Every Form 4 that Flywire Corp (FLYW) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow FLYW and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full FLYW filings page.
Flywire Corp (FLYW) reported that President and COO Rob Orgel had 21,979 shares of Voting Common Stock withheld on September 1, 2026 to satisfy income tax withholding obligations tied to the net settlement of time-based RSU awards; this was not an open market sale. After these withholdings and including 1,815 shares acquired under the Employee Stock Purchase Plan, Orgel directly holds 916,918 shares of Flywire common stock.
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) 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.
Flywire Corp director Phillip John Riese reported an option exercise and share sale. He exercised a stock option for 48,000 shares of Voting Common Stock at an exercise price of $0.59 per share, fully vesting the option. On the same date, he sold 36,000 shares of Voting Common Stock at a weighted average price of $18.2231 per share in multiple transactions priced between $18.200 and $18.285. The exercised option covered 48,000 shares and now shows 0 derivative shares remaining.
Flywire Corp CEO Michael Massaro reported sales of 125,000 shares of Voting Common Stock on July 16–17, 2026, at weighted‑average prices of $18.6219 and $18.1977 per share, executed under a previously adopted Rule 10b5‑1 trading plan. After these sales, he directly holds 2,553,051 shares and has indirect interests in 192,193 and 307,548 shares held in family trusts, for which he disclaims beneficial ownership except for any pecuniary interest.
Flywire Corp General Counsel and CCO Peter Butterfield reported an open-market sale of 31,096 shares of Voting Common Stock on July 1, 2026. The shares were sold at a weighted average price of $18.0558, in multiple trades between $18.00 and $18.12 per share, under a previously adopted Rule 10b5-1 trading plan. Following this transaction, Butterfield directly owns 621,056 shares of Flywire common stock.
Flywire Corp executive David R. King exercised stock options to acquire 5,125 shares of Voting Common Stock at $3.95 per share. These shares were acquired through the exercise of an Employee Stock Option that is fully vested.
After this transaction, he directly holds 1,091,650 shares of Voting Common Stock and has an additional 276,204 shares reported as indirectly owned through the D R King Revocable Trust. The trust holdings are reported with a disclaimer of beneficial ownership, meaning his economic interest is limited to any pecuniary interest he may have in the trust.
Flywire Corp’s Chief Payments Officer Mohit Kansal executed an open-market sale of 3,650 shares of Voting Common Stock at $16.96 per share. The transaction was carried out under a previously adopted Rule 10b5-1 trading plan, indicating it was pre-planned. Following the sale, Kansal directly holds 500,670 shares, so the trade represents only a small portion of his overall position.
Flywire Corp Chief Payments Officer Mohit Kansal sold 54,543 shares of Voting Common Stock in an open-market transaction. The shares were sold at a weighted average price of $15.1549 per share, with individual trade prices ranging from $14.79 to $15.50.
After this sale, Kansal directly holds 504,320 shares of Flywire common stock, which reflects an adjustment for 990 shares acquired under the company’s Employee Stock Purchase Plan. The sale was carried out under a previously adopted Rule 10b5-1 trading plan, indicating it was pre-scheduled rather than timed discretionarily.
Flywire Corp Chief Executive Officer Michael Massaro reported an open-market sale of 50,000 shares of Voting Common Stock on June 15, 2026. The shares were sold at a weighted average price of $15.2588 per share under a previously adopted Rule 10b5-1 trading plan.
After this transaction, Massaro directly holds 2,678,051 shares of Voting Common Stock. Additional shares are held indirectly through the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust, where his spouse serves as trustee and he disclaims beneficial ownership except for any pecuniary interests.
Flywire Corp General Counsel and Chief Compliance Officer Peter Butterfield reported an open-market sale of 6,528 shares of Voting Common Stock on June 15, 2026 at a weighted average price of $15.0766 per share.
The sale was made under a previously adopted Rule 10b5-1 trading plan, indicating it was pre-scheduled rather than timed discretionarily. Following this transaction, Butterfield directly holds 652,152 shares of Flywire common stock.
Flywire Corp director Edwin J. Santos sold shares in an open-market transaction. On 2026-06-08, he sold 6,524 shares of Voting Common Stock at a weighted average price of $14.1206 per share.
After this sale, Santos directly holds 11,558 shares of Flywire Voting Common Stock. According to the footnote, the sale occurred through multiple trades at prices ranging from $14.12 to $14.125 per share.
Flywire Corp General Counsel and Chief Compliance Officer Peter Butterfield reported a single open-market sale of 6,188 shares of Voting Common Stock on June 5, 2026 at a weighted average price of $14.401 per share.
