Upland Software Inc. (UPLD) - Insider Trading & Ownership

Real time insider trading transaction history:

  • Insiders are prohibited from making short-swing profits by trading their shares within 6 months of the registration or acquiring the shares.
  • Shares are not adjusted for stock split.
"Insiders might sell their shares for any number of reasons, but they buy them for only one: they think the price will rise"
- Peter Lynch
What is insider trading>>
Time period
Insider Trading Transactions for Upland Software Inc.
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Common stock purchase or sale:
Transaction
Date
Reported
DateTime
CompanySymbolInsider
Relationship
Shares
Traded
Average
Price
Total
Amount
Shares
Owned
Filing
2026-08-07
Sale
2026-08-11
4:54 pm
Upland Software Inc.UPLDMattox Timothy
Director
847$4.2801$3,62736,053
(Direct)
View
2026-08-06
Sale
2026-08-10
5:36 pm
Upland Software Inc.UPLDMattox Timothy
Director
1,000$4.27$4,27036,900
(Direct)
View
2026-08-04
Sale
2026-08-06
4:55 pm
Upland Software Inc.UPLDMattox Timothy
Director
2,000$4.43$8,86037,900
(Direct)
View
2026-07-31
Sale
2026-08-04
5:46 pm
Upland Software Inc.UPLDMattox Timothy
Director
2,000$4.465$8,93039,900
(Direct)
View
2025-09-11
Sale
2025-09-11
5:50 pm
Upland Software Inc.UPLDMCDONALD JOHN T
CEO
14,438$2.3593$34,0642,815,863
(Indirect
Direct)
View
2025-03-17
Sale
2025-03-17
5:26 pm
Upland Software Inc.UPLDMattox Timothy
Director
20,000$3.1931$63,862394,008
(Direct)
View

Stock options: Exercise, Award, Grant, Conversion
Transaction
Date
Reported
DateTime
Exercisable
Expiration
CompanySymnbolInsider
Relationship
Shares
Traded
Conversion
Price
Shares
Owned
Filing
2026-08-17
Option Award
2026-08-18
4:25 pm
N/A
2029-08-16
Upland Software Inc.UPLDSimon Jennifer L.
Chief Financial Officer
36,666$036,666
(Direct)
View

Ownership
2026-08-03
5:00 pm
N/A
N/A
Upland Software Inc.UPLDTamez David
Interim CFO
0$06,947
(Direct)
View
2026-06-16
Tax Withholding
2026-06-16
6:34 pm
N/A
N/A
Upland Software Inc.UPLDHill Michael Douglass
CFO, Treasurer & Secretary
8,931$0.6064543,402
(Direct)
View
2026-06-16
Tax Withholding
2026-06-16
6:33 pm
N/A
N/A
Upland Software Inc.UPLDNathaniel Sean
CEO and President
18,605$0.6064502,146
(Direct)
View
2026-06-16
Tax Withholding
2026-06-16
6:32 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Operating & Product Ofcr
29,515$0.6064894,251
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:51 pm
N/A
2029-05-01
Upland Software Inc.UPLDNathaniel Sean
CEO and President
633,333$0654,084
(Direct)
View
2026-04-30
Option Award
2026-05-04
4:50 pm
N/A
N/A
Upland Software Inc.UPLDMCDONALD JOHN T
Director
250,000$03,004,625
(Direct)
View

