Upland Software, Inc. (UPLD)

Latest Insider Confidence Score

2026Q1

49.8
Bearish

Company insider confidence (by quarter)

2014Q4 2026Q1

Largest shareholders

Insider Role (last 12 mo) Shares held Filed at
Wave Systems Corp 10% Owner 2,803,574 Dec 18, 2017
ESW Capital, LLC 10% Owner 1,803,574 May 24, 2021
Liemandt Joseph 10% Owner 1,803,574 May 24, 2021
DevFactory FZ-LLC — 1,803,574 May 24, 2021
EPM Live, Inc. Other 1,803,574 Aug 28, 2018

Recent buy/sell transactions

Exec date Filing date Insider Role Signal Confidence Shares % of shares Under plan? Amount (USD)
Feb 27, 2026 Mar 3, 2026 Doman Dan COO Neutral 90.0 +100,000 11.67% ✗ -
Feb 23, 2026 Feb 25, 2026 Hill Michael Douglass CFO Neutral 90.0 +70,000 14.25% ✗ -
Feb 23, 2026 Feb 25, 2026 Doman Dan COO Neutral 90.0 +150,000 21.21% ✗ -
Dec 16, 2025 Dec 17, 2025 Doman Dan COO Sell 46.3 -24,595 -3.36% ✗ $36.5K
Dec 16, 2025 Dec 17, 2025 MCDONALD JOHN T CEO Sell 48.8 -19,677 -0.70% ✗ $29.2K
Dec 16, 2025 Dec 17, 2025 Hill Michael Douglass CFO Sell 46.3 -8,856 -1.77% ✗ $13.2K
Oct 27, 2025 Oct 29, 2025 Chung David H S Director Neutral 90.0 +25,000 25.13% ✗ -
Oct 27, 2025 Oct 29, 2025 COURTER STEPHEN E Director Neutral 90.0 +25,000 25.19% ✗ -
Oct 27, 2025 Oct 29, 2025 Mattox Timothy Director Neutral 85.0 +25,000 6.35% ✗ -
Oct 27, 2025 Oct 29, 2025 MAY DAVID Director Neutral 90.0 +25,000 15.02% ✗ -
Oct 27, 2025 Oct 29, 2025 Walsh Teresa Miles Director Neutral 90.0 +25,000 20.92% ✗ -
Sep 16, 2025 Sep 17, 2025 MCDONALD JOHN T CEO Sell 45.0 -22,956 -0.82% ✗ $56.9K
Sep 16, 2025 Sep 17, 2025 Hill Michael Douglass CFO Sell 46.3 -11,152 -2.18% ✗ $27.7K
Sep 16, 2025 Sep 17, 2025 Doman Dan COO Sell 42.5 -26,236 -3.46% ✗ $65.1K
Sep 11, 2025 Sep 11, 2025 MCDONALD JOHN T CEO Sell 36.3 -14,438 -0.51% ✗ $34.1K
Jun 30, 2025 Jul 1, 2025 Cummings Karen COO Sell 42.5 -40,993 -11.80% ✗ $79.9K
Jun 16, 2025 Jun 17, 2025 Smith Matthew Harnden General Counsel and Secretary Sell 47.5 -3,596 -2.65% ✗ $6.6K
Jun 16, 2025 Jun 17, 2025 MCDONALD JOHN T CEO Sell 48.8 -22,957 -0.80% ✗ $42.2K
Jun 16, 2025 Jun 17, 2025 Hill Michael Douglass CFO Sell 46.3 -11,152 -2.13% ✗ $20.5K
Jun 13, 2025 Jun 17, 2025 Doman Dan Chief Product Officer Sell 91.3 +335,242 79.28% ✗ $27.2K
Jun 16, 2025 Jun 17, 2025 Cummings Karen COO Sell 46.3 -11,479 -3.20% ✗ $21.1K