The sale was executed under a previously adopted Rule 10b5-1 trading plan. Following this transaction, Butterfield directly holds 658,680 shares, a figure that is adjusted to reflect 704 shares acquired through Flywire’s Employee Stock Purchase Plan.
Flywire Corp director Edwin J. Santos reported an open-market sale of 10,466 shares of Voting Common Stock on June 4, 2026. The weighted average sale price was $14.687 per share, with individual trades executed between $14.535 and $14.845 per share. Following this transaction, Santos directly holds 18,082 shares of Flywire common stock.
Harris Matthew C reported acquisition or exercise transactions in this Form 4 filing.
Flywire Corp director Matthew C. Harris received a new equity grant in the form of restricted stock units. The award covers 11,558 shares of Voting Common Stock at no cash cost, reflecting stock-based compensation rather than an open-market purchase.
The restricted stock units vest on the earlier of June 2, 2027 or Flywire’s next annual meeting of stockholders, as long as Harris continues serving the company until that date. The units will fully vest sooner if there is a change in control of Flywire or upon Harris’s death or disability. After this grant, he holds 39,014 shares of Voting Common Stock directly.
Flywire Corp director Phillip John Riese reported a mix of equity awards, option exercise, and routine share sales. He received 11,558 voting common shares as a restricted stock unit award that will vest on the earlier of June 2, 2027 or the company’s next annual stockholder meeting, with accelerated vesting upon a change in control, death, or disability.
Riese exercised options to acquire 5,000 voting common shares at $0.59 per share and sold a total of 5,000 shares in open-market transactions at weighted average prices around the mid-$15 to $16 range under a previously adopted Rule 10b5-1 trading plan. After these transactions, he directly holds 234,493 shares of voting common stock and 48,000 fully vested stock options.
Finkelstein Alex reported acquisition or exercise transactions in this Form 4 filing.
Flywire Corp director Alex Finkelstein received an equity grant of 11,558 shares of Voting Common Stock in the form of restricted stock units. These units vest on the earlier of June 2, 2027, or the company’s next annual stockholder meeting, as long as he continues to serve.
The award will also fully vest sooner if there is a change in control of the company, or upon his earlier death or disability. Following this grant, Finkelstein directly holds 270,831 shares of Flywire common stock, reflecting routine director compensation rather than an open-market purchase.
Santos Edwin J reported acquisition or exercise transactions in this Form 4 filing.
Flywire Corp director Edwin J. Santos received an equity award of 11,558 shares of Voting Common Stock as a restricted stock unit grant. The award was made at no cash cost per share and increases his direct holdings to 28,548 shares.
The restricted stock units vest on the earlier of June 2, 2027, or Flywire’s next annual stockholder meeting, as long as he continues providing service through that date. The units will also fully vest earlier if there is a change in control of the company, or upon his death or disability.
Jaques Carleigh reported acquisition or exercise transactions in this Form 4 filing.
Flywire Corp director Carleigh Jaques received a new equity award in the form of restricted stock units. The grant covers 11,558 shares of Voting Common Stock at no purchase price, bringing her direct holdings to 44,152 shares. These units vest on the earlier of June 2, 2027 or the company’s next annual stockholder meeting, assuming continued service, and will fully accelerate upon a change in control, death, or disability.
Offereins Diane E reported acquisition or exercise transactions in this Form 4 filing.
Flywire Corp director Diane E. Offereins reported an equity grant of 11,558 shares of Voting Common Stock in the form of restricted stock units. The award was granted at no cash cost and will vest on the earlier of June 2, 2027, or Flywire’s next annual stockholder meeting, if she remains in continuous service. The units will fully vest sooner if there is a change in control or upon her death or disability. After this grant, she directly holds 58,777 shares.
Flywire Corp director Gretchen Howard received a grant of 11,558 shares of Voting Common Stock as a restricted stock unit award. This is a compensation-related acquisition at no cash cost per share. Following the grant, she holds 59,318 shares directly.
The restricted stock units vest on the earlier of June 2, 2027, or Flywire’s next annual meeting of stockholders, provided she continues to serve the company through that date. The award will also fully vest if there is a change in control of Flywire, or upon her earlier death or disability.
Katziff Christine reported acquisition or exercise transactions in this Form 4 filing.
Flywire Corp director Christine Katziff received an award of 11,558 shares of Voting Common Stock in the form of restricted stock units. These units were granted at no cash cost and will vest on the earlier of June 2, 2027, or Flywire’s next annual stockholder meeting, as long as she continues serving the company. The award will fully vest sooner if there is a change in control of Flywire, or upon her earlier death or disability. After this grant, she holds 39,783 shares directly.
