Upland Software, Inc. ($UPLD) Insider Transactions

Last updated: 2026-03-17 21:01 UTC | Total transactions: 136

In the last 12 months, insiders at Upland Software, Inc. ($UPLD) filed 136 transactions with the SEC: 4 open-market purchases totaling $292,435 and 7 sales totaling $318,739. Net insider sentiment: net selling.

Upland Software, Inc. operates in the Services-prepackaged software industry (Technology sector).

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Recent Insider Transactions

Transaction Date Insider Name Title Transaction Type Security Shares Price Shares Owned Following Total Shares Outstanding % of Owned % of Outstanding
March 16, 2026 Doman Dan Chief Operating & Product Ofcr F Common Stock 33491 $0.54 923,766.0000 28,891,348 3.50% 0.12%
March 16, 2026 Hill Michael Douglass CFO, Treasurer & Secretary F Common Stock 8931 $0.54 552,333.0000 28,891,348 1.59% 0.03%
March 16, 2026 MCDONALD JOHN T CEO F Common Stock 18605 $0.54 2,754,625.0000 28,891,348 0.67% 0.06%
Feb. 27, 2026 Doman Dan Chief Operating & Product Ofcr A Common Stock 100000 $0.00 957,257.0000 28,891,348 11.67% 0.35%
Feb. 23, 2026 Hill Michael Douglass CFO, Treasurer & Secretary A Common Stock 70000 $0.00 561,264.0000 28,891,348 14.25% 0.24%
Feb. 23, 2026 Doman Dan Chief Operating & Product Ofcr A Common Stock 150000 $0.00 857,257.0000 28,891,348 21.21% 0.52%
Dec. 16, 2025 Hill Michael Douglass CFO, Treasurer & Secretary F Common Stock 8856 $1.49 491,264.0000 28,891,348 1.77% 0.03%
Dec. 16, 2025 MCDONALD JOHN T CEO F Common Stock 19677 $1.49 2,773,230.0000 28,891,348 0.70% 0.07%
Dec. 16, 2025 Doman Dan Chief Operating & Product Ofcr F Common Stock 24595 $1.49 707,257.0000 28,891,348 3.36% 0.09%
Oct. 27, 2025 Mattox Timothy Director A Common Stock 25000 $0.00 419,008.0000 28,891,348 6.35% 0.09%
Oct. 27, 2025 MAY DAVID Director A Common Stock 25000 $0.00 191,437.0000 28,891,348 15.02% 0.09%
Oct. 27, 2025 Walsh Teresa Miles Director A Common Stock 25000 $0.00 144,490.0000 28,891,348 20.92% 0.09%
Oct. 27, 2025 Chung David H S Director A Common Stock 25000 $0.00 124,484.0000 28,891,348 25.13% 0.09%
Oct. 27, 2025 COURTER STEPHEN E Director A Common Stock 25000 $0.00 124,232.0000 28,891,348 25.19% 0.09%
Sept. 16, 2025 Doman Dan Chief Operating & Product Ofcr F Common Stock 26236 $2.48 731,852.0000 28,708,922 3.46% 0.09%
Sept. 16, 2025 MCDONALD JOHN T CEO F Common Stock 22956 $2.48 2,792,907.0000 28,708,922 0.82% 0.08%
Sept. 16, 2025 Hill Michael Douglass CFO, Treasurer & Secretary F Common Stock 11152 $2.48 500,120.0000 28,708,922 2.18% 0.04%
Sept. 11, 2025 MCDONALD JOHN T CEO S Common Stock 14438 $2.36 2,815,863.0000 28,708,922 0.51% 0.05%
June 30, 2025 Cummings Karen President and COO F Common Stock 40993 $1.95 306,432.0000 28,168,267 11.80% 0.15%
June 13, 2025 Doman Dan Chief Product Officer A Common Stock 350000 $0.00 772,846.0000 28,168,267 82.77% 1.24%
June 16, 2025 MCDONALD JOHN T CEO F Common Stock 22957 $1.84 2,830,301.0000 28,168,267 0.80% 0.08%
June 16, 2025 Hill Michael Douglass CFO & Treasurer F Common Stock 11152 $1.84 511,272.0000 28,168,267 2.13% 0.04%