Mar 17, 2025 Mar 17, 2025 Mattox Timothy Director Sell 37.5 -20,000 -4.83% ✓ $63.9K
Mar 16, 2025 Mar 17, 2025 Smith Matthew Harnden General Counsel and Secretary Sell 46.3 -4,135 -2.96% ✗ $12.8K
Mar 16, 2025 Mar 17, 2025 MCDONALD JOHN T CEO Sell 45.0 -24,273 -0.84% ✗ $75.2K
Mar 16, 2025 Mar 17, 2025 Hill Michael Douglass CFO Sell 46.3 -12,653 -2.36% ✗ $39.2K
Mar 16, 2025 Mar 17, 2025 Doman Dan Chief Product Officer Sell 42.5 -16,414 -3.74% ✗ $50.9K
Mar 16, 2025 Mar 17, 2025 Cummings Karen COO Sell 46.3 -8,648 -2.35% ✗ $26.8K
Jan 28, 2025 Jan 30, 2025 Smith Matthew Harnden General Counsel and Secretary Neutral 90.0 +50,000 55.78% ✗ -
Jan 28, 2025 Jan 30, 2025 MCDONALD JOHN T CEO Neutral 85.0 +250,000 9.51% ✗ -
Jan 28, 2025 Jan 30, 2025 Hill Michael Douglass CFO Neutral 90.0 +70,000 15.05% ✗ -
Jan 28, 2025 Jan 30, 2025 Doman Dan Chief Product Officer Neutral 90.0 +150,000 51.86% ✗ -
Dec 17, 2024 Dec 17, 2024 Mattox Timothy Director Sell 51.3 -2,768 -0.66% ✓ $12.6K
Dec 16, 2024 Dec 17, 2024 Smith Matthew Harnden General Counsel and Secretary Sell 46.3 -6,197 -6.47% ✗ $27.9K
Dec 16, 2024 Dec 17, 2024 MCDONALD JOHN T CEO Sell 45.0 -17,833 -0.67% ✗ $80.4K
Dec 16, 2024 Dec 17, 2024 Hill Michael Douglass CFO Sell 46.3 -11,070 -2.32% ✗ $49.9K
Dec 16, 2024 Dec 17, 2024 Doman Dan Chief Product Officer Sell 42.5 -11,643 -3.87% ✗ $52.5K
Dec 16, 2024 Dec 17, 2024 Cummings Karen COO Sell 46.3 -7,812 -2.08% ✗ $35.2K
Dec 6, 2024 Dec 10, 2024 MCDONALD JOHN T CEO Sell 40.0 -196,750 -2.77% ✗ $960.6K
Dec 3, 2024 Dec 5, 2024 MCDONALD JOHN T CEO Sell 40.0 -98,375 -1.56% ✗ $424.1K
Nov 13, 2024 Nov 15, 2024 Mattox Timothy Director Sell 22.5 -20,000 -4.58% ✗ $50.3K
Nov 4, 2024 Nov 4, 2024 Chung David H S Director Neutral 90.0 +25,000 33.56% ✗ -
Nov 4, 2024 Nov 4, 2024 COURTER STEPHEN E Director Neutral 90.0 +25,000 33.68% ✗ -
Nov 4, 2024 Nov 4, 2024 Mattox Timothy Director Neutral 85.0 +25,000 6.07% ✗ -
Nov 4, 2024 Nov 4, 2024 Walsh Teresa Miles Director Neutral 90.0 +25,000 26.46% ✗ -
Nov 4, 2024 Nov 4, 2024 MAY DAVID Director Neutral 90.0 +25,000 17.68% ✗ -
Sep 16, 2024 Sep 17, 2024 Smith Matthew Harnden General Counsel and Secretary Sell 47.5 -1,240 -1.28% ✗ $2.8K
Sep 16, 2024 Sep 17, 2024 MCDONALD JOHN T CEO Sell 48.8 -17,833 -0.81% ✗ $39.9K
Sep 16, 2024 Sep 17, 2024 Cummings Karen COO Sell 46.3 -7,815 -2.04% ✗ $17.5K
