United States Software & IT Services

Upland Software Inc (UPLD)

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Over the past 90 days, Upland Software Inc. has seen seven insider transactions, all involving sales by Director Timothy William Mattox. These transactions totaled $31,050 in value. This activity follows the company's recent earnings report, which showed an EPS beat of 275%, amid a 55.9% decline in the stock price over the last quarter.
Ticker: UPLD Exchange: NMS
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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 Upland Software Inc. Upgrade to see score, net flow, insiders and the full signal context.

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Proposed sale 6 Aug 2026
Value US$3,437,745.10 | Price 325.61 | Shares 66,456
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
2026-08-06 2026-08-06 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
66,456
325.61
US$3,437,745 		66,456 325.61 US$3,437,745
2026-08-06 2026-08-05 PlS Planned sale
1.5
Mattox Timothy
Non-Executive Director
94,784 +6.6%
445.79
US$72,249 		94,784 +6.6% 445.79 US$72,249
2026-08-05 2026-08-05 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
58,072
249.20
US$3,856,078 		58,072 249.20 US$3,856,078
2026-08-06 2026-08-04 PlS Planned sale
1.5
Mattox Timothy
Non-Executive Director
1,000 -2.5%
4.33
US$100,000 		1,000 -2.5% 4.33 US$100,000
2026-08-04 2026-08-04 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
1,000
4.33
US$100,000 		1,000 4.33 US$100,000
2026-08-04 2026-08-04 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
1,000
4.33
US$100,000 		1,000 4.33 US$100,000
2026-08-04 2026-08-03 PlS Planned sale
1.5
Mattox Timothy
Non-Executive Director
1,000 -2.4%
4.45
US$100,000 		1,000 -2.4% 4.45 US$100,000
2026-08-03 2026-08-03 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
1,000
4.45
US$100,000 		1,000 4.45 US$100,000
2026-08-04 2026-07-31 PlS Planned sale
1.5
Mattox Timothy
Non-Executive Director
1,000 -2.4%
4.48
US$100,000 		1,000 -2.4% 4.48 US$100,000
2026-07-31 2026-07-31 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
1,000
4.48
US$100,000 		1,000 4.48 US$100,000
2025-09-11 2025-09-11 S Sale
1.4
MCDONALD JOHN T

CEO

Executive Director
14,438 -0.6%
2.36
US$34,064 		14,438 -0.6% 2.36 US$34,064
2025-09-10 2025-09-10 PrS Proposed sale
1.4
MCDONALD JOHN T

Officer

Officer
15,000
2.31
US$34,650 		15,000 2.31 US$34,650
2025-03-17 2025-03-17 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
20,000
3.19
US$63,862 		20,000 3.19 US$63,862
2025-03-17 2025-03-17 PlS Planned sale
1.5
Mattox Timothy
Non-Executive Director
20,000 -4.8%
3.19
US$63,862 		20,000 -4.8% 3.19 US$63,862
2024-12-17 2024-12-17 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
2,768
4.56
US$12,612 		2,768 4.56 US$12,612
2024-12-17 2024-12-17 PlS Planned sale
1.5
Mattox Timothy
Non-Executive Director
2,768 -0.7%
4.56
US$12,612 		2,768 -0.7% 4.56 US$12,612
2024-11-15 2024-11-14 S Sale
1.5
Mattox Timothy
Non-Executive Director
18,000 -4.1%
2.50
US$45,061 		18,000 -4.1% 2.50 US$45,061
2024-11-15 2024-11-13 S Sale
1.5
Mattox Timothy
Non-Executive Director
2,000 -0.5%
2.64
US$5,272 		2,000 -0.5% 2.64 US$5,272
2024-11-13 2024-11-13 PrS Proposed sale
1.5
Mattox Timothy

Director

Non-Executive Director
20,000
2.80
US$55,900 		20,000 2.80 US$55,900
2024-08-12 2024-08-09 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
66,365 +22.3%
1.96
US$130,308 		66,365 +22.3% 1.96 US$130,308
2024-08-12 2024-08-08 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
33,635 +12.8%
1.98
US$66,628 		33,635 +12.8% 1.98 US$66,628
2023-11-22 2023-11-21 S Sale
3.4
COURTER STEPHEN E
Non-Executive Director
20,448 -21.6%
4.43
US$90,626 		20,448 -21.6% 4.43 US$90,626
2023-11-21 2023-11-21 PrS Proposed sale
3.4
COURTER STEPHEN E

