United States Software & IT Services

Upland Software Inc (UPLD)

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The most recent insider trading activity occurred on September 11, 2025, with a SELL transaction by CEO John T. McDonald for $34,063.57. Prior to this, on September 10, 2025, a PROPOSED_SALE by an Officer under the name John T. McDonald was reported. Earlier transactions in March 2025 and December 2024 involved planned and proposed sales by Timothy Mattox.
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Ticker: UPLD Exchange: NMS
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• Purchase • Sale • Planned purchase • Planned sale Net purchase Net sale Activity signal Earnings
Top insiders
Trades
MCDONALD JOHN T
CEO
1 sale — total 34,064 USD
Sale 11 Sep 2025
Value US$931,882.73 | Price 220.12 | Shares 62,147
Proposed sale 10 Sep 2025
Value US$4,396,844.55 | Price 330.47 | Shares 10,135
Proposed sale 17 Mar 2025
Value US$63,862.00 | Price 3.19 | Shares 20,000
Planned sale 17 Mar 2025
Value US$63,862.00 | Price 3.19 | Shares 20,000
Proposed sale 17 Dec 2024
Value US$12,612.39 | Price 4.56 | Shares 2,768
Planned sale 17 Dec 2024
Value US$12,612.39 | Price 4.56 | Shares 2,768
Sale 14 Nov 2024
Value US$45,061.20 | Price 2.50 | Shares 18,000
Sale 13 Nov 2024
Value US$5,271.60 | Price 2.64 | Shares 2,000
Proposed sale 13 Nov 2024
Value US$55,900.00 | Price 2.80 | Shares 20,000
Buy 9 Aug 2024
Value US$130,307.68 | Price 1.96 | Shares 66,365
Buy 8 Aug 2024
Value US$66,627.57 | Price 1.98 | Shares 33,635
Sale 21 Nov 2023
Value US$90,625.54 | Price 4.43 | Shares 20,448
Proposed sale 21 Nov 2023
Value US$87,679.54 | Price 4.78 | Shares 18,343
Sale 7 Nov 2023
Value US$67,242.38 | Price 4.80 | Shares 13,996
Proposed sale 7 Nov 2023
Value US$62,562.12 | Price 4.47 | Shares 13,996
Buy 13 Mar 2023
Value US$47,500.00 | Price 4.75 | Shares 10,000
Buy 10 Mar 2023
Value US$48,000.00 | Price 4.80 | Shares 10,000
Planned sale 19 Dec 2022
Value US$47,120.32 | Price 7.52 | Shares 6,266
Planned sale 7 Nov 2022
Value US$60,756.00 | Price 7.32 | Shares 8,300
Planned sale 13 Oct 2022
Value US$24,710.00 | Price 7.06 | Shares 3,500
Planned sale 12 Oct 2022
Value US$25,795.00 | Price 7.37 | Shares 3,500
Buy 23 Aug 2022
Value US$113,307.00 | Price 11.33 | Shares 10,000
Buy 22 Aug 2022
Value US$109,940.00 | Price 10.99 | Shares 10,000
Buy 19 Aug 2022
Value US$214,660.00 | Price 10.73 | Shares 20,000
Buy 18 Aug 2022
Value US$111,000.00 | Price 11.10 | Shares 10,000
Buy 17 Aug 2022
Value US$113,300.00 | Price 11.33 | Shares 10,000
Buy 15 Aug 2022
Value US$112,200.00 | Price 11.22 | Shares 10,000
Buy 12 Aug 2022
Value US$113,900.00 | Price 11.39 | Shares 10,000
Buy 11 Aug 2022
Value US$112,300.00 | Price 11.23 | Shares 10,000
Sale 9 Aug 2022
Value US$187,745.08 | Price 11.21 | Shares 16,748
Sale 18 Nov 2021
Value US$76,477.57 | Price 21.97 | Shares 3,481
Sale 21 Jun 2021
Value US$2,062.95 | Price 40.45 | Shares 51
Planned sale 21 Jun 2021
Value US$307,011.08 | Price 41.50 | Shares 7,398
Planned sale 18 Jun 2021
Value US$424,447.87 | Price 41.12 | Shares 10,322
Planned sale 17 Mar 2021
Value US$163,783.20 | Price 48.75 | Shares 3,360
Planned sale 17 Mar 2021
Value US$316,542.34 | Price 48.14 | Shares 6,576
Planned sale 17 Mar 2021
Value US$206,594.00 | Price 48.73 | Shares 4,240
Planned sale 17 Mar 2021
Value US$319,551.64 | Price 48.15 | Shares 6,637
Planned sale 17 Mar 2021
Value US$118,971.90 | Price 48.74 | Shares 2,441
Planned sale 17 Mar 2021
Value US$230,836.10 | Price 48.14 | Shares 4,795
Planned sale 1 Mar 2021
Value US$501,653.00 | Price 50.17 | Shares 10,000
Planned sale 1 Mar 2021
Value US$5,105.00 | Price 51.05 | Shares 100
Planned sale 1 Mar 2021
Value US$495,410.85 | Price 50.04 | Shares 9,900
Planned sale 11 Feb 2021
Value US$744,848.84 | Price 50.73 | Shares 14,684
Planned sale 11 Feb 2021
Value US$228,633.00 | Price 51.00 | Shares 4,483
Planned sale 10 Feb 2021
Value US$195,089.40 | Price 50.10 | Shares 3,894
Planned sale 9 Feb 2021
Value US$2,234,006.70 | Price 50.32 | Shares 44,393
Planned sale 8 Feb 2021
Value US$64,251.03 | Price 50.00 | Shares 1,285
Planned sale 8 Feb 2021
Value US$585,983.29 | Price 50.37 | Shares 11,633
Planned sale 8 Feb 2021
Value US$1,052,287.13 | Price 51.00 | Shares 20,633
Planned sale 5 Feb 2021
Value US$234,916.59 | Price 51.00 | Shares 4,606
Planned sale 5 Feb 2021
Value US$3,163,698.67 | Price 50.71 | Shares 62,392
Planned sale 5 Feb 2021
Value US$759,084.00 | Price 51.00 | Shares 14,884
Planned sale 4 Feb 2021
Value US$564,015.77 | Price 50.01 | Shares 11,277
Planned sale 4 Feb 2021
Value US$354,212.40 | Price 50.03 | Shares 7,080
Planned sale 2 Feb 2021
Value US$679,806.28 | Price 50.03 | Shares 13,588
Planned sale 2 Feb 2021
Value US$1,120,313.29 | Price 50.05 | Shares 22,385
Planned sale 27 Jan 2021
Value US$85,010.20 | Price 50.01 | Shares 1,700
Planned sale 27 Jan 2021
Value US$111,300.00 | Price 50.00 | Shares 2,226
Planned sale 25 Jan 2021
Value US$1,311,867.66 | Price 50.04 | Shares 26,219
Planned sale 25 Jan 2021
Value US$353,605.04 | Price 50.09 | Shares 7,060
Planned sale 22 Jan 2021
Value US$376,300.00 | Price 50.00 | Shares 7,526
Planned sale 22 Jan 2021
Value US$22,500.00 | Price 50.00 | Shares 450
Planned sale 21 Jan 2021
Value US$50,000.00 | Price 50.00 | Shares 1,000
Planned sale 21 Jan 2021
Value US$47,050.00 | Price 50.00 | Shares 941
Planned sale 22 Dec 2020
Value US$223,987.60 | Price 47.46 | Shares 4,720
Planned sale 22 Dec 2020
Value US$677,840.90 | Price 46.77 | Shares 14,494
Planned sale 22 Dec 2020
Value US$313,302.00 | Price 47.00 | Shares 6,666
Planned sale 22 Dec 2020
Value US$129,486.55 | Price 47.52 | Shares 2,725
Planned sale 22 Dec 2020
Value US$509,652.69 | Price 46.77 | Shares 10,897
Planned sale 22 Dec 2020
Value US$137,744.20 | Price 47.50 | Shares 2,900
Planned sale 22 Dec 2020
Value US$471,545.22 | Price 46.77 | Shares 10,082
Planned sale 22 Dec 2020
Value US$76,243.92 | Price 47.50 | Shares 1,605
Planned sale 22 Dec 2020
Value US$257,430.32 | Price 46.76 | Shares 5,505
Planned sale 17 Dec 2020
Value US$510,514.00 | Price 47.00 | Shares 10,862
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
2025-09-11 2025-09-11 S Sale
1.4
MCDONALD JOHN T

