FLYW Flywire Corp Insider Trading

General Counsel Peter Butterfield sold 31,096 shares of FLYW at $18.06 via scheduled 10b5-1 plan; retains 621,056 shares.

Peter Butterfield, General Counsel and Chief Compliance Officer, sold 31,096 shares at $18.06 on 2026-07-01 as part of a pre-arranged 10b5-1 trading plan, reducing his holdings by approximately 4.8%. The sale occurred as the stock has appreciated 27.3% over 30 days and 56.8% over 90 days, trading at $18.33 currently, which is 3.1% below the 52-week high of $18.92. Because this transaction is scheduled under a 10b5-1 plan rather than discretionary, it reflects a predetermined execution schedule rather than a real-time market decision. Butterfield retained substantial holdings of 621,056 shares post-transaction, indicating continued material ownership alignment despite the scheduled sale.

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.

Rob Orgel (then-COO, Flywire) sells 178,980 shares at $17.00 under 10b5-1 plan; stock now $14.61

Rob Orgel, who was COO at the time of the filing, executed a scheduled sale of 178,980 shares at $17.00 via a pre-arranged 10b5-1 trading plan, reducing his holdings by -16.0% to 937,082 shares. The stock is currently trading at $14.61, down -19.1% from its 52-week high of $18.05. Because this transaction is part of a pre-arranged 10b5-1 trading plan, it reflects a scheduled commitment rather than a discretionary trading decision. Across his prior trades at this ticker, measurable outcomes are limited; his only completed prior sale at FLYW (2024-03-05) showed a 90-day return of -37.1%, though the scope and context of that trade differ from this scheduled disposition.

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.

CFO Pitigoi Cosmin sells 35,000 FLYW shares at $17.38; stock at 52-week high after strong rally.

Flywire's CFO Pitigoi Cosmin sold 35,000 shares worth approximately $608,000, reducing his holdings by nearly four percent at a time when the stock is trading at its 52-week high following a significant rally. The company remains profitable with growing revenue, but carries a stretched valuation relative to earnings. This sale marks Cosmin's second open-market disposition—his prior Form 4 activity included one earlier sale and multiple stock-compensation transactions, suggesting a pattern of occasional opportunistic selling rather than consistent open-market activity. The sale occurs during a period of strong price momentum, though without visibility into subsequent stock performance or Cosmin's prior purchase prices, the timing cannot be conclusively characterized as well-timed or poorly-timed. For retail investors, the combination of a C-suite seller exiting at cyclical highs alongside elevated valuation multiples warrants attention, though this single transaction alone does not constitute a full capitulation by insiders.

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.

Voss Capital (10% owner) bought 25,000 FLYW shares at $10.99 on 2026-02-13; stock down 44.4% from 52-week high.

Voss Capital purchased 25,000 shares at $10.99, increasing its stake from 2,275,000 to 2,300,000 shares. The stock is currently at $11.11, down 44.4% from its 52-week high of $19.99 and down 19.4% over the past 30 days. Across his cross-ticker track record of 20 prior open-market buys, Voss Capital's average 90-day return has been -8.6% with a 0.00% win rate, indicating a pattern of purchasing before continued weakness. At Flywire specifically, Voss has made 2 prior purchases (on 2025-12-31 and 2025-12-30), both showing negative 30-day returns of -11.5% and -8.8% respectively. The company has strong fundamentals—$200.1M quarterly revenue with +22.1% annual growth and $29.6M net income—but trades at an extreme P/E of 555.50, suggesting the market has priced in significant future growth or the stock is still recovering from previous overvaluation.

Voss Capital, LP (10% owner) acquired 226,112 shares in 2 purchases for $3,203,277.54 at blended avg $14.17; stock now $14.50 (+7.5% in 30 days)

Voss Capital, LP, a substantial 10% shareholder in Flywire Corp, executed 2 separate open-market purchases totaling 226,112 shares for $3,203,277.54 at a blended average price of $14.17 on 2025-12-30 and 2025-12-31. This accumulation increased holdings from 9,443,888 to 9,670,000 shares (+2.4%). The timing is noteworthy: the stock trades at $14.50 today, 31.8% below its 52-week high of $21.27, yet the 30-day return has been +7.5%, suggesting a recent recovery. Voss Capital's cross-ticker insider history shows a 100% win rate over 90-day periods across 13 prior buys (average 90-day return +7.8%), though this track record spans multiple tickers, not Flywire-specific trading. The company itself shows solid growth (revenue +22.1% YoY, $200.1M latest quarter, $29.6M net income) but carries an elevated P/E of 725.00 relative to earnings quality, leaving valuation questions unresolved by this filing alone.

Director Howard Gretchen buys 8,889 shares of FLYW at $10.94; holdings rise 40.6% to 30.8K shares amid 62.7% decline from 52-week high.

Director Howard Gretchen purchased 8,889 shares at $10.94 on 2025-02-27, expanding his holdings by 40.6% from 21,881 to 30,770 shares. The purchase occurs as the stock trades 62.7% below its 52-week high of $28.85, following a 52.6% decline over the past 90 days. While Flywire demonstrates solid operational metrics—annual revenue growth of +22.1%, net income of $38.9M on revenue of $156.8M, and a market cap of $1.3B—the elevated P/E of 41.38 and the sharp recent price deterioration create ambiguity about whether this acquisition reflects conviction or a tactical entry into a depressed valuation. The director's significant increase in ownership stake merits investor attention given the pronounced price weakness.