Upwork Inc (UPWK)

Upwork Inc. executives executed eight insider trading transactions over the past ninety days, totaling approximately 1.63 million dollars in sales. Key leadership, including the CEO and CFO, offloaded shares following the most recent earnings report. These divestments occurred amidst an 8.6% stock price increase, reflecting ongoing equity liquidation by management.
Ticker: UPWK Exchange: NSM


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Insider trades have triggered activity signals for Upwork Inc. Upgrade to see score, net flow, insiders and the full signal context.

Top insiders
Trades
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
214.19
Quantity 2,915
Value US$4,855,463
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
227.85
Quantity 96,363
Value US$3,389,169
2.2
ANTHONY KAPPUS Officer Officer
Transaction date
Proposed sale
Price
46.59
Quantity 42,100
Value US$317,294
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Planned sale
Price
8.43
Quantity 50,000 -6.1%
Value US$421,355
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
8.43
Quantity 23,241 -2.8%
Value US$195,822
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
8.43
Quantity 22,844 -5.9%
Value US$192,477
2.2
Kappus Anthony Ray GM & Chief Operating Officer Officer
Transaction date
Sale
Price
8.43
Quantity 1,964 -21.4%
Value US$16,548
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
8.43
Quantity 23,241
Value US$195,822
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
8.43
Quantity 22,844
Value US$192,477
3.6
HAYDEN BROWN Director; Officer Executive Director
Transaction date
Proposed sale
Price
8.19
Quantity 50,000
Value US$409,500
2.2
Kappus Anthony Ray GM & Chief Operating Officer Officer
Transaction date
Sale
Price
9.06
Quantity 558 -12.1%
Value US$5,053
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
8.15
Quantity 9,169 -2.6%
Value US$74,734
2.8
Mekhalfa Sabrina Chief Accounting Officer Officer
Transaction date
Sale
Price
8.15
Quantity 1,276 -22.5%
Value US$10,401
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
8.15
Quantity 23,468 -2.9%
Value US$191,281
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
8.15
Quantity 23,468
Value US$191,281
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
8.15
Quantity 9,169
Value US$74,734
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
8.66
Quantity 22,162 -6.2%
Value US$191,998
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Planned sale
Price
8.57
Quantity 50,000 -6.1%
Value US$428,475
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
8.66
Quantity 22,546 -2.7%
Value US$195,325
2.2
Kappus Anthony Ray GM & Chief Operating Officer Officer
Transaction date
Sale
Price
8.66
Quantity 1,905 -37.3%
Value US$16,504
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
8.66
Quantity 22,162
Value US$191,998
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
8.66
Quantity 22,546
Value US$195,325
3.6
HAYDEN BROWN Director; Officer Executive Director
Transaction date
Proposed sale
Price
8.17
Quantity 50,000
Value US$408,500
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Planned sale
Price
11.49
Quantity 7,000 -72.3%
Value US$80,448
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
12.09
Quantity 7,000
Value US$84,630
2.8
Mekhalfa Sabrina Chief Accounting Officer Officer
Transaction date
Sale
Price
12.31
Quantity 1,482 -41.4%
Value US$18,247
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
12.31
Quantity 9,278 -2.9%
Value US$114,231
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Sale
Price
12.31
Quantity 11,575 -54.5%
Value US$142,509
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
12.31
Quantity 23,745 -2.9%
Value US$292,344
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
12.31
Quantity 11,575
Value US$142,509
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
12.31
Quantity 9,278
Value US$114,229
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
12.31
Quantity 23,745
Value US$292,344
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Planned sale
Price
13.51
Quantity 15,649 -97.8%
Value US$211,441
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
13.73
Quantity 15,649
Value US$214,861
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
13.80
Quantity 26,292 -8.1%
Value US$362,887