CEO

Executive Director
62,147 -49.1%
220.12
US$931,883 		62,147 -49.1% 220.12 US$931,883
2025-09-10 2025-09-10 PrS Proposed sale
1.4
MCDONALD JOHN T

Officer

Officer
10,135
330.47
US$4,396,845 		10,135 330.47 US$4,396,845
2025-03-17 2025-03-17 PrS Proposed sale
1.5
TIMOTHY WILLIAM MATTOX

Director

Non-Executive Director
39,423
391.07
US$2,300,388 		39,423 391.07 US$2,300,388
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
2020-12-23 2020-12-22 PlS Planned sale
Favaron Rodney C

co-President and CCO

Officer
4,720 -3.5%
47.46
US$223,988 		4,720 -3.5% 47.46 US$223,988
2020-12-23 2020-12-22 PlS Planned sale
Favaron Rodney C

co-President and CCO

Officer
14,494 -9.7%
46.77
US$677,841 		14,494 -9.7% 46.77 US$677,841
2020-12-23 2020-12-22 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
2,725 -0.2%
47.52
US$129,487 		2,725 -0.2% 47.52 US$129,487
2020-12-23 2020-12-22 PlS Planned sale
1.4
MCDONALD JOHN T

CEO

Executive Director
10,897 -0.7%
46.77
US$509,653 		10,897 -0.7% 46.77 US$509,653
2020-12-23 2020-12-22 PlS Planned sale
1.5
Mattox Timothy

co-President & COO

Officer
2,900 -0.6%
47.50
US$137,744 		2,900 -0.6% 47.50 US$137,744
2020-12-23 2020-12-22 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
1,605 -0.6%
47.50
US$76,244 		1,605 -0.6% 47.50 US$76,244
2020-12-23 2020-12-22 PlS Planned sale
1.5
Mattox Timothy

co-President & COO

Officer
10,082 -2.1%
46.77
US$471,545 		10,082 -2.1% 46.77 US$471,545
2020-12-23 2020-12-22 PlS Planned sale
Favaron Rodney C

co-President and CCO

Officer
6,666 -4.3%
47.00
US$313,302 		6,666 -4.3% 47.00 US$313,302
2020-12-23 2020-12-22 PlS Planned sale
0.6
Hill Michael Douglass

CFO &Treasurer

Officer
5,505 -2.1%
46.76
US$257,430 		5,505 -2.1% 46.76 US$257,430
2020-12-21 2020-12-17 PlS Planned sale
Favaron Rodney C

co-President and CCO

Officer
10,862 -6.5%
47.00
US$510,514 		10,862 -6.5% 47.00 US$510,514
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