Quick Takeaways
- UPLD - Upland Software, Inc. has 19 insiders with reported activity on this page.
- Net insider value flow over the last year: -$34,064.
- Recent transaction rows are available for direct filing-level review.
- Info
- Insider Trading
- Financials
- Holders
Insider Transactions Reported by 19 Insiders of Upland Software, Inc.
- Symbol
- UPLD on Nasdaq
- Location
- Austin, TX
What Changed
- Buy value: ; sell value: $34,063.
- Net share flow: -14,438.
Why This Matters
- This page gives a plain-language issuer insider context before you inspect transaction-level evidence.
- Use the filing links below to verify timestamps, codes, and ownership impacts directly from SEC forms.
Official SEC Source
Insider trading overview
Last 12 monthsNet insider flow leans to selling over the last 12 months. Net value: -$34,064.
Buys
$0
Shares: 0
Insiders: 0
Sells
$34,064
Shares: 14,438
Insiders: 1
Net
-$34,064
Shares: -14,438
Insiders: -1
| Window (months) | Buy shares | Sell shares | Buy $ | Sell $ | Net $ |
|---|---|---|---|---|---|
| 0-3 | 0 | 0 | $0 | $0 | $0 |
| 3-6 | 0 | 0 | $0 | $0 | $0 |
| 6-9 | 0 | 14,438 | $0 | $34,064 | -$34,064 |
| 9-12 | 0 | 0 | $0 | $0 | $0 |
Upland Software, Inc. executives and other stock owners filed with the SEC include:
| Name | Relationship | Holdings Value | Past Year Net Change | Change % | Valuation | Report Date |
|---|---|---|---|---|---|---|
| ESW Capital, LLC | 10%+ Owner | $8,314,476 | Mixed | 19 May 2021 | ||
| Mcdonald John T. | CEO, Director | $3,608,557 | -$34,064 | -0.94% | Mixed | 16 Mar 2026 |
| Rodney C. Favaron | President | $1,561,601 | Mixed | 16 Jun 2022 | ||
| Dan Doman | Chief Operating & Product Ofcr | $1,210,133 | Mixed | 16 Mar 2026 | ||
| ULYSSES AGGREGATOR, LP | 10%+ Owner | $1,160,461 | Mixed | 23 Aug 2022 | ||
| Oliver Robert MacFarlane Yates | Chief Sales Officer | $1,059,097 | Mixed | 16 Mar 2024 | ||
| Timothy Mattox | Director | $993,048 | Mixed | 27 Oct 2025 | ||
| Paul Kenneth Miller | Chief Operating Officer | $965,274 | Mixed | 16 Dec 2023 | ||
| Kinloch Gill III | CLO and Secretary | $897,060 | Mixed | 16 Sep 2023 | ||
| Michael Douglass Hill | CFO, Treasurer & Secretary | $723,556 | Mixed | 16 Mar 2026 | ||
| Matthew Breslin | Chief Revenue Officer | $691,500 | Mixed | 06 Feb 2024 | ||
| Karen Cummings | President and COO | $597,542 | Mixed | 30 Jun 2025 | ||
| Joe Ross | Director | $546,492 | Mixed | 31 Jul 2023 | ||
| Ian Burk | Chief Business Officer | $493,487 | Mixed | 16 Dec 2022 | ||
| David May | Director | $453,705 | Mixed | 27 Oct 2025 | ||
| Teresa Miles Walsh | Director | $342,441 | Mixed | 27 Oct 2025 | ||
| David H. S. Chung | Director | $295,027 | Mixed | 27 Oct 2025 | ||
| Stephen E. Courter | Director | $294,429 | Mixed | 27 Oct 2025 | ||
| Matthew Harnden Smith | General Counsel and Secretary | $242,710 | Mixed | 16 Jun 2025 |
Top shareholders of Upland Software, Inc. (13F + 13D/G + 3/4/5)
Grouped by holder across the latest SEC ownership disclosures. Ownership % is shown only when it is directly reported or safely comparable across share classes.