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Sale
Price
13.80
Quantity 17,013 -51.5%
Value US$234,813
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Planned sale
Price
13.79
Quantity 50,000 -6.1%
Value US$689,300
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
13.80
Quantity 73,152 -8.1%
Value US$1,009,659
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
13.86
Quantity 73,152
Value US$1,014,012
3.6
HAYDEN LARSON BROWN Director; Officer Executive Director
Transaction date
Proposed sale
Price
12.76
Quantity 50,000
Value US$638,000
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
13.82
Quantity 26,292
Value US$363,377
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
13.90
Quantity 17,013
Value US$236,423
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Planned sale
Price
20.66
Quantity 9,622 -96.5%
Value US$198,808
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
20.47
Quantity 9,622
Value US$196,962
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
20.59
Quantity 23,147 -3.1%
Value US$476,550
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
20.59
Quantity 9,044 -3.5%
Value US$186,187
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Sale
Price
20.59
Quantity 11,285 -53.1%
Value US$232,336
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
20.59
Quantity 9,044
Value US$186,197
3.6
DAVID T. BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
20.59
Quantity 11,285
Value US$232,334
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
20.59
Quantity 23,147
Value US$476,548
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
19.44
Quantity 100,000 -12.5%
Value US$1,943,980
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
19.43
Quantity 175,000 -18.0%
Value US$3,400,162
3.6
HAYDEN LARSON BROWN Officer Officer
Transaction date
Proposed sale
Price
19.43
Quantity 275,000
Value US$5,344,528
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
19.78
Quantity 75,000 -7.2%
Value US$1,483,335
3.6
HAYDEN LARSON BROWN Officer Officer
Transaction date
Proposed sale
Price
19.78
Quantity 75,000
Value US$1,483,335
2.4
Steele Gary Non-Executive Director
Transaction date
Sale
Price
17.51
Quantity 12,500 -12.8%
Value US$218,849
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
18.20
Quantity 60,000 -5.4%
Value US$1,092,114
2.4
GARY STEELE Officer Officer
Transaction date
Proposed sale
Price
17.51
Quantity 12,500
Value US$218,849
3.6
HAYDEN LARSON BROWN Officer Officer
Transaction date
Proposed sale
Price
18.20
Quantity 60,000
Value US$1,092,114
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
17.08
Quantity 1,748
Value US$29,856
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Planned sale
Price
18.13
Quantity 1,748 -83.5%
Value US$31,690
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
17.24
Quantity 12,732 -1.1%
Value US$219,506
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
16.14
Quantity 12,114 -1.1%
Value US$195,502
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
17.24
Quantity 9,434 -3.8%
Value US$162,644
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
16.14
Quantity 9,059 -3.5%
Value US$146,196
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Sale
Price
17.24
Quantity 1,047 -33.3%
Value US$18,050
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Sale
Price
16.14
Quantity 955 -23.3%
Value US$15,416
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
16.70
Quantity 18,493
Value US$308,865
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
16.70
Quantity 2,002
Value US$33,437
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
16.70
Quantity 24,846
Value US$414,970
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Planned sale
Price
16.45
Quantity 561 -61.9%
Value US$9,228
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
16.48
Quantity 561
Value US$9,245
3.6
Bottoms Dave GM, Marketplace Officer
Transaction date
Planned sale
Price
19.96
Quantity 10,014 -96.7%
Value US$199,867
3.6
DAVID BOTTOMS Officer Officer
Transaction date
Proposed sale
Price
19.60
Quantity 10,014
Value US$196,274
3.6
HAYDEN L BROWN Director; Officer Executive Director
Transaction date
Proposed sale
Price
19.60
Quantity 20,000
Value US$392,000
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value
Number of shares Price Value Details
2026-09-18 2026-09-18 PrS Proposed sale