June 16, 2025 Doman Dan Chief Product Officer F Common Stock 14758 $1.84 758,088.0000 28,168,267 1.91% 0.05%
June 16, 2025 Cummings Karen President and COO F Common Stock 11479 $1.84 347,425.0000 28,168,267 3.20% 0.04%
June 16, 2025 Smith Matthew Harnden General Counsel and Secretary F Common Stock 3596 $1.84 131,908.0000 28,168,267 2.65% 0.01%
March 16, 2025 Cummings Karen President and COO F Common Stock 8648 $3.10 358,904.0000 28,168,267 2.35% 0.03%
March 17, 2025 Mattox Timothy Director S Common Stock 20000 $3.19 394,008.0000 28,168,267 4.83% 0.07%
March 16, 2025 Smith Matthew Harnden General Counsel and Secretary F Common Stock 4135 $3.10 135,504.0000 28,168,267 2.96% 0.01%
March 16, 2025 MCDONALD JOHN T CEO F Common Stock 24273 $3.10 2,853,258.0000 28,168,267 0.84% 0.09%
March 16, 2025 Hill Michael Douglass CFO & Treasurer F Common Stock 12653 $3.10 522,424.0000 28,168,267 2.36% 0.04%
March 16, 2025 Doman Dan Chief Product Officer F Common Stock 16414 $3.10 422,846.0000 28,168,267 3.74% 0.06%
Jan. 28, 2025 Hill Michael Douglass CFO & Treasurer A Common Stock 70000 $0.00 535,077.0000 28,168,267 15.05% 0.25%
Jan. 28, 2025 Smith Matthew Harnden General Counsel and Secretary A Common Stock 50000 $0.00 139,639.0000 28,168,267 55.78% 0.18%
Jan. 28, 2025 MCDONALD JOHN T CEO A Common Stock 250000 $0.00 2,877,531.0000 28,168,267 9.51% 0.89%
Jan. 28, 2025 MCDONALD JOHN T CEO A Performance Share Unit 250000 $0.00 250,000.0000 28,168,267 9999.99% 0.89%
Jan. 28, 2025 Doman Dan Chief Product Officer A Common Stock 150000 $0.00 439,260.0000 28,168,267 51.86% 0.53%
Dec. 16, 2024 Doman Dan Chief Product Officer F Common Stock 11643 $4.51 289,260.0000 27,440,968 3.87% 0.04%
Dec. 16, 2024 Cummings Karen President and COO F Common Stock 7812 $4.51 367,552.0000 27,440,968 2.08% 0.03%
Dec. 16, 2024 MCDONALD JOHN T CEO F Common Stock 17833 $4.51 2,627,531.0000 27,440,968 0.67% 0.06%
Dec. 16, 2024 Smith Matthew Harnden General Counsel and Secretary F Common Stock 6197 $4.51 89,639.0000 27,440,968 6.47% 0.02%
Dec. 17, 2024 Mattox Timothy Director S Common Stock 2768 $4.56 414,008.0000 27,440,968 0.66% 0.01%
Dec. 16, 2024 Hill Michael Douglass CFO & Treasurer F Common Stock 11070 $4.51 465,077.0000 27,440,968 2.32% 0.04%
Dec. 10, 2024 MCDONALD JOHN T CEO M Common Stock 187500 $0.00 2,719,145.0000 27,440,968 7.41% 0.68%
Dec. 10, 2024 MCDONALD JOHN T CEO M Performance Share Unit 187500 $0.00 0.0000 27,440,968 100.00% 0.68%
Dec. 9, 2024 MCDONALD JOHN T CEO M Performance Share Unit 125000 $0.00 187,500.0000 27,440,968 40.00% 0.46%
Dec. 6, 2024 MCDONALD JOHN T CEO M Performance Share Unit 187500 $0.00 312,500.0000 27,440,968 37.50% 0.68%
Dec. 10, 2024 MCDONALD JOHN T CEO F Common Stock 73781 $5.31 2,645,364.0000 27,440,968 2.71% 0.27%
Dec. 9, 2024 MCDONALD JOHN T CEO M Common Stock 125000 $0.00 2,580,833.0000 27,440,968 5.09% 0.46%
Dec. 6, 2024 MCDONALD JOHN T CEO F Common Stock 73781 $4.45 2,455,833.0000 27,440,968 2.92% 0.27%
Dec. 6, 2024 MCDONALD JOHN T CEO M Common Stock 187500 $0.00 2,529,614.0000 27,440,968 8.01% 0.68%
Dec. 9, 2024 MCDONALD JOHN T CEO F Common Stock 49188 $4.89 2,531,645.0000 27,440,968 1.91% 0.18%