Methodology: rows are grouped by holder and ranked by the holder's primary source value. — indicates unavailable or non-comparable values; "mixed-class rows" means the latest filing spans non-comparable classes.
| Holder | Source | Role / Reporting | Ownership % | Shares | Holdings Value | 12M Net Δ | As of | Details |
|---|---|---|---|---|---|---|---|---|
| ESW Capital, LLC |
3/4/5
|
10%+ Owner |
—
class O/S missing
|
1,803,574
|
$8,314,476 | — | 19 May 2021 | |
| Petrus Paulus van Schaick |
13D/G
|
Jalak Investments B.V. |
9%
|
2,600,000
|
$6,162,000 | +$1,422,000 | 30 Sep 2025 | |
| Mcdonald John T. |
3/4/5
|
CEO, Director |
9.5%
|
2,754,625
|
$3,608,557 | -$34,064 | 16 Mar 2026 | |
| VANGUARD GROUP INC |
13F
|
Company |
6.3%
|
1,813,288
|
$2,593,002 | — | 31 Dec 2025 | |
| CastleKnight Master Fund LP |
13D/G
|
— |
3.7%
|
1,020,143
|
$2,458,545 | $0 | 31 Dec 2024 | |
| AMERIPRISE FINANCIAL INC |
13F
|
Company |
4.6%
|
1,340,193
|
$1,916,476 | — | 31 Dec 2025 | |
| ACADIAN ASSET MANAGEMENT LLC |
13F
|
Company |
4.4%
|
1,258,778
|
$1,798,000 | — | 31 Dec 2025 | |
| Rodney C. Favaron |
3/4/5
|
President |
—
class O/S missing
|
338,742
|
$1,561,601 | — | 16 Jun 2022 | |
| RICE HALL JAMES & ASSOCIATES, LLC |
13F
|
Company |
3.1%
|
893,697
|
$1,277,987 | — | 31 Dec 2025 | |
| NEW SOUTH CAPITAL MANAGEMENT INC |
13F
|
Company |
3.1%
|
887,094
|
$1,268,544 | — | 31 Dec 2025 | |
| D. E. Shaw & Co., Inc. |
13F
|
Company |
2.9%
|
848,388
|
$1,213,195 | — | 31 Dec 2025 | |
| Dan Doman |
3/4/5
|
Chief Operating & Product Ofcr |
3.2%
|
923,766
|
$1,210,133 | — | 16 Mar 2026 | |
| ULYSSES AGGREGATOR, LP |
3/4/5
|
10%+ Owner |
—
class O/S missing
|
251,727
|
$1,160,461 | — | 23 Aug 2022 | |
| CastleKnight Management LP |
13F
|
Company |
2.7%
|
777,201
|
$1,111,397 | — | 31 Dec 2025 | |
| Oliver Robert MacFarlane Yates |
3/4/5
|
Chief Sales Officer |
—
class O/S missing
|
251,567
|
$1,059,097 | — | 16 Mar 2024 | |
| Timothy Mattox |
3/4/5
|
Director |
1.5%
|
419,008
|
$993,048 | — | 27 Oct 2025 | |
| Paul Kenneth Miller |
3/4/5
|
Chief Operating Officer |
—
class O/S missing
|
209,387
|
$965,274 | — | 16 Dec 2023 | |
| Kinloch Gill III |
3/4/5
|
CLO and Secretary |
—
class O/S missing
|
194,590
|
$897,060 | — | 16 Sep 2023 | |
| BlackRock, Inc. |
13F
|
Company |
2.2%
|
621,236
|
$888,367 | — | 31 Dec 2025 | |
| Michael Douglass Hill |
3/4/5
|
CFO, Treasurer & Secretary |
1.9%
|
552,333
|
$723,556 | — | 16 Mar 2026 | |
| Matthew Breslin |
3/4/5
|
Chief Revenue Officer |
—
class O/S missing
|
150,000
|
$691,500 | — | 06 Feb 2024 | |
| MARSHALL WACE, LLP |
13F
|
Company |
1.6%
|
472,503
|
$675,680 | — | 31 Dec 2025 | |
| RBF Capital, LLC |
13F
|
