Upwork Inc. (UPWK)

Ticker: UPWK Exchange: NSM


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• Purchase • Sale • Planned purchase • Planned sale Net purchase Net sale Buy signal Sell signal Earnings
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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
1.9
Kappus Anthony Ray GM & Chief Operating Officer Officer
Transaction date
Sale
Price
287.75
Quantity 42,640 +29.6%
Value US$793,044
1.9
ANTHONY KAPPUS Officer Officer
Transaction date
Proposed sale
Price
111.90
Quantity 6,625
Value US$3,738,150
1.9
Kappus Anthony Ray GM & Chief Operating Officer Officer
Transaction date
Sale
Price
39.29
Quantity 80,207 +19.1%
Value US$2,685,761
3.6
Gessert Erica Chief Financial Officer Officer
Transaction date
Sale
Price
8.45
Quantity 9,336 -2.4%
Value US$78,897
2.8
Mekhalfa Sabrina Chief Accounting Officer Officer
Transaction date
Sale
Price
8.45
Quantity 1,299 -16.3%
Value US$10,978
3.6
Brown Hayden President & CEO Executive Director
Transaction date
Sale
Price
8.45
Quantity 23,893 -2.9%
Value US$201,917
3.6
ERICA GESSERT Officer Officer
Transaction date
Proposed sale
Price
8.45
Quantity 9,336
Value US$78,898
3.6
HAYDEN BROWN Officer; Director Executive Director
Transaction date
Proposed sale
Price
8.45
Quantity 23,893
Value US$201,917
1.9
ANTHONY KAPPUS Officer Officer
Transaction date
Proposed sale
Price
8.45
Quantity 45,732
Value US$386,477
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
1.9
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
1.9
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
1.9
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
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value
Number of shares Price Value Details
2026-10-20 2026-10-19 S Sale

GM & Chief Operating Officer

Officer
42,640 +29.6%
287.75
US$793,044
42,640 +29.6% 287.75 US$793,044
2026-10-19 2026-10-19 PrS Proposed sale

Officer

Officer
6,625
111.90
US$3,738,150
6,625 111.90 US$3,738,150
2026-09-22 2026-09-18 S Sale

GM & Chief Operating Officer

Officer
80,207 +19.1%
39.29
US$2,685,761
80,207 +19.1% 39.29 US$2,685,761
2026-09-22 2026-09-18 S Sale

Chief Financial Officer

Officer
9,336 -2.4%
8.45
US$78,897
9,336 -2.4% 8.45 US$78,897
2026-09-22 2026-09-18 S Sale

Chief Accounting Officer

Officer
1,299 -16.3%
8.45
US$10,978
1,299 -16.3% 8.45 US$10,978
2026-09-22 2026-09-18 S Sale

President & CEO

Executive Director
23,893 -2.9%
8.45
US$201,917
23,893 -2.9% 8.45 US$201,917
2026-09-18 2026-09-18 PrS Proposed sale

Officer

Officer
9,336
8.45
US$78,898
9,336 8.45 US$78,898
2026-09-18 2026-09-18 PrS Proposed sale

Officer; Director

Executive Director
23,893
8.45
US$201,917
23,893 8.45 US$201,917
2026-09-18 2026-09-18 PrS Proposed sale

Officer

Officer
45,732
8.45
US$386,477
45,732 8.45 US$386,477
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

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