Officer

Officer
2,915
214.19
US$4,855,463
2,915 214.19 US$4,855,463
2026-09-18 2026-09-18 PrS Proposed sale

Officer; Director

Executive Director
96,363
227.85
US$3,389,169
96,363 227.85 US$3,389,169
2026-09-18 2026-09-18 PrS Proposed sale

Officer

Officer
42,100
46.59
US$317,294
42,100 46.59 US$317,294
2026-08-20 2026-08-18 PlS Planned sale

President & CEO

Executive Director
50,000 -6.1%
8.43
US$421,355
50,000 -6.1% 8.43 US$421,355
2026-08-20 2026-08-18 S Sale

President & CEO

Executive Director
23,241 -2.8%
8.43
US$195,822
23,241 -2.8% 8.43 US$195,822
2026-08-20 2026-08-18 S Sale

Chief Financial Officer

Officer
22,844 -5.9%
8.43
US$192,477
22,844 -5.9% 8.43 US$192,477
2026-08-20 2026-08-18 S Sale

GM & Chief Operating Officer

Officer
1,964 -21.4%
8.43
US$16,548
1,964 -21.4% 8.43 US$16,548
2026-08-18 2026-08-18 PrS Proposed sale

Officer; Director

Executive Director
23,241
8.43
US$195,822
23,241 8.43 US$195,822
2026-08-18 2026-08-18 PrS Proposed sale

Officer

Officer
22,844
8.43
US$192,477
22,844 8.43 US$192,477
2026-08-18 2026-08-18 PrS Proposed sale

Director; Officer

Executive Director
50,000
8.19
US$409,500
50,000 8.19 US$409,500
2026-07-21 2026-07-18 S Sale

GM & Chief Operating Officer

Officer
558 -12.1%
9.06
US$5,053
558 -12.1% 9.06 US$5,053
2026-06-23 2026-06-18 S Sale

Chief Financial Officer

Officer
9,169 -2.6%
8.15
US$74,734
9,169 -2.6% 8.15 US$74,734
2026-06-23 2026-06-18 S Sale

Chief Accounting Officer

Officer
1,276 -22.5%
8.15
US$10,401
1,276 -22.5% 8.15 US$10,401
2026-06-23 2026-06-18 S Sale

President & CEO

Executive Director
23,468 -2.9%
8.15
US$191,281
23,468 -2.9% 8.15 US$191,281
2026-06-18 2026-06-18 PrS Proposed sale

Officer; Director

Executive Director
23,468
8.15
US$191,281
23,468 8.15 US$191,281
2026-06-18 2026-06-18 PrS Proposed sale

Officer

Officer
9,169
8.15
US$74,734
9,169 8.15 US$74,734
2026-05-20 2026-05-18 S Sale

Chief Financial Officer

Officer
22,162 -6.2%
8.66
US$191,998
22,162 -6.2% 8.66 US$191,998
2026-05-20 2026-05-18 PlS Planned sale

President & CEO

Executive Director
50,000 -6.1%
8.57
US$428,475
50,000 -6.1% 8.57 US$428,475
2026-05-20 2026-05-18 S Sale

President & CEO

Executive Director
22,546 -2.7%
8.66
US$195,325
22,546 -2.7% 8.66 US$195,325
2026-05-20 2026-05-18 S Sale

GM & Chief Operating Officer

Officer
1,905 -37.3%
8.66
US$16,504
1,905 -37.3% 8.66 US$16,504
2026-05-18 2026-05-18 PrS Proposed sale

Officer

Officer
22,162
8.66
US$191,998
22,162 8.66 US$191,998
2026-05-18 2026-05-18 PrS Proposed sale

Officer; Director

Executive Director
22,546
8.66
US$195,325
22,546 8.66 US$195,325
2026-05-18 2026-05-18 PrS Proposed sale

Director; Officer

Executive Director
50,000
8.17
US$408,500
50,000 8.17 US$408,500
2026-03-20 2026-03-19 PlS Planned sale

GM, Marketplace

Officer
7,000 -72.3%
11.49
US$80,448
7,000 -72.3% 11.49 US$80,448
2026-03-19 2026-03-19 PrS Proposed sale

Officer

Officer
7,000
12.09
US$84,630
7,000 12.09 US$84,630
2026-03-20 2026-03-18 S Sale

Chief Accounting Officer

Officer
1,482 -41.4%
12.31
US$18,247
1,482 -41.4% 12.31 US$18,247
2026-03-20 2026-03-18 S Sale

Chief Financial Officer

Officer
9,278 -2.9%
12.31
US$114,231
9,278 -2.9% 12.31 US$114,231
2026-03-20 2026-03-18 S Sale

