NASDAQ:UPLD

Upland Software Stock Insider Trading

Technology > Software - Application

Buy UPLD

*Your capital is at risk

$4.90

+0.155 (+3.27%)

At Close: Jul 02, 2026

Upland Software Stock Insider Power

Based on the 100 latest insides trades, we have calculated the insider power to be positive at 93.33. In total, the insiders bought 5.82M and sold 1.52M UPLD shares in the last 100 trades. The insider score can be negative despite buy/sell ratio being positive. The score focuses on the quality of the trades.

Insider Power (Last 100 transactions)	93.33
● Buy	5.82M shares
● Sell	1.52M shares
39% Buy Activity Negligible or No Correlation
Sell Signal Low Confidence Apr 30, 2026 Analysis Breakdown: Signal is highly questionable due to a strongly contradictory positive Insider Power Score of 93.33. Confidence increased due to high data reliability score of 100.

Historical Insider Trades

Date	Type	Person	Role	Amount
Jun 16, 2026 Sell	Common Stock F-InKind	Hill Michael Douglass CFO, Treasurer & Secretary	C-Suite Officer	8 931 Value: $5K
Jun 16, 2026 Sell	Common Stock F-InKind	Nathaniel Sean CEO And President	CEO / President	18 605 Value: $11.3K
Jun 16, 2026 Sell	Common Stock F-InKind	Doman Dan Chief Operating & Product Ofcr	Officer	29 515 Value: $17.9K
Jun 04, 2026 Buy	Common Stock A-Award	Nathaniel Sean CEO And President	CEO / President	500 000 Value: $3.85M
Jun 04, 2026 Buy	Performance-based Restricted Stock Unit June 2026 A-Award	Nathaniel Sean CEO And President	CEO / President	133 333 Value: $1.03M
May 01, 2026 Buy	Common Stock	Nathaniel Sean CEO And President	CEO / President	0 Value: $0
Apr 30, 2026 Buy	Common Stock A-Award	Mcdonald John T Director	Director	250 000 Value: $1.56M
Apr 30, 2026 Sell	Performance Share Unit D-Return	Mcdonald John T Director	Director	250 000 Value: $0
Mar 16, 2026 Sell	Common Stock F-InKind	Doman Dan Chief Operating & Product Ofcr	Officer	33 491 Value: $18.1K
Mar 16, 2026 Sell	Common Stock F-InKind	Hill Michael Douglass CFO, Treasurer & Secretary	C-Suite Officer	8 931 Value: $5K
Mar 16, 2026 Sell	Common Stock F-InKind	Mcdonald John T CEO	CEO / President	18 605 Value: $10.0K
Feb 27, 2026 Buy	Common Stock A-Award	Doman Dan Chief Operating & Product Ofcr	Officer	100 000 Value: $883.0K
Feb 23, 2026 Buy	Common Stock A-Award	Doman Dan Chief Operating & Product Ofcr	Officer	150 000 Value: $1.41M
Feb 23, 2026 Buy	Common Stock A-Award	Hill Michael Douglass CFO, Treasurer & Secretary	C-Suite Officer	70 000 Value: $659.5K
Dec 16, 2025 Sell	Common Stock F-InKind	Hill Michael Douglass CFO, Treasurer & Secretary	C-Suite Officer	8 856 Value: $13.2K
Dec 16, 2025 Sell	Common Stock F-InKind	Doman Dan Chief Operating & Product Ofcr	Officer	24 595 Value: $36.5K
Dec 16, 2025 Sell	Common Stock F-InKind	Mcdonald John T CEO	CEO / President	19 677 Value: $29.2K
Oct 27, 2025 Buy	Common Stock A-Award	Walsh Teresa Miles Director	Director	25 000 Value: $530.0K
Oct 27, 2025 Buy	Common Stock A-Award	May David Director	Director	25 000 Value: $530.0K
Oct 27, 2025 Buy	Common Stock A-Award	Mattox Timothy Director	Director	25 000 Value: $530.0K
Oct 27, 2025 Buy	Common Stock A-Award	Courter Stephen E Director	Director	25 000 Value: $530.0K
Oct 27, 2025 Buy	Common Stock A-Award	Chung David H S Director	Director	25 000 Value: $530.0K
Sep 16, 2025 Sell	Common Stock F-InKind	Mcdonald John T CEO	CEO / President	22 956 Value: $56.9K
Sep 16, 2025 Sell	Common Stock F-InKind	Hill Michael Douglass CFO, Treasurer & Secretary	C-Suite Officer	11 152 Value: $27.7K
Sep 16, 2025 Sell	Common Stock F-InKind	Doman Dan Chief Operating & Product Ofcr	Officer	26 236 Value: $65.1K

About Insider Power

Insider Power is a proprietary algorithm developed by StockInvest.us to evaluate the significance of insider transactions. The calculation considers the size, type, and timing of transactions, as well as the insider’s role within the company.

It is important to note that, in general, there is little to no correlation between insider transactions and short-term stock price movements. In one of our studies, only 0.22%^* of stocks with insider activity showed a measurable correlation — and even then, it was unclear whether the effect was caused by insider actions or simply by the stock’s broader trend.

While our algorithms are designed to highlight potentially meaningful signals, these cannot be regarded as statistically significant on their own. Insider trading activity should therefore be seen as informative rather than as direct trading guidance. The Insider Power metric was created to present this information in a clearer and more accessible way, helping investors better understand the possible context of insider activity.

* October 6th, 2025 - Tested on 5562 stocks

ABOUT UPLAND SOFTWARE

Upland Software, Inc. provides cloud-based enterprise work management software in the United States, the United Kingdom, Canada, and internationally. It offers a family of software applications under the Upland brand in the areas of marketing, sales, contact center, project management, information technology, business operations, and human resources and legal. The company also provides professional services, such as implementation, data extractio...

Read Full Profile Here