United States Professional & Commercial Services

Upwork Inc (UPWK)

Track

Over the past 90 days, Upwork Inc. insiders have executed 13 transactions, all of which were sales, totaling approximately $685,295 in net value. Key executives, including the CEO and CFO, have consistently sold shares. These transactions occurred following the company's May 2026 earnings report, amid a 11.2% decline in stock price over the same period.
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.

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Top insiders
Trades
Sale 18 Jul 2026
Value US$1,525,521.89 | Price 156.81 | Shares 42,910 (+38.7%)
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value 		Number of shares Price Value Details
2026-07-21 2026-07-18 S Sale
1.6
Kappus Anthony Ray

GM & Chief Operating Officer

Officer
42,910 +38.7%
156.81
US$1,525,522 		42,910 +38.7% 156.81 US$1,525,522
2026-06-23 2026-06-18 S Sale
3.6
Gessert Erica

Chief Financial Officer

Officer
27,593 -21.2%
252.15
US$4,870,102 		27,593 -21.2% 252.15 US$4,870,102
2026-06-23 2026-06-18 S Sale
2.9
Mekhalfa Sabrina

Chief Accounting Officer

Officer
46,296 +29.0%
432.86
US$409,773 		46,296 +29.0% 432.86 US$409,773
2026-06-23 2026-06-18 S Sale
3.6
Brown Hayden

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
3.6
HAYDEN BROWN

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
3.6
ERICA GESSERT

Officer

Officer
9,169
8.15
US$74,734 		9,169 8.15 US$74,734
2026-05-20 2026-05-18 S Sale
3.6
Gessert Erica

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
3.6
Brown Hayden

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
3.6
Brown Hayden

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
1.6
Kappus Anthony Ray

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
3.6
ERICA GESSERT

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
3.6
HAYDEN BROWN

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
3.6
HAYDEN BROWN

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
3.6
Bottoms Dave

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
3.6
DAVID BOTTOMS

Officer

Officer
7,000
12.09
US$84,630 		7,000 12.09 US$84,630
2026-03-20 2026-03-18 S Sale
2.9
Mekhalfa Sabrina

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
3.6
Gessert Erica

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
3.6
Bottoms Dave

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
3.6
Brown Hayden

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
3.6
DAVID BOTTOMS

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
3.6
ERICA GESSERT

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
3.6
HAYDEN BROWN

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
3.6
Bottoms Dave

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
3.6
DAVID BOTTOMS

Officer

Officer
15,649
13.73
US$214,861 		15,649 13.73 US$214,861
2026-02-19 2026-02-18 S Sale
3.6
Gessert Erica

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
3.6
Bottoms Dave

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
3.6
Brown Hayden

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
3.6
Brown Hayden

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
3.6
HAYDEN BROWN

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
3.6
HAYDEN LARSON BROWN

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
3.6
ERICA GESSERT

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
3.6
DAVID BOTTOMS

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
3.6
Bottoms Dave

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
3.6
DAVID BOTTOMS

Officer

Officer
9,622
20.47
US$196,962 		9,622 20.47 US$196,962
2025-12-22 2025-12-18 S Sale
3.6
Brown Hayden

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
3.6
Gessert Erica

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
3.6
Bottoms Dave

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
3.6
ERICA GESSERT

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
3.6
DAVID T. BOTTOMS

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
3.6
HAYDEN BROWN

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
3.6
Brown Hayden

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
3.6
Brown Hayden

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
3.6
HAYDEN LARSON BROWN

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
3.6
Brown Hayden

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
3.6
HAYDEN LARSON BROWN

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
2.4
Steele Gary
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
3.6
Brown Hayden

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
2.4
GARY STEELE

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
3.6
HAYDEN LARSON BROWN

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
3.6
DAVID BOTTOMS

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
3.6
Bottoms Dave

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
3.6
Brown Hayden

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
3.6
Brown Hayden

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
3.6
Gessert Erica

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
3.6
Gessert Erica

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
3.6
Bottoms Dave

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
3.6
Bottoms Dave

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
3.6
ERICA GESSERT

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
3.6
DAVID BOTTOMS

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
3.6
HAYDEN BROWN

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
3.6
Bottoms Dave

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
3.6
DAVID BOTTOMS

Officer

Officer
561
16.48
US$9,245 		561 16.48 US$9,245
2025-09-22 2025-09-19 PlS Planned sale
3.6
Bottoms Dave

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
3.6
DAVID BOTTOMS

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
3.6
HAYDEN L BROWN

Director; Officer

Executive Director
20,000
19.60
US$392,000 		20,000 19.60 US$392,000
2025-09-19 2025-09-19 PlS Planned sale
3.6
Brown Hayden

President & CEO

Executive Director
20,000 -1.8%
20.00
US$400,000 		20,000 -1.8% 20.00 US$400,000
2025-09-22 2025-09-18 S Sale
3.6
Bottoms Dave

GM, Marketplace

Officer
10,894 -51.3%
19.16
US$208,779 		10,894 -51.3% 19.16 US$208,779
2025-09-22 2025-09-18 S Sale
3.6
Gessert Erica

Chief Financial Officer

Officer
8,730 -3.8%
19.16
US$167,303 		8,730 -3.8% 19.16 US$167,303
2025-09-19 2025-09-18 S Sale
3.6
Brown Hayden

President & CEO

Executive Director
22,344 -2.0%
19.16
US$428,198 		22,344 -2.0% 19.16 US$428,198
2025-09-19 2025-09-18 PlS Planned sale
3.6
Brown Hayden

President & CEO

Executive Director
20,000 -1.8%
19.00
US$380,000 		20,000 -1.8% 19.00 US$380,000
2025-09-18 2025-09-18 PrS Proposed sale
3.6
ERICA GESSERT

Officer

Officer
8,730
19.16
US$167,303 		8,730 19.16 US$167,303
2025-09-18 2025-09-18 PrS Proposed sale
3.6
HAYDEN BROWN

Officer; Director

Executive Director
22,344
19.16
US$428,203 		22,344 19.16 US$428,203
2025-09-18 2025-09-18 PrS Proposed sale
3.6
DAVID BOTTOMS

Officer

Officer
10,894
19.16
US$208,774 		10,894 19.16 US$208,774
2025-09-18 2025-09-18 PrS Proposed sale
3.6
HAYDEN L BROWN

Director; Officer

Executive Director
20,000
18.14
US$362,800 		20,000 18.14 US$362,800
2025-09-19 2025-09-17 PlS Planned sale
3.6
Brown Hayden

President & CEO

Executive Director
20,000 -1.8%
18.00
US$360,000 		20,000 -1.8% 18.00 US$360,000
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