GM, Marketplace

Officer
11,575 -54.5%
12.31
US$142,509
11,575 -54.5% 12.31 US$142,509
2026-03-20 2026-03-18 S Sale

President & CEO

Executive Director
23,745 -2.9%
12.31
US$292,344
23,745 -2.9% 12.31 US$292,344
2026-03-18 2026-03-18 PrS Proposed sale

Officer

Officer
11,575
12.31
US$142,509
11,575 12.31 US$142,509
2026-03-18 2026-03-18 PrS Proposed sale

Officer

Officer
9,278
12.31
US$114,229
9,278 12.31 US$114,229
2026-03-18 2026-03-18 PrS Proposed sale

Officer; Director

Executive Director
23,745
12.31
US$292,344
23,745 12.31 US$292,344
2026-02-19 2026-02-19 PlS Planned sale

GM, Marketplace

Officer
15,649 -97.8%
13.51
US$211,441
15,649 -97.8% 13.51 US$211,441
2026-02-19 2026-02-19 PrS Proposed sale

Officer

Officer
15,649
13.73
US$214,861
15,649 13.73 US$214,861
2026-02-19 2026-02-18 S Sale

Chief Financial Officer

Officer
26,292 -8.1%
13.80
US$362,887
26,292 -8.1% 13.80 US$362,887
2026-02-19 2026-02-18 S Sale

GM, Marketplace

Officer
17,013 -51.5%
13.80
US$234,813
17,013 -51.5% 13.80 US$234,813
2026-02-19 2026-02-18 PlS Planned sale

President & CEO

Executive Director
50,000 -6.1%
13.79
US$689,300
50,000 -6.1% 13.79 US$689,300
2026-02-19 2026-02-18 S Sale

President & CEO

Executive Director
73,152 -8.1%
13.80
US$1,009,659
73,152 -8.1% 13.80 US$1,009,659
2026-02-18 2026-02-18 PrS Proposed sale

Officer; Director

Executive Director
73,152
13.86
US$1,014,012
73,152 13.86 US$1,014,012
2026-02-18 2026-02-18 PrS Proposed sale

Director; Officer

Executive Director
50,000
12.76
US$638,000
50,000 12.76 US$638,000
2026-02-18 2026-02-18 PrS Proposed sale

Officer

Officer
26,292
13.82
US$363,377
26,292 13.82 US$363,377
2026-02-18 2026-02-18 PrS Proposed sale

Officer

Officer
17,013
13.90
US$236,423
17,013 13.90 US$236,423
2025-12-22 2025-12-19 PlS Planned sale

GM, Marketplace

Officer
9,622 -96.5%
20.66
US$198,808
9,622 -96.5% 20.66 US$198,808
2025-12-19 2025-12-19 PrS Proposed sale

Officer

Officer
9,622
20.47
US$196,962
9,622 20.47 US$196,962
2025-12-22 2025-12-18 S Sale

President & CEO

Executive Director
23,147 -3.1%
20.59
US$476,550
23,147 -3.1% 20.59 US$476,550
2025-12-22 2025-12-18 S Sale

Chief Financial Officer

Officer
9,044 -3.5%
20.59
US$186,187
9,044 -3.5% 20.59 US$186,187
2025-12-22 2025-12-18 S Sale

GM, Marketplace

Officer
11,285 -53.1%
20.59
US$232,336
11,285 -53.1% 20.59 US$232,336
2025-12-18 2025-12-18 PrS Proposed sale

Officer

Officer
9,044
20.59
US$186,197
9,044 20.59 US$186,197
2025-12-18 2025-12-18 PrS Proposed sale

Officer

Officer
11,285
20.59
US$232,334
11,285 20.59 US$232,334
2025-12-18 2025-12-18 PrS Proposed sale

Officer; Director

Executive Director
23,147
20.59
US$476,548
23,147 20.59 US$476,548
2025-11-28 2025-11-26 S Sale

President & CEO

Executive Director
100,000 -12.5%
19.44
US$1,943,980
100,000 -12.5% 19.44 US$1,943,980
2025-11-28 2025-11-26 S Sale

