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 Massaro sells 150,000 FLYW shares at $12.31; prior 5 sales at FLYW all well-timed with negative 90d returns averaging -37.8%

Michael Massaro, CEO, sold 150,000 shares (150.0K shares) of Flywire Corp (FLYW) at $12.31 on 2026-03-02 for $1,846,140.00, reducing his holdings to 2,801,948 shares (2.80M shares), a -5.1% reduction in his stake. This transaction is significant in context of his timing pattern: his prior 5 sales at FLYW—on 2024-03-20 (×2), 2024-03-19 (×2), and 2024-03-05—were all well-timed at the 90-day mark, with negative 90-day returns averaging -37.8%, indicating the stock fell after each sale. His cross-ticker track record shows an even more robust pattern: 20 prior sells with a 100.00% well-timed rate and an average 90-day return of -30.5%. The current sale at $12.31 sits -13.2% below the 52-week high of $14.81, and the stock has declined -6.7% over the past 90 days, positioning this transaction within a pattern of selling into relative strength or near highs. The company's valuation is notably elevated at a P/E of 183.57 despite solid fundamentals (revenue $200,138,000.00 with +26.6% annual growth and net income $29,631,000.00), which underscores the relevance of an insider reduction at this juncture.