Upland Software, Inc. (UPLD) is a publicly traded company in the Unknown sector. Across all available filings, 26 corporate insiders have executed 596 transactions totaling $189.6M, demonstrating a bearish sentiment with -$136.5M in net insider flow. The most recent transaction on Feb 23, 2026 involved a transaction of 150,000 shares valued at $0.
No significant insider buying has been recorded for UPLD in the recent period.
No significant insider selling has been recorded for UPLD in the recent period.
Based on recent SEC filings, insider sentiment for UPLD is bearish with an Insider Alignment Score of 14/100 and a net flow of -$136.5M. Insiders are reducing their positions, though this can be driven by factors unrelated to company outlook.
Insider trading at Upland Software, Inc. (UPLD) refers to stock transactions made by corporate insiders—executives, directors, and beneficial owners holding more than 10% of the company's shares. These individuals have access to material non-public information and are required by law to report their trades to the SEC within two business days. Currently, 26 insiders are actively trading UPLD stock, having executed 596 transactions in the past 90 days. The most active insider is Joseph Liemandt (Executive), who has made 65 transactions totaling $96.5M.
Get notified when executives and directors at UPLD file new Form 4 transactions
Date | Insider | Title | Type | Shares | Price | Value | Flags |
|---|---|---|---|---|---|---|---|
| Feb 23, 2026 | Doman Dan | Chief Operating & Product Ofcr | Award | 150,000 | $N/A | $0 | C-Suite |
| Feb 23, 2026 | Douglass Hill Michael | CFO, Treasurer & Secretary | Award | 70,000 | $N/A | $0 | C-Suite |
| Dec 16, 2025 | Douglass Hill Michael | Executive | Payment | 8,856 | $1.49 | $13.2K | |
| Dec 16, 2025 | T. Mcdonald John | Executive | Payment | 19,677 | $1.49 | $29.3K | |
| Dec 16, 2025 | Doman Dan | Executive | Payment | 24,595 | $1.49 | $36.6K | |
| Oct 27, 2025 | Miles Walsh Teresa | Executive | Award | 25,000 | $N/A | $0 | |
| Oct 27, 2025 | May David | Executive | Award | 25,000 | $N/A | $0 | |
| Oct 27, 2025 | Mattox Timothy | Executive | Award | 25,000 | $N/A | $0 | |
| Oct 27, 2025 | E. Courter Stephen | Executive | Award | 25,000 | $N/A | $0 | |
| Oct 27, 2025 | H. S. Chung David | Executive | Award | 25,000 | $N/A | $0 | |
| Sep 16, 2025 | Doman Dan | Executive | Payment | 26,236 | $2.48 | $65.1K | |
| Sep 16, 2025 | Douglass Hill Michael | Executive | Payment | 11,152 | $2.48 | $27.7K | |
| Sep 16, 2025 | T. Mcdonald John | Executive | Payment | 22,956 | $2.48 | $56.9K | |
| Sep 11, 2025 | T. Mcdonald John | Executive | Sale | 14,438 | $2.36 | $34.1K | |
| Jun 30, 2025 | Cummings Karen | Executive | Payment | 40,993 | $1.95 | $79.9K |
| TYPE | COUNT | VALUE | % |
|---|---|---|---|
Sale(S) | 170 | $163.0M | 70.9% |
Purchase(P) | 146 | $26.5M | 11.5% |
Payment(F) | 131 | $22.3M | 9.7% |
Award(A) | 84 | $17.1M | 7.5% |
Exercise(M) | 12 | $885.6K | 0.4% |
Gift(G) | 14 | $0 | 0.0% |
Other(J) | 8 | $0 | 0.0% |
Conversion(C) | 31 | $0 | 0.0% |
Insider selling pressure at Upland Software, Inc. has increased, with 26 insiders executing 596 transactions across all time. Total sales of $163.0M significantly outpace purchases of $26.5M, resulting in a net outflow of $136.5M. This selling activity appears largely discretionary, which may warrant closer attention from investors.