Company |
1.5%
|
427,548
|
$611,394 | — | 31 Dec 2025 | |
| Karen Cummings |
3/4/5
|
President and COO |
1.1%
|
306,432
|
$597,542 | — | 30 Jun 2025 | |
| Joe Ross |
3/4/5
|
Director |
—
class O/S missing
|
118,545
|
$546,492 | — | 31 Jul 2023 | |
| Ian Burk |
3/4/5
|
Chief Business Officer |
—
class O/S missing
|
107,047
|
$493,487 | — | 16 Dec 2022 | |
| TWO SIGMA ADVISERS, LP |
13F
|
Company |
1.2%
|
335,300
|
$479,479 | — | 31 Dec 2025 | |
| David May |
3/4/5
|
Director |
0.66%
|
191,437
|
$453,705 | — | 27 Oct 2025 | |
| Assenagon Asset Management S.A. |
13F
|
Company |
1%
|
301,377
|
$430,969 | — | 31 Dec 2025 | |
| TWO SIGMA INVESTMENTS, LP |
13F
|
Company |
0.99%
|
286,989
|
$410,394 | — | 31 Dec 2025 | |
| GEODE CAPITAL MANAGEMENT, LLC |
13F
|
Company |
0.96%
|
278,139
|
$397,852 | — | 31 Dec 2025 | |
| PUBLIC EMPLOYEES RETIREMENT SYSTEM OF OHIO |
13F
|
Company |
0.96%
|
277,790
|
$397,240 | — | 31 Dec 2025 | |
| Russell Investments Group, Ltd. |
13F
|
Company |
0.91%
|
262,389
|
$375,213 | — | 31 Dec 2025 | |
| Man Group plc |
13F
|
Company |
0.9%
|
260,590
|
$372,644 | — | 31 Dec 2025 | |
| Teresa Miles Walsh |
3/4/5
|
Director |
0.5%
|
144,490
|
$342,441 | — | 27 Oct 2025 | |
| RENAISSANCE TECHNOLOGIES LLC |
13F
|
Company |
0.81%
|
234,091
|
$334,750 | — | 31 Dec 2025 | |
| David H. S. Chung |
3/4/5
|
Director |
0.43%
|
124,484
|
$295,027 | — | 27 Oct 2025 | |
| Stephen E. Courter |
3/4/5
|
Director |
0.43%
|
124,232
|
$294,429 | — | 27 Oct 2025 | |
| Matthew Harnden Smith |
3/4/5
|
General Counsel and Secretary |
0.46%
|
131,908
|
$242,710 | — | 16 Jun 2025 | |
| GSA CAPITAL PARTNERS LLP |
13F
|
Company |
0.56%
|
162,586
|
$232,000 | — | 31 Dec 2025 | |
| BRIDGEWAY CAPITAL MANAGEMENT, LLC |
13F
|
Company |
0.54%
|
155,600
|
$222,508 | — | 31 Dec 2025 | |
| Squarepoint Ops LLC |
13F
|
Company |
0.48%
|
139,197
|
$199,052 | — | 31 Dec 2025 | |
| STATE STREET CORP |
13F
|
Company |
0.38%
|
109,951
|
$157,230 | — | 31 Dec 2025 | |
| GOLDMAN SACHS GROUP INC |
13F
|
Company |
0.36%
|
103,825
|
$148,470 | — | 31 Dec 2025 | |
| Round Rock Advisors LLC |
13F
|
Company |
0.31%
|
90,331
|
$129,173 | — | 31 Dec 2025 | |
| Heron Bay Capital Management |
13F
|
Company |
0.29%
|
83,184
|
$118,953 | — | 31 Dec 2025 | |
| NORTHERN TRUST CORP |
13F
|
Company |
0.22%
|
64,044
|
$91,582 | — | 31 Dec 2025 | |
| EVERGREEN CAPITAL MANAGEMENT LLC |
13F
|
Company |
0.22%
|
62,390
|
$89,218 | — | 31 Dec 2025 | |
| UBS Group AG |
13F
|
Company |
0.17%
|
49,953
|
$71,433 | — | 31 Dec 2025 | |
| Boston Partners |
13F
|
Company |
0.16%
|
45,300
|
$64,780 | — | 31 Dec 2025 |
Recent Insider Transactions by Companies or Individuals for Upland Software, Inc.
