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Don't Ignore The Insider Selling In Twilio
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We wouldn't blame Twilio Inc. (NYSE:TWLO) shareholders if they were a little worried about the fact that Khozema Shipchandler, the CEO & Director recently netted about US$4.1m selling shares at an average price of US$294. However, it's crucial to note that they remain very much invested in the stock and that sale only reduced their holding by 6.7%.

Twilio Insider Transactions Over The Last Year

In fact, the recent sale by Khozema Shipchandler was the biggest sale of Twilio shares made by an insider individual in the last twelve months, according to our records. That means that even when the share price was slightly below the current price of US$301, an insider wanted to cash in some shares. As a general rule we consider it to be discouraging when insiders are selling below the current price, because it suggests they were happy with a lower valuation. Please do note, however, that sellers may have a variety of reasons for selling, so we don't know for sure what they think of the stock price. It is worth noting that this sale was only 6.7% of Khozema Shipchandler's holding.

Insiders in Twilio didn't buy any shares in the last year. You can see a visual depiction of insider transactions (by companies and individuals) over the last 12 months, below. If you click on the chart, you can see all the individual transactions, including the share price, individual, and the date!

See our latest analysis for Twilio

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NYSE:TWLO Insider Trading Volume October 6th 2026

For those who like to find hidden gems this free list of small cap companies with recent insider purchasing, could be just the ticket.

Does Twilio Boast High Insider Ownership?

Looking at the total insider shareholdings in a company can help to inform your view of whether they are well aligned with common shareholders. I reckon it's a good sign if insiders own a significant number of shares in the company. It's great to see that Twilio insiders own 0.3% of the company, worth about US$144m. Most shareholders would be happy to see this sort of insider ownership, since it suggests that management incentives are well aligned with other shareholders.

What Might The Insider Transactions At Twilio Tell Us?

Insiders haven't bought Twilio stock in the last three months, but there was some selling. Looking to the last twelve months, our data doesn't show any insider buying. But since Twilio is profitable and growing, we're not too worried by this. While insiders do own a lot of shares in the company (which is good), our analysis of their transactions doesn't make us feel confident about the company. While it's good to be aware of what's going on with the insider's ownership and transactions, we make sure to also consider what risks are facing a stock before making any investment decision. When we did our research, we found 3 warning signs for Twilio (1 is concerning!) that we believe deserve your full attention.

Of course, you might find a fantastic investment by looking elsewhere. So take a peek at this free list of interesting companies.

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.

Disclaimer:This article represents the opinion of the author only. It does not represent the opinion of Webull, nor should it be viewed as an indication that Webull either agrees with or confirms the truthfulness or accuracy of the information. It should not be considered as investment advice from Webull or anyone else, nor should it be used as the basis of any investment decision.
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