Ownership
2026-05-04
4:49 pm
N/A
N/A
Upland Software Inc.UPLDNathaniel Sean
CEO and President
0$020,751
(Direct)
View
2026-03-16
Tax Withholding
2026-03-17
4:33 pm
N/A
N/A
Upland Software Inc.UPLDMCDONALD JOHN T
CEO
18,605$0.542,754,625
(Direct)
View
2026-03-16
Tax Withholding
2026-03-17
4:31 pm
N/A
N/A
Upland Software Inc.UPLDHill Michael Douglass
CFO, Treasurer & Secretary
8,931$0.54552,333
(Direct)
View
2026-03-16
Tax Withholding
2026-03-17
4:30 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Operating & Product Ofcr
33,491$0.54923,766
(Direct)
View
2026-02-27
Option Award
2026-03-03
6:00 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Operating & Product Ofcr
100,000$0957,257
(Direct)
View
2026-02-23
Option Award
2026-02-25
5:53 pm
N/A
N/A
Upland Software Inc.UPLDHill Michael Douglass
CFO, Treasurer & Secretary
70,000$0561,264
(Direct)
View
2026-02-23
Option Award
2026-02-25
5:51 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Operating & Product Ofcr
150,000$0857,257
(Direct)
View
2025-12-16
Tax Withholding
2025-12-17
4:30 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Operating & Product Ofcr
24,595$1.485707,257
(Direct)
View
2025-12-16
Tax Withholding
2025-12-17
4:28 pm
N/A
N/A
Upland Software Inc.UPLDMCDONALD JOHN T
CEO
19,677$1.4852,773,230
(Direct)
View
2025-12-16
Tax Withholding
2025-12-17
4:27 pm
N/A
N/A
Upland Software Inc.UPLDHill Michael Douglass
CFO, Treasurer & Secretary
8,856$1.485491,264
(Direct)
View
2025-10-27
Option Award
2025-10-29
4:41 pm
N/A
N/A
Upland Software Inc.UPLDChung David H S
Director
25,000$0124,484
(Direct)
View
2025-10-27
Option Award
2025-10-29
4:38 pm
N/A
N/A
Upland Software Inc.UPLDCOURTER STEPHEN E
Director
25,000$0124,232
(Direct)
View
2025-10-27
Option Award
2025-10-29
4:36 pm
N/A
N/A
Upland Software Inc.UPLDMattox Timothy
Director
25,000$0419,008
(Direct)
View
2025-10-27
Option Award
2025-10-29
4:32 pm
N/A
N/A
Upland Software Inc.UPLDMAY DAVID
Director
25,000$0191,437
(Direct)
View
2025-10-27
Option Award
2025-10-29
4:31 pm
N/A
N/A
Upland Software Inc.UPLDWalsh Teresa Miles
Director
25,000$0144,490
(Direct)
View
2025-09-16
Tax Withholding
2025-09-17
5:29 pm
N/A
N/A
Upland Software Inc.UPLDMCDONALD JOHN T
CEO
22,956$2.482,792,907
(Direct)
View
2025-09-16
Tax Withholding
2025-09-17
5:26 pm
N/A
N/A
Upland Software Inc.UPLDHill Michael Douglass
CFO, Treasurer & Secretary
11,152$2.48500,120
(Direct)
View
2025-09-16
Tax Withholding
2025-09-17
5:24 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Operating & Product Ofcr
26,236$2.48731,852
(Direct)
View
2025-06-30
Tax Withholding
2025-07-01
4:57 pm
N/A
N/A
Upland Software Inc.UPLDCummings Karen
President and COO
40,993$1.95306,432
(Direct)
View
2025-06-16
Tax Withholding
2025-06-17
4:18 pm
N/A
N/A
Upland Software Inc.UPLDSmith Matthew Harnden
General Counsel and Secretary
3,596$1.84131,908
(Direct)
View
2025-06-16
Tax Withholding
2025-06-17
4:17 pm
N/A
N/A
Upland Software Inc.UPLDMCDONALD JOHN T
CEO
22,957$1.842,830,301
(Direct)
View
2025-06-16
Tax Withholding
2025-06-17
4:16 pm
N/A
N/A
Upland Software Inc.UPLDHill Michael Douglass
CFO & Treasurer
11,152$1.84511,272
(Direct)
View
2025-06-16
Tax Withholding
2025-06-17
4:16 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Product Officer
14,758$1.84758,088
(Direct)
View
2025-06-13
Option Award
2025-06-17
4:16 pm
N/A
N/A
Upland Software Inc.UPLDDoman Dan
Chief Product Officer
350,000$0758,088
(Direct)
View
2025-06-16
Tax Withholding
2025-06-17
4:14 pm
N/A
N/A
Upland Software Inc.UPLDCummings Karen
President and COO
11,479$1.84347,425
(Direct)
View
2025-03-16
Tax Withholding
2025-03-17
5:25 pm
N/A
N/A
Upland Software Inc.UPLDSmith Matthew Harnden
General Counsel and Secretary
4,135$3.1135,504
(Direct)
View
2025-03-16
Tax Withholding
2025-03-17
5:24 pm
N/A
N/A
Upland Software Inc.UPLDMCDONALD JOHN T
CEO
24,273$3.12,853,258
(Direct)
View
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