Dec. 5, 2024 MCDONALD JOHN T CEO F Common Stock 24594 $4.32 2,342,114.0000 27,440,968 1.04% 0.09%
Dec. 4, 2024 MCDONALD JOHN T CEO M Performance Share Unit 31250 $0.00 562,500.0000 27,440,968 5.26% 0.11%
Dec. 5, 2024 MCDONALD JOHN T CEO M Performance Share Unit 62500 $0.00 500,000.0000 27,440,968 11.11% 0.23%
Dec. 3, 2024 MCDONALD JOHN T CEO F Common Stock 61484 $4.37 2,285,255.0000 27,440,968 2.62% 0.22%
Dec. 3, 2024 MCDONALD JOHN T CEO M Common Stock 156250 $0.00 2,346,739.0000 27,440,968 7.13% 0.57%
Dec. 5, 2024 MCDONALD JOHN T CEO M Common Stock 62500 $0.00 2,366,708.0000 27,440,968 2.71% 0.23%
Dec. 3, 2024 MCDONALD JOHN T CEO M Performance Share Unit 156250 $0.00 593,750.0000 27,440,968 20.83% 0.57%
Dec. 4, 2024 MCDONALD JOHN T CEO M Common Stock 31250 $0.00 2,316,505.0000 27,440,968 1.37% 0.11%
Dec. 4, 2024 MCDONALD JOHN T CEO F Common Stock 12297 $4.00 2,304,208.0000 27,440,968 0.53% 0.04%
Nov. 14, 2024 Mattox Timothy Director S Common Stock 18000 $2.50 416,776.0000 27,440,968 4.14% 0.07%
Nov. 13, 2024 Mattox Timothy Director S Common Stock 2000 $2.64 434,776.0000 27,440,968 0.46% 0.01%
Nov. 4, 2024 MAY DAVID Director A Common Stock 25000 $0.00 166,437.0000 27,440,968 17.68% 0.09%
Nov. 4, 2024 Chung David H S Director A Common Stock 25000 $0.00 99,484.0000 27,440,968 33.56% 0.09%
Nov. 4, 2024 COURTER STEPHEN E Director A Common Stock 25000 $0.00 99,232.0000 27,440,968 33.68% 0.09%
Nov. 4, 2024 Mattox Timothy Director A Common Stock 25000 $0.00 436,776.0000 27,440,968 6.07% 0.09%
Nov. 4, 2024 Walsh Teresa Miles Director A Common Stock 25000 $0.00 119,490.0000 27,440,968 26.46% 0.09%
Sept. 16, 2024 Doman Dan Chief Product Officer F Common Stock 11643 $2.24 300,903.0000 27,265,746 3.73% 0.04%
Sept. 16, 2024 Hill Michael Douglass CFO & Treasurer F Common Stock 11070 $2.24 476,147.0000 27,265,746 2.27% 0.04%
Sept. 16, 2024 Cummings Karen President and COO F Common Stock 7815 $2.24 375,364.0000 27,265,746 2.04% 0.03%
Sept. 16, 2024 MCDONALD JOHN T CEO F Common Stock 17833 $2.24 2,190,489.0000 27,265,746 0.81% 0.07%
Sept. 16, 2024 Smith Matthew Harnden General Counsel and Secretary F Common Stock 1240 $2.24 95,836.0000 27,265,746 1.28% 0.00%
Aug. 8, 2024 MCDONALD JOHN T CEO P Common Stock 33635 $1.98 2,141,957.0000 27,265,746 1.60% 0.12%
Aug. 9, 2024 MCDONALD JOHN T CEO P Common Stock 66365 $1.96 2,208,322.0000 27,265,746 3.10% 0.24%
June 16, 2024 MCDONALD JOHN T CEO F Common Stock 17834 $2.63 2,108,322.0000 29,908,407 0.84% 0.06%
June 16, 2024 Hill Michael Douglass CFO & Treasurer F Common Stock 11070 $2.63 487,217.0000 29,908,407 2.22% 0.04%
June 16, 2024 Cummings Karen President and COO F Common Stock 7815 $2.63 383,179.0000 29,908,407 2.00% 0.03%
June 16, 2024 Smith Matthew Harnden General Counsel and Secretary F Common Stock 1460 $2.63 97,076.0000 29,908,407 1.48% 0.00%
June 16, 2024 Doman Dan Chief Product Officer F Common Stock 13447 $2.63 312,566.0000 29,908,407 4.12% 0.04%
June 5, 2024 MCDONALD JOHN T CEO A Performance Share Unit 500000 $0.00 750,000.0000 29,908,407 200.00% 1.67%