President & CEO

Executive Director
175,000 -18.0%
19.43
US$3,400,162
175,000 -18.0% 19.43 US$3,400,162
2025-11-26 2025-11-26 PrS Proposed sale

Officer

Officer
275,000
19.43
US$5,344,528
275,000 19.43 US$5,344,528
2025-11-28 2025-11-25 S Sale

President & CEO

Executive Director
75,000 -7.2%
19.78
US$1,483,335
75,000 -7.2% 19.78 US$1,483,335
2025-11-25 2025-11-25 PrS Proposed sale

Officer

Officer
75,000
19.78
US$1,483,335
75,000 19.78 US$1,483,335
2025-11-25 2025-11-21 S Sale Non-Executive Director
12,500 -12.8%
17.51
US$218,849
12,500 -12.8% 17.51 US$218,849
2025-11-25 2025-11-21 S Sale

President & CEO

Executive Director
60,000 -5.4%
18.20
US$1,092,114
60,000 -5.4% 18.20 US$1,092,114
2025-11-21 2025-11-21 PrS Proposed sale

Officer

Officer
12,500
17.51
US$218,849
12,500 17.51 US$218,849
2025-11-21 2025-11-21 PrS Proposed sale

Officer

Officer
60,000
18.20
US$1,092,114
60,000 18.20 US$1,092,114
2025-11-19 2025-11-19 PrS Proposed sale

Officer

Officer
1,748
17.08
US$29,856
1,748 17.08 US$29,856
2025-11-19 2025-11-19 PlS Planned sale

GM, Marketplace

Officer
1,748 -83.5%
18.13
US$31,690
1,748 -83.5% 18.13 US$31,690
2025-11-20 2025-11-18 S Sale

President & CEO

Executive Director
12,732 -1.1%
17.24
US$219,506
12,732 -1.1% 17.24 US$219,506
2025-11-20 2025-11-18 S Sale

President & CEO

Executive Director
12,114 -1.1%
16.14
US$195,502
12,114 -1.1% 16.14 US$195,502
2025-11-20 2025-11-18 S Sale

Chief Financial Officer

Officer
9,434 -3.8%
17.24
US$162,644
9,434 -3.8% 17.24 US$162,644
2025-11-20 2025-11-18 S Sale

Chief Financial Officer

Officer
9,059 -3.5%
16.14
US$146,196
9,059 -3.5% 16.14 US$146,196
2025-11-19 2025-11-18 S Sale

GM, Marketplace

Officer
1,047 -33.3%
17.24
US$18,050
1,047 -33.3% 17.24 US$18,050
2025-11-19 2025-11-18 S Sale

GM, Marketplace

Officer
955 -23.3%
16.14
US$15,416
955 -23.3% 16.14 US$15,416
2025-11-18 2025-11-18 PrS Proposed sale

Officer

Officer
18,493
16.70
US$308,865
18,493 16.70 US$308,865
2025-11-18 2025-11-18 PrS Proposed sale

Officer

Officer
2,002
16.70
US$33,437
2,002 16.70 US$33,437
2025-11-18 2025-11-18 PrS Proposed sale

Officer; Director

Executive Director
24,846
16.70
US$414,970
24,846 16.70 US$414,970
2025-11-19 2025-11-17 PlS Planned sale

GM, Marketplace

Officer
561 -61.9%
16.45
US$9,228
561 -61.9% 16.45 US$9,228
2025-11-17 2025-11-17 PrS Proposed sale

Officer

Officer
561
16.48
US$9,245
561 16.48 US$9,245
2025-09-22 2025-09-19 PlS Planned sale

GM, Marketplace

Officer
10,014 -96.7%
19.96
US$199,867
10,014 -96.7% 19.96 US$199,867
2025-09-19 2025-09-19 PrS Proposed sale

Officer

Officer
10,014
19.60
US$196,274
10,014 19.60 US$196,274
2025-09-19 2025-09-19 PrS Proposed sale

Director; Officer

Executive Director
20,000
19.60
US$392,000
20,000 19.60 US$392,000