Upland Software, Inc. (UPLD) has 20 known insider and institutional holders on record. The largest holder is MCDONALD JOHN T with 2,390,887 shares. Other notable holders include ESW Capital, LLC and Doman Dan.
Over the last 12 months, insiders have made 25 transactions in UPLD stock — 9 buys (valued at RSU Award) and 1 sells (valued at $34.06K). Insider buying has outpaced selling during this period, which may signal confidence in the company's prospects.
UPLD Insider Ownership
Top Holder
MCDONALD JOHN T
2,390,887 shares
Buys (12 mo)
9
$0.00 value
Sells (12 mo)
1
$34.06K value
12-Month Transaction Activity
Top Insider Holders
| # |
Name |
Role |
Shares Owned |
Last Filed |
Relative Size |
| 1 |
Mcdonald John T |
CEO |
2,390,887 |
2026-03-17 |
|
| 2 |
Esw Capital, Llc |
10 Percent Owner |
1,803,574 |
2021-05-24 |
|
| 3 |
Doman Dan |
Chief Operating & Product Ofcr |
923,766 |
2026-03-17 |
|
| 4 |
Epm Live, Inc. |
Officer |
854,400 |
2018-08-28 |
|
| 5 |
Wave Systems Corp |
10 Percent Owner |
661,166 |
2017-12-18 |
|
| 6 |
Mattox Timothy |
Director |
419,008 |
2025-10-29 |
|
| 7 |
Hill Michael Douglass |
CFO, Treasurer & Secretary |
392,291 |
2026-03-17 |
|
| 8 |
Favaron Rodney C |
President |
338,742 |
2022-06-21 |
|
| 9 |
Cummings Karen |
President and COO |
306,432 |
2025-07-01 |
|
| 10 |
Yates Oliver Robert Macfarlane |
Chief Sales Officer |
251,567 |
2024-03-19 |
|
| 11 |
Miller Paul Kenneth |
Chief Operating Officer |
209,387 |
2023-12-19 |
|
| 12 |
Gill Kinloch Iii |
CLO and Secretary |
194,590 |
2023-09-19 |
|
| 13 |
Global Undervalued Securities Master Fund Lp |
Officer |
192,708 |
2015-12-03 |
|
| 14 |
May David |
Director |
191,437 |
2025-10-29 |
|
| 15 |
Breslin Matthew |
Chief Revenue Officer |
150,000 |
2024-02-07 |
|
| 16 |
Walsh Teresa Miles |
Director |
144,490 |
2025-10-29 |
|
| 17 |
Smith Matthew Harnden |
General Counsel and Secretary |
131,908 |
2025-06-17 |
|
| 18 |
Chung David H S |
Director |
124,484 |
2025-10-29 |
|
| 19 |
Courter Stephen E |
Director |
124,232 |
2025-10-29 |
|
| 20 |
Ross Joe |
Director |
118,545 |
2023-08-02 |
|
Recent Transactions (last 12 months)
| Date |
Name |
Role |
Type |
Shares |
Price |
Value |
| 2026-03-16 |
Doman Dan |
Chief Operating & Product Ofcr |
Tax Withholding of RSU |
33,491 |
$0.54 |
$18.09K |
| 2026-03-16 |
Hill Michael Douglass |
CFO, Treasurer & Secretary |
Tax Withholding of RSU |
8,931 |
$0.54 |
$4.82K |
| 2026-03-16 |
Mcdonald John T |
CEO |
Tax Withholding of RSU |
18,605 |
$0.54 |
$10.05K |
| 2026-02-27 |
Doman Dan |
Chief Operating & Product Ofcr |
RSU Award |
100,000 |
- |
- |
| 2026-02-23 |
Doman Dan |
Chief Operating & Product Ofcr |
RSU Award |
150,000 |
- |
- |
| 2026-02-23 |
Hill Michael Douglass |
CFO, Treasurer & Secretary |
RSU Award |
70,000 |
- |
- |
| 2025-12-16 |
Doman Dan |
Chief Operating & Product Ofcr |
Tax Withholding of RSU |
24,595 |
$1.49 |
$36.52K |
| 2025-12-16 |
Hill Michael Douglass |
CFO, Treasurer & Secretary |
Tax Withholding of RSU |
8,856 |
$1.49 |
$13.15K |
| 2025-12-16 |
Mcdonald John T |
CEO |
Tax Withholding of RSU |
19,677 |
$1.49 |
$29.22K |
| 2025-10-27 |
Walsh Teresa Miles |
Director |
RSU Award |
25,000 |
- |
- |
| 2025-10-27 |
Mattox Timothy |
Director |
RSU Award |
25,000 |
- |
- |
| 2025-10-27 |
Chung David H S |
Director |
RSU Award |
25,000 |
- |
- |
| 2025-10-27 |
May David |
Director |
RSU Award |
25,000 |
- |
- |
| 2025-10-27 |
Courter Stephen E |
Director |
RSU Award |
25,000 |
- |
- |
| 2025-09-16 |
Doman Dan |
Chief Operating & Product Ofcr |
Tax Withholding of RSU |
26,236 |
$2.48 |
$65.07K |
| 2025-09-16 |
Hill Michael Douglass |
CFO, Treasurer & Secretary |
Tax Withholding of RSU |
11,152 |
$2.48 |
$27.66K |
| 2025-09-16 |
Mcdonald John T |
CEO |
Tax Withholding of RSU |
22,956 |
$2.48 |
$56.93K |
| 2025-09-11 |
Mcdonald John T |
CEO |
Informative Sell |
14,438 |
$2.36 |
$34.06K |
| 2025-06-30 |
Cummings Karen |
President and COO |
Tax Withholding of RSU |
40,993 |
$1.95 |
$79.94K |
| 2025-06-16 |
Doman Dan |
Chief Product Officer |
Tax Withholding of RSU |
14,758 |
$1.84 |
$27.15K |
| 2025-06-13 |
Doman Dan |
Chief Product Officer |
RSU Award |
350,000 |
- |
- |
| 2025-06-16 |
Smith Matthew Harnden |
General Counsel and Secretary |
Tax Withholding of RSU |
3,596 |
$1.84 |
$6.62K |
| 2025-06-16 |
Cummings Karen |
President and COO |
Tax Withholding of RSU |
11,479 |
$1.84 |
$21.12K |
| 2025-06-16 |
Hill Michael Douglass |
CFO & Treasurer |
Tax Withholding of RSU |
11,152 |
$1.84 |
$20.52K |
| 2025-06-16 |
Mcdonald John T |
CEO |
Tax Withholding of RSU |
22,957 |
$1.84 |
$42.24K |