March 16, 2024 Smith Matthew Harnden General Counsel and Secretary F Common Stock 1464 $4.21 98,536.0000 29,908,407 1.46% 0.00%
March 16, 2024 Doman Dan Chief Product Officer F Common Stock 15258 $4.21 326,013.0000 29,908,407 4.47% 0.05%
March 16, 2024 Cummings Karen President and COO F Common Stock 9515 $4.21 390,994.0000 29,908,407 2.38% 0.03%
March 16, 2024 Yates Oliver Robert MacFarlane Chief Sales Officer F Common Stock 6672 $4.21 251,567.0000 29,908,407 2.58% 0.02%
March 16, 2024 Hill Michael Douglass CFO & Treasurer F Common Stock 12559 $4.21 498,287.0000 29,908,407 2.46% 0.04%
March 16, 2024 MCDONALD JOHN T CEO F Common Stock 19330 $4.21 2,126,156.0000 29,908,407 0.90% 0.06%
Jan. 29, 2024 MCDONALD JOHN T CEO A Performance Share Unit 250000 $0.00 250,000.0000 29,908,407 9999.99% 0.84%
Jan. 29, 2024 MCDONALD JOHN T CEO A Common Stock 250000 $0.00 2,145,486.0000 29,908,407 13.19% 0.84%
Feb. 6, 2024 Breslin Matthew Chief Revenue Officer A Common Stock 150000 $0.00 150,000.0000 29,908,407 9999.99% 0.50%
Jan. 29, 2024 MCDONALD JOHN T CEO A Performance Share Unit 250000 $0.00 250,000.0000 29,908,407 9999.99% 0.84%
Jan. 29, 2024 Yates Oliver Robert MacFarlane Chief Sales Officer A Common Stock 135000 $0.00 258,239.0000 29,908,407 109.54% 0.45%
Jan. 29, 2024 Hill Michael Douglass CFO & Treasurer A Common Stock 100000 $0.00 510,846.0000 29,908,407 24.34% 0.33%
Jan. 29, 2024 Smith Matthew Harnden General Counsel and Secretary A Common Stock 50000 $0.00 100,000.0000 29,908,407 100.00% 0.17%
Jan. 29, 2024 Doman Dan Chief Product Officer A Common Stock 150000 $0.00 341,271.0000 29,908,407 78.42% 0.50%
Jan. 29, 2024 Cummings Karen Executive VP & Senior GM A Common Stock 150000 $0.00 400,509.0000 29,908,407 59.88% 0.50%
Jan. 29, 2024 MCDONALD JOHN T CEO A Common Stock 250000 $0.00 2,145,486.0000 29,908,407 13.19% 0.84%
Jan. 6, 2024 Mattox Timothy Director A Common Stock 27687 $0.00 411,776.0000 29,908,407 7.21% 0.09%
Dec. 16, 2023 Hill Michael Douglass CFO & Treasurer F Common Stock 10004 $4.61 410,846.0000 32,221,855 2.38% 0.03%
Dec. 16, 2023 Cummings Karen Executive VP & Senior GM F Common Stock 5279 $4.61 250,509.0000 32,221,855 2.06% 0.02%
Dec. 16, 2023 Yates Oliver Robert MacFarlane Chief Sales Officer F Common Stock 2740 $4.61 123,239.0000 32,221,855 2.17% 0.01%
Dec. 16, 2023 MCDONALD JOHN T CEO F Common Stock 11650 $4.61 1,895,486.0000 32,221,855 0.61% 0.04%
Dec. 16, 2023 Miller Paul Kenneth Chief Operating Officer F Common Stock 6561 $4.61 209,387.0000 32,221,855 3.04% 0.02%
Dec. 16, 2023 Doman Dan Chief Product Officer F Common Stock 8528 $4.61 191,271.0000 32,221,855 4.27% 0.03%
Nov. 21, 2023 COURTER STEPHEN E Director S Common Stock 20448 $4.43 74,232.0000 32,221,855 21.60% 0.06%
Nov. 7, 2023 Doman Dan Chief Product Officer S Common Stock 13996 $4.80 199,779.0000 32,221,855 6.55% 0.04%
Oct. 31, 2023 Smith Matthew Harnden General Counsel and Secretary A Common Stock 50000 $0.00 50,000.0000 32,221,855 9999.99% 0.16%
Sept. 16, 2023 Cummings Karen Executive VP & Senior GM F Common Stock 8323 $3.86 255,788.0000 32,221,855 3.15% 0.03%