Showing up to 300 most recent insider transactions from the last 12 months.
| Insider | Symbol | Class | Transaction | % | Value $ | * Price $ | Shares | Shares Owned | Date | Ownership |
|---|---|---|---|---|---|---|---|---|---|---|
| Mcdonald John T. | UPLD | Common Stock | Tax liability | -0.77% | -18,605 | 2,390,887 | 16 Mar 2026 | Direct | ||
| Michael Douglass Hill | UPLD | Common Stock | Tax liability | -2.23% | -8,931 | 392,291 | 16 Mar 2026 | Direct | ||
| Dan Doman | UPLD | Common Stock | Tax liability | -3.5% | -33,491 | 923,766 | 16 Mar 2026 | Direct | ||
| Dan Doman | UPLD | Common Stock | Award | 11.7% | 100,000 | 957,257 | 27 Feb 2026 | Direct | ||
| Michael Douglass Hill | UPLD | Common Stock | Award | 21.1% | 70,000 | 401,222 | 23 Feb 2026 | Direct | ||
| Dan Doman | UPLD | Common Stock | Award | 21.2% | 150,000 | 857,257 | 23 Feb 2026 | Direct | ||
| Dan Doman | UPLD | Common Stock | Tax liability | -3.36% | -24,595 | 707,257 | 16 Dec 2025 | Direct | ||
| Mcdonald John T. | UPLD | Common Stock | Tax liability | -0.81% | -19,677 | 2,409,492 | 16 Dec 2025 | Direct | ||
| Michael Douglass Hill | UPLD | Common Stock | Tax liability | -2.6% | -8,856 | 331,222 | 16 Dec 2025 | Direct | ||
| David H. S. Chung | UPLD | Common Stock | Award | 25.1% | 25,000 | 124,484 | 27 Oct 2025 | Direct | ||
| Stephen E. Courter | UPLD | Common Stock | Award | 25.2% | 25,000 | 124,232 | 27 Oct 2025 | Direct | ||
| Timothy Mattox | UPLD | Common Stock | Award | 6.35% | 25,000 | 419,008 | 27 Oct 2025 | Direct | ||
| David May | UPLD | Common Stock | Award | 15% | 25,000 | 191,437 | 27 Oct 2025 | Direct | ||
| Teresa Miles Walsh | UPLD | Common Stock | Award | 20.9% | 25,000 | 144,490 | 27 Oct 2025 | Direct | ||
| Mcdonald John T. | UPLD | Common Stock | Tax liability | -0.94% | -22,956 | 2,429,169 | 16 Sep 2025 | Direct | ||
| Michael Douglass Hill | UPLD | Common Stock | Tax liability | -3.18% | -11,152 | 340,078 | 16 Sep 2025 | Direct | ||
| Dan Doman | UPLD | Common Stock | Tax liability | -3.46% | -26,236 | 731,852 | 16 Sep 2025 | Direct | ||
| Mcdonald John T. | UPLD | Common Stock | Sale | -0.59% | $34,064 | $2.36 | -14,438 | 2,452,125 | 11 Sep 2025 | Direct |
| Karen Cummings | UPLD | Common Stock | Tax liability | -11.8% | -40,993 | 306,432 | 30 Jun 2025 | Direct | ||
| Matthew Harnden Smith | UPLD | Common Stock | Tax liability | -2.65% | -3,596 | 131,908 | 16 Jun 2025 | Direct | ||
| Mcdonald John T. | UPLD | Common Stock | Tax liability | -0.92% | -22,957 | 2,466,563 | 16 Jun 2025 | Direct | ||
| Michael Douglass Hill | UPLD | Common Stock | Tax liability | -3.08% | -11,152 | 351,230 | 16 Jun 2025 | Direct | ||
| Dan Doman | UPLD | Common Stock | Tax liability | -1.91% | -14,758 | 758,088 | 16 Jun 2025 | Direct | ||
| Karen Cummings | UPLD | Common Stock | Tax liability | -3.2% | -11,479 | 347,425 | 16 Jun 2025 | Direct | ||
| Dan Doman | UPLD | Common Stock | Award | 82.8% | 350,000 | 772,846 | 13 Jun 2025 | Direct |
* An asterisk sign (*) next to the price indicates that the price is likely invalid.