Stock Analysis

Insiders Sold Upland Software At US$2.45, Meanwhile Stock Sits Near US$1.91

Upland Software, Inc.'s (NASDAQ:UPLD) stock price has dropped 10% in the previous week, but insiders who sold US$84k in stock over the past year have had less luck. Insiders might have been better off holding onto their shares, given that the average selling price of US$2.45 is still below the current share price.

While insider transactions are not the most important thing when it comes to long-term investing, logic dictates you should pay some attention to whether insiders are buying or selling shares.

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The Last 12 Months Of Insider Transactions At Upland Software

The Director, Timothy Mattox, made the biggest insider sale in the last 12 months. That single transaction was for US$50k worth of shares at a price of US$2.64 each. While insider selling is a negative, to us, it is more negative if the shares are sold at a lower price. The silver lining is that this sell-down took place above the latest price (US$1.91). So it may not tell us anything about how insiders feel about the current share price.

Upland Software insiders didn't buy any shares over the last year. You can see the insider transactions (by companies and individuals) over the last year depicted in the chart below. By clicking on the graph below, you can see the precise details of each insider transaction!

See our latest analysis for Upland Software

insider-trading-volume
NasdaqGM:UPLD Insider Trading Volume November 5th 2025

If you are like me, then you will not want to miss this free list of small cap stocks that are not only being bought by insiders but also have attractive valuations.

Insiders At Upland Software Have Sold Stock Recently

We have seen a bit of insider selling at Upland Software, over the last three months. Founder John McDonald sold just US$34k worth of shares in that time. It's not great to see insider selling, nor the lack of recent buyers. But the selling simply isn't sufficiently substantial to be of much use as a signal.

Insider Ownership

Many investors like to check how much of a company is owned by insiders. A high insider ownership often makes company leadership more mindful of shareholder interests. Upland Software insiders own about US$14m worth of shares. That equates to 23% of the company. While this is a strong but not outstanding level of insider ownership, it's enough to indicate some alignment between management and smaller shareholders.

What Might The Insider Transactions At Upland Software Tell Us?

Our data shows a little more insider selling, but no insider buying, in the last three months. But the sales were small, so we're not concerned. Recent sales exacerbate our caution arising from analysis of Upland Software insider transactions. But we do like the fact that insiders own a fair chunk of the company. So while it's helpful to know what insiders are doing in terms of buying or selling, it's also helpful to know the risks that a particular company is facing. For example - Upland Software has 3 warning signs we think you should be aware of.

But note: Upland Software may not be the best stock to buy. So take a peek at this free list of interesting companies with high ROE and low debt.

For the purposes of this article, insiders are those individuals who report their transactions to the relevant regulatory body. We currently account for open market transactions and private dispositions of direct interests only, but not derivative transactions or indirect interests.

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This article by Simply Wall St is general in nature. We provide commentary based on historical data and analyst forecasts only using an unbiased methodology and our articles are not intended to be financial advice. It does not constitute a recommendation to buy or sell any stock, and does not take account of your objectives, or your financial situation. We aim to bring you long-term focused analysis driven by fundamental data. Note that our analysis may not factor in the latest price-sensitive company announcements or qualitative material. Simply Wall St has no position in any stocks mentioned.