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Have Flywire Insiders Been Selling Stock?

Simply Wall St·09/05/2026 12:04:00
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We wouldn't blame Flywire Corporation (NASDAQ:FLYW) shareholders if they were a little worried about the fact that Michael Massaro, the CEO & Director recently netted about US$2.1m selling shares at an average price of US$18.39. However, it's crucial to note that they remain very much invested in the stock and that sale only reduced their holding by 6.9%.

The Last 12 Months Of Insider Transactions At Flywire

Notably, that recent sale by Michael Massaro is the biggest insider sale of Flywire shares that we've seen in the last year. That means that an insider was selling shares at below the current price (US$18.55). When an insider sells below the current price, it suggests that they considered that lower price to be fair. That makes us wonder what they think of the (higher) recent valuation. However, while insider selling is sometimes discouraging, it's only a weak signal. This single sale was just 6.9% of Michael Massaro's stake.

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

Check out our latest analysis for Flywire

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NasdaqGS:FLYW Insider Trading Volume September 5th 2026

If you like to buy stocks that insiders are buying, rather than selling, then you might just love this free list of companies. (Hint: Most of them are flying under the radar).

Insider Ownership Of Flywire

Many investors like to check how much of a company is owned by insiders. I reckon it's a good sign if insiders own a significant number of shares in the company. Insiders own 3.4% of Flywire shares, worth about US$77m. While this is a strong but not outstanding level of insider ownership, it's enough to indicate some alignment between management and smaller shareholders.

So What Does This Data Suggest About Flywire Insiders?

Insiders sold stock recently, but they haven't been buying. And even if we look at the last year, we didn't see any purchases. But since Flywire is profitable and growing, we're not too worried by this. Insiders own shares, but we're still pretty cautious, given the history of sales. We'd practice some caution before buying! So these insider transactions can help us build a thesis about the stock, but it's also worthwhile knowing the risks facing this company. Case in point: We've spotted 1 warning sign for Flywire you should be aware of.

Of course Flywire may not be the best stock to buy. So you may wish to see this free collection of high quality 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.