Sabrina
Chief Accounting Officer
3,577$040,171
(Direct)
View
2026-06-18
Exercise
2026-06-23
5:16 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
46,411$01,237,080
(Direct)
View
2026-06-04
Option Award
2026-06-08
5:00 pm
N/A
N/A
UPWORK INCUPWKBRAMLEY CLAIRE
Director
45,146$045,146
(Direct)
View
2026-06-04
Option Award
2026-06-08
5:00 pm
N/A
N/A
UPWORK INCUPWKLISSY DAVID H
Director
66,026$066,026
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:58 pm
N/A
N/A
UPWORK INCUPWKLAYTON THOMAS
Director
33,859$01,691,430
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:58 pm
N/A
N/A
UPWORK INCUPWKKELMAN GLENN
Director
27,087$066,422
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:58 pm
N/A
N/A
UPWORK INCUPWKSteele Gary
Director
27,087$0112,216
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:57 pm
N/A
N/A
UPWORK INCUPWKEVAN DANA L
Director
20,880$056,835
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:57 pm
N/A
N/A
UPWORK INCUPWKHARVEY KEVIN
Director
27,087$02,712,523
(Direct)
View

Ownership
2026-06-08
4:57 pm
N/A
N/A
UPWORK INCUPWKBRAMLEY CLAIRE
Director
0$00
(Direct)
View

Ownership
2026-06-08
4:56 pm
N/A
N/A
UPWORK INCUPWKLISSY DAVID H
Director
0$00
(Direct)
View
2026-05-18
Exercise
2026-05-20
4:16 pm
N/A
N/A
UPWORK INCUPWKKappus Anthony Ray
GM & Chief Operating Officer
5,114$079,928
(Direct)
View
2026-05-18
Exercise
2026-05-20
4:16 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
46,024$0610,510
(Direct)
View
2026-05-18
Exercise
2026-05-20
4:15 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
46,822$01,078,685
(Direct)
View
2026-04-18
Option Award
2026-04-21
6:02 pm
N/A
N/A
UPWORK INCUPWKKappus Anthony Ray
GM & Chief Operating Officer
22,603$022,603
(Direct)
View

Ownership
2026-04-21
6:00 pm
N/A
N/A
UPWORK INCUPWKKappus Anthony Ray
GM & Chief Operating Officer
0$0541,275
(Direct)
View
2026-03-18
Exercise
2026-03-20
4:52 pm
N/A
N/A
UPWORK INCUPWKMekhalfa Sabrina
Chief Accounting Officer
3,577$041,447
(Direct)
View
2026-03-18
Exercise
2026-03-20
4:51 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
18,132$0491,100
(Direct)
View
2026-03-18
Exercise
2026-03-20
4:50 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
46,410$01,284,728
(Direct)
View
2026-03-18
Exercise
2026-03-20
4:49 pm
N/A
N/A
UPWORK INCUPWKBottoms Dave
GM, Marketplace
20,908$0139,676
(Direct)
View
2026-02-18
Option Award
2026-02-19
8:03 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
136,388$0622,274
(Direct)
View
2026-02-17
Exercise
2026-02-19
8:03 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
77,977$0622,274
(Direct)
View
2026-02-18
Option Award
2026-02-19
8:02 pm
N/A
N/A
UPWORK INCUPWKBottoms Dave
GM, Marketplace
81,833$097,178
(Direct)
View
2026-02-17
Exercise
2026-02-19
8:02 pm
N/A
N/A
UPWORK INCUPWKBottoms Dave
GM, Marketplace
32,662$097,178
(Direct)
View
2026-02-18
Option Award
2026-02-19
8:02 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
218,221$01,127,022
(Direct)
View
2026-02-17
Exercise
2026-02-19
8:02 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
178,061$01,127,022
(Direct)
View
2025-12-18
Option Award
2025-12-22
4:34 pm
N/A
N/A
UPWORK INCUPWKMekhalfa Sabrina
Chief Accounting Officer
42,929$042,929
(Direct)
View
2025-12-18
Exercise
2025-12-22
4:34 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
18,133$0448,693
(Direct)
View
2025-12-18
Exercise
2025-12-22
4:33 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
46,411$01,253,564
(Direct)
View
2025-12-18
Exercise
2025-12-22
4:33 pm
N/A
N/A
UPWORK INCUPWKBottoms Dave
GM, Marketplace
20,907$0158,251
(Direct)
View

Ownership
2025-12-22
4:32 pm
N/A
N/A
UPWORK INCUPWKMekhalfa Sabrina
Chief Accounting Officer
0$00
(Direct)
View
2025-11-18
Exercise
2025-11-20
6:19 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
50,382$01,291,011
(Direct)
View
2025-11-18
Exercise
2025-11-20
6:18 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
37,500$0462,612
(Direct)
View
2025-11-18
Exercise
2025-11-19
7:18 pm
N/A
N/A
UPWORK INCUPWKBottoms Dave
GM, Marketplace
3,750$019,095
(Direct)
View
2025-09-18
Exercise
2025-09-22
4:34 pm
N/A
N/A
UPWORK INCUPWKGessert Erica
Chief Financial Officer
18,133$0438,730
(Direct)
View
2025-09-18
Exercise
2025-09-22
4:33 pm
N/A
N/A
UPWORK INCUPWKBottoms Dave
GM, Marketplace
20,908$0179,158
(Direct)
View
2025-09-18
Exercise
2025-09-19
5:55 pm
N/A
N/A
UPWORK INCUPWKBrown Hayden
President & CEO
46,411$01,661,175
(Direct)
View
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