Sep 16, 2024 Sep 17, 2024 Doman Dan Chief Product Officer Sell 46.3 -11,643 -3.73% ✗ $26.1K
Sep 16, 2024 Sep 17, 2024 Hill Michael Douglass CFO Sell 46.3 -11,070 -2.27% ✗ $24.8K
Aug 8, 2024 Aug 12, 2024 MCDONALD JOHN T CEO Buy 87.5 +100,000 4.74% ✗ $196.9K
Jun 16, 2024 Jun 17, 2024 Smith Matthew Harnden General Counsel and Secretary Sell 47.5 -1,460 -1.48% ✗ $3.8K
Jun 16, 2024 Jun 17, 2024 Cummings Karen COO Sell 46.3 -7,815 -2.00% ✗ $20.6K
Jun 16, 2024 Jun 17, 2024 Doman Dan Chief Product Officer Sell 46.3 -13,447 -4.12% ✗ $35.4K
Jun 16, 2024 Jun 17, 2024 MCDONALD JOHN T CEO Sell 48.8 -17,834 -0.84% ✗ $46.9K
Jun 16, 2024 Jun 17, 2024 Hill Michael Douglass CFO Sell 46.3 -11,070 -2.22% ✗ $29.1K
Jun 5, 2024 Jun 6, 2024 MCDONALD JOHN T CEO Neutral 52.5 - 0.00% ✗ -
Mar 16, 2024 Mar 19, 2024 MCDONALD JOHN T CEO Sell 45.0 -19,330 -0.90% ✗ $81.4K
Mar 16, 2024 Mar 19, 2024 Hill Michael Douglass CFO Sell 42.5 -12,559 -2.46% ✗ $52.9K
Mar 16, 2024 Mar 19, 2024 Smith Matthew Harnden General Counsel and Secretary Sell 47.5 -1,464 -1.46% ✗ $6.2K
Mar 16, 2024 Mar 19, 2024 Yates Oliver Robert MacFarlane Chief Sales Officer Sell 46.3 -6,672 -2.58% ✗ $28.1K
Mar 16, 2024 Mar 19, 2024 Cummings Karen COO Sell 46.3 -9,515 -2.38% ✗ $40.1K
Mar 16, 2024 Mar 19, 2024 Doman Dan Chief Product Officer Sell 42.5 -15,258 -4.47% ✗ $64.2K
Jan 29, 2024 Mar 11, 2024 MCDONALD JOHN T CEO Neutral 90.0 +250,000 13.19% ✗ -
Feb 6, 2024 Feb 7, 2024 Breslin Matthew Chief Revenue Officer Neutral 90.0 +150,000 100.00% ✗ -
Feb 7, 2024 Breslin Matthew Chief Revenue Officer Neutral 52.5 - 0.00% ✗ -
Jan 29, 2024 Jan 31, 2024 MCDONALD JOHN T CEO Neutral 90.0 +250,000 13.19% ✗ -
Jan 29, 2024 Jan 31, 2024 Doman Dan Chief Product Officer Neutral 90.0 +150,000 78.42% ✗ -
Jan 29, 2024 Jan 31, 2024 Cummings Karen Executive VP & Senior GM Neutral 90.0 +150,000 59.88% ✗ -
Jan 29, 2024 Jan 31, 2024 Yates Oliver Robert MacFarlane Chief Sales Officer Neutral 90.0 +135,000 109.54% ✗ -
Jan 29, 2024 Jan 31, 2024 Hill Michael Douglass CFO Neutral 90.0 +100,000 24.34% ✗ -
Jan 29, 2024 Jan 31, 2024 Smith Matthew Harnden General Counsel and Secretary Neutral 90.0 +50,000 100.00% ✗ -
Jan 6, 2024 Jan 8, 2024 Mattox Timothy Director Neutral 85.0 +27,687 7.21% ✗ -
Jan 8, 2024 Mattox Timothy Director Neutral 52.5 - 0.00% ✗ -
