Insider Transactions Reported by 19 Insiders of Upland Software, Inc.

Symbol
UPLD on Nasdaq
Location
Austin, TX

Insiders trading volume in the past year

Upland Software, Inc. executives and other stock owners filed with the SEC include:

Name Relationship Holdings Value Past Year Net Change Change % Report Date
ESW Capital, LLC 10%+ Owner $8,314,476 19 May 2021
MCDONALD JOHN T. CEO, Director $5,579,279 -$34,064 -0.61% 16 Dec 2025
Rodney C. Favaron President $1,561,601 16 Jun 2022
Dan Doman Chief Operating & Product Ofcr $1,254,006 27 Feb 2026
ULYSSES AGGREGATOR, LP 10%+ Owner $1,160,461 23 Aug 2022
Oliver Robert MacFarlane Yates Chief Sales Officer $1,059,097 16 Mar 2024
Timothy Mattox Director $993,048 -$63,862 -6% 27 Oct 2025
Paul Kenneth Miller Chief Operating Officer $965,274 16 Dec 2023
Kinloch Gill III CLO and Secretary $897,060 16 Sep 2023
Michael Douglass Hill CFO, Treasurer & Secretary $802,607 23 Feb 2026
Matthew Breslin Chief Revenue Officer $691,500 06 Feb 2024
Karen Cummings President and COO $597,542 30 Jun 2025
Joe Ross Director $546,492 31 Jul 2023
Ian Burk Chief Business Officer $493,487 16 Dec 2022
DAVID MAY Director $453,705 27 Oct 2025
Teresa Miles Walsh Director $342,441 27 Oct 2025
David H. S. Chung Director $295,027 27 Oct 2025
STEPHEN E. COURTER Director $294,429 27 Oct 2025
Matthew Harnden Smith General Counsel and Secretary $242,710 16 Jun 2025

Recent Insider Transactions by Companies or Individuals for Upland Software, Inc.

Insider Symbol Class Transaction % Value $ * Price $ Shares Shares Owned Date Ownership
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
Timothy Mattox UPLD Common Stock Sale -4.83% $63,862 $3.19 -20,000 394,008 17 Mar 2025 Direct
Matthew Harnden Smith UPLD Common Stock Tax liability -2.96% -4,135 135,504 16 Mar 2025 Direct
MCDONALD JOHN T. UPLD Common Stock Tax liability -0.97% -24,273 2,489,520 16 Mar 2025 Direct
Michael Douglass Hill UPLD Common Stock Tax liability -3.37% -12,653 362,382 16 Mar 2025 Direct
Dan Doman UPLD Common Stock Tax liability -3.74% -16,414 422,846 16 Mar 2025 Direct
Karen Cummings UPLD Common Stock Tax liability -2.35% -8,648 358,904 16 Mar 2025 Direct
Matthew Harnden Smith UPLD Common Stock Award 55.8% 50,000 139,639 28 Jan 2025 Direct
MCDONALD JOHN T. UPLD Common Stock Award 11% 250,000 2,513,793 28 Jan 2025 Direct
MCDONALD JOHN T. UPLD Performance Share Unit Award 250,000 250,000 28 Jan 2025 Direct
Michael Douglass Hill UPLD Common Stock Award 23% 70,000 375,035 28 Jan 2025 Direct
Dan Doman UPLD Common Stock Award 51.9% 150,000 439,260 28 Jan 2025 Direct
Timothy Mattox UPLD Common Stock Sale -0.66% $12,612 $4.56 -2,768 414,008 17 Dec 2024 Direct
Matthew Harnden Smith UPLD Common Stock Tax liability -6.47% -6,197 89,639 16 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Tax liability -0.78% -17,833 2,263,793 16 Dec 2024 Direct
Michael Douglass Hill UPLD Common Stock Tax liability -3.5% -11,070 305,035 16 Dec 2024 Direct
Dan Doman UPLD Common Stock Tax liability -3.87% -11,643 289,260 16 Dec 2024 Direct
Karen Cummings UPLD Common Stock Tax liability -2.08% -7,812 367,552 16 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Tax liability -3.13% -73,781 2,281,626 10 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Options Exercise 8.65% 187,500 2,355,407 10 Dec 2024 Direct
MCDONALD JOHN T. UPLD Performance Share Unit Options Exercise -100% -187,500 0 10 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Tax liability -2.22% -49,188 2,167,907 09 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Options Exercise 5.97% 125,000 2,217,095 09 Dec 2024 Direct
MCDONALD JOHN T. UPLD Performance Share Unit Options Exercise -40% -125,000 187,500 09 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Tax liability -3.41% -73,781 2,092,095 06 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Options Exercise 9.48% 187,500 2,165,876 06 Dec 2024 Direct
MCDONALD JOHN T. UPLD Performance Share Unit Options Exercise -37.5% -187,500 312,500 06 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Tax liability -1.23% -24,594 1,978,376 05 Dec 2024 Direct
MCDONALD JOHN T. UPLD Common Stock Options Exercise 3.22% 62,500 2,002,970 05 Dec 2024 Direct
* An asterisk sign (*) next to the price indicates that the price is likely invalid.