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Upland Software, Inc.

UPLD Net selling
CIK 0001505155 #5179 in the set updated 17 Sep 2026
Bought (120 mo)
$1.73M
out of their own pocket, the only kind of buying there is
Sold (120 mo)
$162.70M
$102.16K on a plan · $4.79M straight out of an exercise
Sold at will
$157.81M
166 of 178 sales
Net
−$160.97M
−$156.08M against sales at will

By person

24 insiders · 199 transactions
30.9×

John T. (Jack) McDonald holds 30.9 times base salary in stock. $15.49M of shares against $500.00K in salary for 2025.

Salary from the company's own proxy. The shares are what John T. (Jack) McDonald last reported holding, valued at $4.28, the price Common Stock was last bought or sold at on the open market here, on 7 Aug 2026.

Insider
Role
Bought
Sold
Net
Holding
Worth
Change
WAVE SYSTEMS CORP entity
10% owner
$63.91M (13)
−$63.91M
2,803,574
$12.00M
−50.6%
EPM Live, Inc. entity
Member of 10% owner group
$34.99M (11)
−$34.99M
1,803,574
$7.72M
−35.7%
MCDONALD JOHN T
Director
$1.29M (12)
$30.58M (55)
−$29.29M
3,619,577
$15.49M
+34.4%
Hill Michael Douglass
CFO, Treasurer & Secretary
$11.49M (33)
−$11.49M
543,402
$2.33M
+113.9%
Mattox Timothy
Director
$10.48M (31)
−$10.48M
36,053
$154.31K
Favaron Rodney C
President
$5.70M (13) scheduled
−$5.70M
338,742
$1.45M
+3,152%
MAY DAVID
Director
$423.14K (2)
$4.51M (9)
−$4.08M
200,437
$857.89K
+23.0%
Gill Kinloch III
CLO and Secretary
$491.23K (5)
−$491.23K
194,590
$832.86K
+149.8%
COURTER STEPHEN E
Director
$243.17K (5)
−$243.17K
124,232
$531.73K
+1,093%
Burk Ian
Chief Business Officer
$234.87K (2)
−$234.87K
107,047
$458.17K
+20.5%
Doman Dan
Chief Operating & Product Ofcr
$67.24K (1)
−$67.24K
894,251
$3.83M
+769.2%
ESW Capital, LLC entity
10% owner
$12.00K (1)
+$12.00K
5,750,646
$24.61M
0.0%
Nathaniel Sean
CEO and President
502,146
$2.15M
+2,320%
Cummings Karen
President and COO
306,432
$1.31M
+16.0%
Yates Oliver Robert MacFarlane
Chief Sales Officer
251,567
$1.08M
+95.4%
Miller Paul Kenneth
Chief Operating Officer
209,387
$896.20K
+120.4%
Breslin Matthew
Chief Revenue Officer
150,000
$642.02K
Walsh Teresa Miles
Director
144,490
$618.43K
Smith Matthew Harnden
General Counsel and Secretary
131,908
$564.58K
Chung David H S
Director
124,484
$532.80K
Ross Joe
Director
118,545
$507.38K
+382.0%
Simon Jennifer L.
Chief Financial Officer
30,000
$128.40K
THORNTON JOHN D
10% owner
0
$0.00
−100.0%
AV Partners IX LLC entity
10% owner
0
$0.00
−100.0%

No percentages here. This company's share count has moved by a factor of 9.9 over the window, from 2,957,191 to 29,363,201 shares. A split, a merger or a large issue changes what the company is, and a holding measured at one point in that run is not a fraction of it at another.

Insider
Date
Role
Action
Shares
Price
Amount
MCDONALD JOHN T
9 Aug 2024
CEO
Buy indirect
66,365
$1.96
$130.31K
MCDONALD JOHN T
8 Aug 2024
CEO
Buy indirect
33,635
$1.98
$66.63K
MCDONALD JOHN T
13 Mar 2023
CEO
Buy indirect
10,000
$4.75
$47.50K
MCDONALD JOHN T
10 Mar 2023
CEO
Buy indirect
10,000
$4.80
$48.00K
MCDONALD JOHN T
23 Aug 2022
CEO
Buy indirect
10,000
$11.33
$113.31K
MCDONALD JOHN T
22 Aug 2022
CEO
Buy indirect
10,000
$10.99
$109.94K
MCDONALD JOHN T
19 Aug 2022
CEO
Buy indirect
20,000
$10.73
$214.66K
MCDONALD JOHN T
18 Aug 2022
CEO
Buy indirect
10,000
$11.10
$111.00K
MCDONALD JOHN T
17 Aug 2022
CEO
Buy indirect
10,000
$11.33
$113.30K
MCDONALD JOHN T
15 Aug 2022
CEO
Buy indirect
10,000
$11.22
$112.20K
MCDONALD JOHN T
12 Aug 2022
CEO
Buy indirect
10,000
$11.39
$113.90K
MCDONALD JOHN T
11 Aug 2022
CEO
Buy indirect
10,000
$11.23
$112.30K
MAY DAVID
17 Aug 2020
Director
Buy indirect
10,000
$33.72
$337.24K
MAY DAVID
16 Nov 2016
Director
Buy
10,000
$8.59
$85.90K
ESW Capital, LLC
4 Nov 2016
10% owner
Buy
1,500
$8.00
$12.00K

What was left out

Form 4 filings counted 340
Amendments (4/A) skipped 9
Filings about a different issuer 0
Unreadable filings 0
Joint filings 13
Sales on a Rule 10b5-1 plan 8
Sales straight out of an exercise 4
Sales at will 166
Transactions with no price 0
Shares from compensation/vesting 22,395,662
Sales filed before the plan box existed 161
History held since 18 Nov 2016