Dec 16, 2023 Dec 19, 2023 Miller Paul Kenneth COO Sell 46.3 -6,561 -3.04% ✗ $30.2K
Dec 16, 2023 Dec 19, 2023 MCDONALD JOHN T CEO Sell 45.0 -11,650 -0.61% ✗ $53.7K
Dec 16, 2023 Dec 19, 2023 Doman Dan Chief Product Officer Sell 46.3 -8,528 -4.27% ✗ $39.3K
Dec 16, 2023 Dec 19, 2023 Cummings Karen Executive VP & Senior GM Sell 46.3 -5,279 -2.06% ✗ $24.3K
Dec 16, 2023 Dec 19, 2023 Yates Oliver Robert MacFarlane Chief Sales Officer Sell 46.3 -2,740 -2.17% ✗ $12.6K
Dec 16, 2023 Dec 19, 2023 Hill Michael Douglass CFO Sell 46.3 -10,004 -2.38% ✗ $46.1K
Nov 21, 2023 Nov 22, 2023 COURTER STEPHEN E Director Sell 22.5 -20,448 -21.60% ✗ $90.6K
Nov 7, 2023 Nov 9, 2023 Doman Dan Chief Product Officer Sell 22.5 -13,996 -6.55% ✗ $67.2K
Oct 31, 2023 Nov 1, 2023 Smith Matthew Harnden General Counsel and Secretary Neutral 90.0 +50,000 100.00% ✗ -
Nov 1, 2023 Smith Matthew Harnden General Counsel and Secretary Neutral 52.5 - 0.00% ✗ -
Sep 16, 2023 Sep 19, 2023 MCDONALD JOHN T CEO Sell 48.8 -11,650 -0.61% ✗ $45K
Sep 16, 2023 Sep 19, 2023 Miller Paul Kenneth COO Sell 46.3 -6,561 -2.95% ✗ $25.3K
Sep 16, 2023 Sep 19, 2023 Doman Dan Chief Product Officer Sell 46.3 -8,528 -3.84% ✗ $32.9K
Sep 16, 2023 Sep 19, 2023 Cummings Karen Executive VP & Senior GM Sell 46.3 -8,323 -3.15% ✗ $32.1K
Sep 16, 2023 Sep 19, 2023 Gill Kinloch III CLO and Secretary Sell 46.3 -6,724 -3.34% ✗ $26K
Sep 16, 2023 Sep 19, 2023 Hill Michael Douglass CFO Sell 46.3 -10,004 -2.32% ✗ $38.6K
Sep 16, 2023 Sep 19, 2023 Yates Oliver Robert MacFarlane Chief Sales Officer Sell 46.3 -2,740 -2.13% ✗ $10.6K
Jul 31, 2023 Aug 2, 2023 Chung David H S Director Neutral 90.0 +62,816 538.36% ✗ -
Jul 31, 2023 Aug 2, 2023 Walsh Teresa Miles Director Neutral 90.0 +62,816 198.32% ✗ -
Jul 31, 2023 Aug 2, 2023 Ross Joe Director Neutral 90.0 +62,816 112.72% ✗ -
Jul 31, 2023 Aug 2, 2023 COURTER STEPHEN E Director Neutral 90.0 +62,816 197.14% ✗ -
Jul 31, 2023 Aug 2, 2023 MAY DAVID Director Neutral 90.0 +62,816 79.90% ✗ -
Jul 7, 2023 Yates Oliver Robert MacFarlane Chief Sales Officer Neutral 52.5 - 0.00% ✗ -
Jul 7, 2023 Cummings Karen Executive VP & Senior GM Neutral 52.5 - 0.00% ✗ -
Jun 16, 2023 Jun 20, 2023 Hill Michael Douglass CFO Sell 46.3 -10,004 -2.27% ✗ $35.3K
Jun 16, 2023 Jun 20, 2023 Doman Dan Chief Product Officer Sell 46.3 -8,528 -3.69% ✗ $30.1K