Flywire Corp (FLYW) reported that Peter Butterfield, its General Counsel and Chief Compliance Officer, had 7,878 shares of Voting Common Stock withheld on September 1, 2026 to satisfy income tax withholding and remittance obligations related to net settlement of time-based RSU awards. This was not an open market sale, and he continued to hold 613,178 shares directly after the transaction.
Flywire Corp (FLYW) insider David R. King, Chief Product Officer & Co‑President of Global Education, reported a tax-withholding disposition of 15,971 shares of Voting Common Stock on September 1, 2026. The shares were withheld by Flywire to satisfy income tax withholding obligations related to the net settlement of time-based restricted stock unit awards and do not represent an open market sale.
After this transaction, King held 1,075,679 shares of Voting Common Stock directly. An additional 276,204 shares are held indirectly by the D R King Revocable Trust Dated 10/05/07, where King is a trustee and disclaims beneficial ownership except to the extent of any pecuniary interest.
Flywire Corp (FLYW) reported that Chief Financial Officer Cosmin Pitigoi had 21,673 shares of Voting Common Stock withheld on September 1, 2026 to satisfy income tax withholding and remittance obligations arising from the net settlement of time-based restricted stock unit awards. The company states this was not an open market sale. Following this tax-withholding disposition, Pitigoi beneficially holds 856,575 shares of Flywire common stock directly. No Rule 10b5-1 trading plan is reported for this transaction.
Flywire Corp (FLYW) reported that Chief Payments Officer Mohit Kansal disposed of Voting Common Stock in two transactions. On September 1, 2026, 9,923 shares were withheld to satisfy income tax obligations related to net settlement of time-based RSU awards, which did not involve any open-market sale. On September 2, 2026, he sold 12,423 shares in open-market or private transactions at a weighted average price of $18.6945 per share, executed under a previously adopted Rule 10b5-1 trading plan, with individual sale prices ranging from $18.04 to $19.04.
Flywire Corp (FLYW) reported that Chief Executive Officer and director Michael Massaro disposed of Voting Common Stock on September 1, 2026. 39,993 shares were withheld at $18.185 per share to cover income tax obligations on net-settled restricted stock units, which was not an open-market sale, and 112,500 shares were sold at a weighted-average price of $18.3883 per share under a previously adopted Rule 10b5-1 trading plan. The filing also notes indirect holdings in family trusts for which Massaro disclaims beneficial ownership except for any pecuniary interest.
Flywire Corp (FLYW) received a notice under Rule 144 that stockholder Mohit Kansal intends to sell up to 12,464 shares of common stock through Fidelity Brokerage Services LLC. The shares were acquired on September 1, 2026 via restricted stock vesting as compensation. In the past three months, Kansal sold 54,543 shares on June 15, 2026 and 3,650 shares on June 25, 2026. Flywire had 121,667,674 shares outstanding as of September 2, 2026, listed on NASDAQ.
Flywire Corp (FLYW) had insider activity reported by a group of ten percent owners associated with Voss Capital. On 2026-08-28, accounts managed by Voss Capital sold a total of 44,768 shares of voting common stock in open market or private transactions at $18.7823 per share, held indirectly in Voss Managed Accounts. The filing also reports indirect holdings of 2,250,000 shares by Voss Value Master Fund, LP and 366,617 shares by Voss Value-Oriented Special Situations Fund, LP, along with call options over 150,000 underlying shares with exercise prices of $10.00 and $7.50 per share.
Flywire Corp (FLYW) had significant insider-related activity reported by a group of Voss-managed entities that collectively beneficially own over 10% of the common stock. On August 26–27, 2026, entities associated with Voss Capital, LP sold a total of 120,021 shares of voting common stock in open-market or private transactions at weighted average prices around $18.9 per share, with actual trade prices ranging from approximately $18.78 to $19.08. The sales were made indirectly through Voss Value-Oriented Special Situations Fund, LP and certain managed accounts of Voss Capital, LP.
As of August 26, 2026, Voss Value Master Fund, LP continued to hold 2,250,000 shares of Flywire voting common stock indirectly. In addition, managed accounts of Voss Capital, LP held call options immediately exercisable into 100,000 underlying shares at a $10.00 strike expiring September 18, 2026, and 50,000 underlying shares at a $7.50 strike expiring December 18, 2026. Each reporting person disclaims beneficial ownership beyond its pecuniary interest.
Flywire Corp (FLYW) reported insider activity by a group of greater-than-10% holders associated with Voss Capital and Travis W. Cocke. On August 24–25, 2026, entities they manage sold a total of 274,273 shares of voting common stock in open-market transactions at weighted-average prices around $19.19–$19.49 per share, through Voss Value-Oriented Special Situations Fund and certain Voss-managed accounts. The group also reports indirect ownership of 2,250,000 shares held by Voss Value Master Fund and holds immediately exercisable call options over an additional 150,000 underlying shares at exercise prices of $10.00 and $7.50. The reporting persons collectively disclaim beneficial ownership beyond their pecuniary interests.
Flywire Corp (FLYW) received a Form 4 reporting that investment entities associated with Voss Capital, LP, which are part of a group owning over 10% of Flywire’s common stock, executed open-market sales of the company’s voting common stock. On August 18–19, 2026, these entities sold a total of 104,500 shares at prices ranging from $18.2368 to $18.8595 per share through Voss Value Master Fund, LP and certain managed accounts of Voss Capital. The filing also reports an indirect holding of 375,000 shares by Voss Value-Oriented Special Situations Fund, LP, plus call options, held in managed accounts, that are immediately exercisable to acquire up to 100,000 shares at $10.00 per share expiring September 18, 2026 and 50,000 shares at $7.50 per share expiring December 18, 2026. The reporting persons disclaim beneficial ownership of these securities except to the extent of their pecuniary interest.