Sept. 16, 2023 MCDONALD JOHN T CEO F Common Stock 11650 $3.86 1,907,136.0000 32,221,855 0.61% 0.04%
Sept. 16, 2023 Miller Paul Kenneth Chief Operating Officer F Common Stock 6561 $3.86 215,948.0000 32,221,855 2.95% 0.02%
Sept. 16, 2023 Doman Dan Chief Product Officer F Common Stock 8528 $3.86 213,775.0000 32,221,855 3.84% 0.03%
Sept. 16, 2023 Gill Kinloch III CLO and Secretary F Common Stock 6724 $3.86 194,590.0000 32,221,855 3.34% 0.02%
Sept. 16, 2023 Hill Michael Douglass CFO & Treasurer F Common Stock 10004 $3.86 420,850.0000 32,221,855 2.32% 0.03%
Sept. 16, 2023 Yates Oliver Robert MacFarlane Chief Sales Officer F Common Stock 2740 $3.86 125,979.0000 32,221,855 2.13% 0.01%
July 31, 2023 COURTER STEPHEN E Director A Common Stock 62816 $0.00 94,680.0000 32,221,855 197.14% 0.19%
July 31, 2023 MAY DAVID Director A Common Stock 62816 $0.00 141,437.0000 32,221,855 79.90% 0.19%
July 31, 2023 Chung David H S Director A Common Stock 62816 $0.00 74,484.0000 32,221,855 538.36% 0.19%
July 31, 2023 Walsh Teresa Miles Director A Common Stock 62816 $0.00 94,490.0000 32,221,855 198.32% 0.19%
July 31, 2023 Ross Joe Director A Common Stock 62816 $0.00 118,545.0000 32,221,855 112.72% 0.19%
June 16, 2023 Miller Paul Kenneth Chief Operating Officer F Common Stock 6561 $3.53 222,509.0000 32,221,855 2.86% 0.02%
June 16, 2023 MCDONALD JOHN T CEO F Common Stock 11650 $3.53 1,918,786.0000 32,221,855 0.60% 0.04%
June 16, 2023 Gill Kinloch III CLO F Common Stock 6724 $3.53 201,314.0000 32,221,855 3.23% 0.02%
June 16, 2023 Doman Dan Chief Product Officer F Common Stock 8528 $3.53 222,303.0000 32,221,855 3.69% 0.03%
June 16, 2023 Hill Michael Douglass CFO F Common Stock 10004 $3.53 430,854.0000 32,221,855 2.27% 0.03%
March 16, 2023 Doman Dan Chief Product Officer F Common Stock 10407 $4.72 230,831.0000 32,221,855 4.31% 0.03%
March 16, 2023 MCDONALD JOHN T CEO F Common Stock 12704 $4.72 1,930,436.0000 32,221,855 0.65% 0.04%
March 16, 2023 Miller Paul Kenneth Chief Operating Officer F Common Stock 7864 $4.72 229,070.0000 32,221,855 3.32% 0.02%
March 16, 2023 Hill Michael Douglass CFO & Treasurer F Common Stock 11054 $4.72 440,858.0000 32,221,855 2.45% 0.03%
March 16, 2023 Gill Kinloch III CLO and Secretary F Common Stock 7629 $4.72 208,038.0000 32,221,855 3.54% 0.02%
March 10, 2023 MCDONALD JOHN T CEO P Common Stock 10000 $4.80 1,933,140.0000 32,221,855 0.52% 0.03%
March 13, 2023 MCDONALD JOHN T CEO P Common Stock 10000 $4.75 1,943,140.0000 32,221,855 0.52% 0.03%
Feb. 21, 2023 Hill Michael Douglass CFO & Treasurer A Common Stock 100000 $0.00 451,912.0000 32,221,855 28.42% 0.31%
Feb. 21, 2023 MCDONALD JOHN T CEO A Performance Share Unit 100000 $0.00 193,750.0000 32,221,855 106.67% 0.31%
Feb. 21, 2023 Gill Kinloch III CLO and Secretary A Common Stock 100000 $0.00 215,667.0000 32,221,855 86.46% 0.31%
Feb. 21, 2023 Miller Paul Kenneth Chief Operating Officer A Common Stock 100000 $0.00 236,934.0000 32,221,855 73.03% 0.31%
Feb. 21, 2023 Doman Dan Chief Product Officer A Common Stock 100000 $0.00 241,238.0000 32,221,855 70.80% 0.31%
Feb. 21, 2023 MCDONALD JOHN T CEO A Common Stock 100000 $0.00 1,923,140.0000 32,221,855 5.49% 0.31%