Director

Non-Executive Director
18,343
4.78
US$87,680 		18,343 4.78 US$87,680
2023-11-09 2023-11-07 S Sale
3.0
Doman Dan

Chief Product Officer

Officer
13,996 -6.5%
4.80
US$67,242 		13,996 -6.5% 4.80 US$67,242
2023-11-07 2023-11-07 PrS Proposed sale
3.0
Doman Dan

Officer

Officer
13,996
4.47
US$62,562 		13,996 4.47 US$62,562
2023-03-14 2023-03-13 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +3.9%
4.75
US$47,500 		10,000 +3.9% 4.75 US$47,500
2023-03-14 2023-03-10 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +4.1%
4.80
US$48,000 		10,000 +4.1% 4.80 US$48,000
2022-12-20 2022-12-19 PlS Planned sale
3.3
Burk Ian

Chief Business Officer

Officer
6,266 -5.5%
7.52
US$47,120 		6,266 -5.5% 7.52 US$47,120
2022-11-09 2022-11-07 PlS Planned sale
3.1
Gill Kinloch III

CLO and Secretary

Officer
8,300 -6.4%
7.32
US$60,756 		8,300 -6.4% 7.32 US$60,756
2022-10-14 2022-10-13 PlS Planned sale
3.4
COURTER STEPHEN E
Non-Executive Director
3,500 -9.9%
7.06
US$24,710 		3,500 -9.9% 7.06 US$24,710
2022-10-14 2022-10-12 PlS Planned sale
3.4
COURTER STEPHEN E
Non-Executive Director
3,500 -9.0%
7.37
US$25,795 		3,500 -9.0% 7.37 US$25,795
2022-08-25 2022-08-23 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +4.3%
11.33
US$113,307 		10,000 +4.3% 11.33 US$113,307
2022-08-23 2022-08-22 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +4.5%
10.99
US$109,940 		10,000 +4.5% 10.99 US$109,940
2022-08-23 2022-08-19 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
20,000 +9.8%
10.73
US$214,660 		20,000 +9.8% 10.73 US$214,660
2022-08-19 2022-08-18 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +5.2%
11.10
US$111,000 		10,000 +5.2% 11.10 US$111,000
2022-08-19 2022-08-17 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +5.4%
11.33
US$113,300 		10,000 +5.4% 11.33 US$113,300
2022-08-17 2022-08-15 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +5.8%
11.22
US$112,200 		10,000 +5.8% 11.22 US$112,200
2022-08-15 2022-08-12 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +6.1%
11.39
US$113,900 		10,000 +6.1% 11.39 US$113,900
2022-08-15 2022-08-11 B Purchase
1.4
MCDONALD JOHN T

CEO

Executive Director
10,000 +6.5%
11.23
US$112,300 		10,000 +6.5% 11.23 US$112,300
2022-08-11 2022-08-09 S Sale
3.3
Burk Ian

Chief Business Officer

Officer
16,748 -18.9%
11.21
US$187,745 		16,748 -18.9% 11.21 US$187,745
2021-11-22 2021-11-18 S Sale
3.1
Gill Kinloch III

EVP, CLO and Secretary

Officer
3,481 -5.0%
21.97
US$76,478 		3,481 -5.0% 21.97 US$76,478
2021-06-21 2021-06-21 S Sale
1.4
MCDONALD JOHN T

CEO

Executive Director
51 -0.0%
40.45
US$2,063 		51 -0.0% 40.45 US$2,063
2021-06-21 2021-06-21 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
7,398 -2.8%
41.50
US$307,011 		7,398 -2.8% 41.50 US$307,011
2021-06-21 2021-06-18 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
10,322 -0.8%
41.12
US$424,448 		10,322 -0.8% 41.12 US$424,448
2021-03-19 2021-03-17 PlS Planned sale
Favaron Rodney C

President

Officer
3,360 -1.2%
48.75
US$163,783 		3,360 -1.2% 48.75 US$163,783
2021-03-19 2021-03-17 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
4,240 -0.3%
48.73
US$206,594 		4,240 -0.3% 48.73 US$206,594
2021-03-19 2021-03-17 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
2,441 -0.9%
48.74
US$118,972 		2,441 -0.9% 48.74 US$118,972
2021-03-19 2021-03-17 PlS Planned sale
Favaron Rodney C

