Michael Massaro

CEO Massaro sells 50,000 FLYW shares at $15.26; scheduled 10b5-1 plan; retains 2.68M shares.

CEO Michael Massaro sold 50,000 shares (50.0K shares) of Flywire Corp at $15.26 on 2026-06-15 through a pre-arranged 10b5-1 trading plan, reducing his holdings by 1.8% from 2.73M shares to 2.68M shares. The transaction is scheduled rather than discretionary, eliminating timing-based inference. Massaro's prior trades at FLYW show mixed returns: two 2026-05-06 sells recorded -13.4% and -8.0% at 30 days; his 2026-03-02 FLYW sale was -5.9% at 30 days but +30.3% at 90 days; and two 2024-03-20 FLYW sales each delivered -15.8% at 30 days and -38.6% at 90 days. Stock performance since this sale has been negative: current price of $15.42 is -14.6% from the 52-week high and -3.8% in the past 30 days, though it is +29.7% over 90 days. The company shows solid fundamentals with annual revenue growth of +26.6%, latest quarterly revenue of $188.1M, and net income of $12.5M, though the P/E of 61.68 reflects elevated valuation expectations.

CEO Michael Massaro sold 50,000 shares for $819,686; stock rallying sharply and trading at 52-week highs.

Michael Massaro, Flywire's CEO, disposed of 50,000 shares as the stock trades at its 52-week highs following a sharp rally over recent months. This contrasts with his track record at this ticker: his most recent prior sale saw the stock decline in the following month before recovering substantially—a conflicting timing signal. His Form 4 history shows he has been almost exclusively a seller, with no open-market purchases in the prior three-year window, suggesting this remains a liquidation rather than a rebalancing move. The company itself is profitable with strong revenue growth, so the sale appears motivated by valuation or portfolio management rather than deteriorating fundamentals. The fact that Massaro is selling near all-time highs while the company continues to expand profitably adds context, though his prior sales at this ticker have ultimately underperformed as the stock rose afterward over longer periods.

CEO Michael Massaro sold 150,000 shares of FLYW at $12.31 under pre-arranged 10b5-1 plan

Michael Massaro, Chief Executive Officer of Flywire Corp, sold 150,000 shares (150.0K shares) on 2026-03-02 at $12.31 per share for a total value of $1,846,140.00 ($1.8M), reducing his holdings from 2,951,948 shares to 2,801,948 shares. This transaction was executed under a pre-arranged 10b5-1 trading plan, meaning it was scheduled and non-discretionary rather than a response to current market conditions. The sale represents a 5.1% reduction in his pre-transaction holdings. As a Rule 10b5-1 plan transaction, this reflects a predetermined execution schedule rather than a timing decision, and investors should assess this activity in that context.