President

Officer
6,576 -2.3%
48.14
US$316,542 		6,576 -2.3% 48.14 US$316,542
2021-03-19 2021-03-17 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
6,637 -0.5%
48.15
US$319,552 		6,637 -0.5% 48.15 US$319,552
2021-03-19 2021-03-17 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
4,795 -1.8%
48.14
US$230,836 		4,795 -1.8% 48.14 US$230,836
2021-03-03 2021-03-01 PlS Planned sale
3.2
MAY DAVID
Non-Executive Director
10,000 -100.0%
50.17
US$501,653 		10,000 -100.0% 50.17 US$501,653
2021-03-03 2021-03-01 PlS Planned sale
3.2
MAY DAVID
Non-Executive Director
100 -0.2%
51.05
US$5,105 		100 -0.2% 51.05 US$5,105
2021-03-03 2021-03-01 PlS Planned sale
3.2
MAY DAVID
Non-Executive Director
9,900 -15.3%
50.04
US$495,411 		9,900 -15.3% 50.04 US$495,411
2021-02-12 2021-02-11 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
14,684 -1.1%
50.73
US$744,849 		14,684 -1.1% 50.73 US$744,849
2021-02-12 2021-02-11 PlS Planned sale
1.5
Mattox Timothy

co-President & COO

Officer
4,483 -1.0%
51.00
US$228,633 		4,483 -1.0% 51.00 US$228,633
2021-02-12 2021-02-10 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
3,894 -0.3%
50.10
US$195,089 		3,894 -0.3% 50.10 US$195,089
2021-02-09 2021-02-09 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
44,393 -3.2%
50.32
US$2,234,007 		44,393 -3.2% 50.32 US$2,234,007
2021-02-09 2021-02-08 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
1,285 -0.1%
50.00
US$64,251 		1,285 -0.1% 50.00 US$64,251
2021-02-09 2021-02-08 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
11,633 -0.8%
50.37
US$585,983 		11,633 -0.8% 50.37 US$585,983
2021-02-09 2021-02-08 PlS Planned sale
1.5
Mattox Timothy

co-President & COO

Officer
20,633 -4.5%
51.00
US$1,052,287 		20,633 -4.5% 51.00 US$1,052,287
2021-02-09 2021-02-05 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
4,606 -0.3%
51.00
US$234,917 		4,606 -0.3% 51.00 US$234,917
2021-02-09 2021-02-05 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
62,392 -4.3%
50.71
US$3,163,699 		62,392 -4.3% 50.71 US$3,163,699
2021-02-09 2021-02-05 PlS Planned sale
1.5
Mattox Timothy

co-President & COO

Officer
14,884 -3.1%
51.00
US$759,084 		14,884 -3.1% 51.00 US$759,084
2021-02-04 2021-02-04 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
11,277 -5.2%
50.01
US$564,016 		11,277 -5.2% 50.01 US$564,016
2021-02-04 2021-02-04 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
7,080 -0.5%
50.03
US$354,212 		7,080 -0.5% 50.03 US$354,212
2021-02-04 2021-02-02 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
13,588 -0.9%
50.03
US$679,806 		13,588 -0.9% 50.03 US$679,806
2021-02-04 2021-02-02 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
22,385 -9.3%
50.05
US$1,120,313 		22,385 -9.3% 50.05 US$1,120,313
2021-01-29 2021-01-27 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
1,700 -0.1%
50.01
US$85,010 		1,700 -0.1% 50.01 US$85,010
2021-01-29 2021-01-27 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
2,226 -0.9%
50.00
US$111,300 		2,226 -0.9% 50.00 US$111,300
2021-01-25 2021-01-25 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
26,219 -1.7%
50.04
US$1,311,868 		26,219 -1.7% 50.04 US$1,311,868
2021-01-25 2021-01-25 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
7,060 -2.8%
50.09
US$353,605 		7,060 -2.8% 50.09 US$353,605
2021-01-25 2021-01-22 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
7,526 -0.5%
50.00
US$376,300 		7,526 -0.5% 50.00 US$376,300
2021-01-25 2021-01-22 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
450 -0.2%
50.00
US$22,500 		450 -0.2% 50.00 US$22,500
2021-01-25 2021-01-21 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
1,000 -0.1%
50.00
US$50,000 		1,000 -0.1% 50.00 US$50,000
2021-01-25 2021-01-21 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
941 -0.4%
50.00
US$47,050 		941 -0.4% 50.00 US$47,050
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