Flywire Corp insider David R. King reported routine share activity related to tax withholding. On June 1, 2026, 15,970 shares of Voting Common Stock were withheld at $16.61 per share to satisfy income tax obligations from the net settlement of time-based restricted stock unit awards. The filing specifies this was not an open market sale. After this tax-withholding disposition, King directly held 1,084,710 shares of Voting Common Stock. Separately, a revocable trust associated with King held 276,204 shares, with beneficial ownership disclaimed except for any pecuniary interest.
Flywire Corp Chief Executive Officer Michael Massaro reported a routine tax-related share disposition. The company withheld 39,799 shares of voting common stock at $16.61 per share to satisfy income tax withholding from the net settlement of time-based restricted stock units, and this was not an open market sale. After this event, he directly holds 2,726,236 shares of voting common stock. Additional shares, including 307,548 held by the M Massaro Trust and 192,193 held by the Michael P. Massaro 2021 Irrevocable Trust, are reported as indirect holdings, with Massaro disclaiming beneficial ownership except for any pecuniary interest.
Flywire Corp Chief Payments Officer Mohit Kansal reported a tax-related share disposition. On June 1, 2026, 9,921 shares of Voting Common Stock were withheld at $16.61 per share to cover income tax obligations tied to vested restricted stock units.
The footnote clarifies this was not an open-market sale but issuer withholding as part of net settlement. After this transaction, Kansal directly owned 557,873 shares of Flywire common stock.
Flywire Corp President and COO Rob Orgel reported share dispositions. On June 1, 2026, he sold 178,980 shares of Voting Common Stock in an open-market transaction at $17.00 per share under a previously adopted Rule 10b5-1 trading plan.
On the same date, 21,979 shares were withheld at $16.61 per share to cover income tax obligations tied to net settlement of restricted stock units, which was not an open-market sale. After these transactions, he directly holds 937,082 shares of Voting Common Stock.
Flywire Corp's Chief Financial Officer, Cosmin Pitigoi, reported a routine tax-related share disposition. On the transaction date, 18,890 shares of Voting Common Stock were withheld by the company at a price of $16.61 per share to cover income tax obligations tied to vested restricted stock units.
The filing specifies this was a net settlement and not an open market sale. After this withholding, Pitigoi directly holds 878,248 shares of Flywire common stock. This type of transaction reflects standard tax withholding mechanics rather than a discretionary decision to sell shares in the market.
Flywire Corp General Counsel and CCO Peter Butterfield reported a tax-related share withholding. On this Form 4, the issuer withheld 7,318 shares of Voting Common Stock at $16.61 per share to cover income tax obligations tied to restricted stock unit vesting, which the footnote states does not represent an open-market sale.
After this non-market, compensation-related disposition, Butterfield directly holds 664,164 shares of Flywire common stock. The filing reflects routine tax withholding rather than an active decision to buy or sell shares in the market.
Flywire Corp General Counsel and CCO Peter Butterfield sold 1,480 shares of Voting Common Stock in an open-market transaction. The shares were sold on May 7, 2026 at a weighted average price of $18.016 per share, under a previously adopted Rule 10b5-1 trading plan. Following this sale, he directly holds 671,482 shares of Flywire common stock.
Flywire Corp Chief Executive Officer Michael Massaro reported open-market sales of 50,000 shares of Voting Common Stock. The transactions occurred on May 6, 2026 at weighted average prices of $16.6229 and $15.6543 per share, as part of two separate sale entries. The filing states these shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan. After the sales, Massaro directly holds 2,766,035 shares of Voting Common Stock. Indirect holdings reported in the filing are held by the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust, for which Massaro disclaims beneficial ownership except to the extent of any pecuniary interest.
Flywire Corp director Phillip John Riese reported an exercise-and-sell transaction in Voting Common Stock. On May 6, 2026, he sold a total of 37,921 shares in open-market trades at weighted average prices of $15.5374, $16.7334 and $17.5015, executed under a previously adopted Rule 10b5-1 trading plan.
On the same date, he exercised stock options to acquire 37,921 Voting Common Stock shares at an exercise price of $0.59 per share. Following these transactions, he holds 234,493 shares of Voting Common Stock directly and retains 53,000 stock options with a $0.59 exercise price expiring on December 14, 2026.
Flywire Corp Chief Financial Officer Cosmin Pitigoi executed an open-market sale of 35,000 shares of Voting Common Stock on May 6, 2026.
The shares were sold at a weighted average price of $17.3764 per share under a previously adopted Rule 10b5-1 trading plan. After this transaction, Pitigoi directly holds 897,138 shares of Flywire common stock.
Flywire Corp Chief Payments Officer Mohit Kansal reported an open-market sale of Voting Common Stock. On May 6, 2026, he sold 16,101 shares at $15.90 per share. After this transaction, he continues to hold 567,794 shares directly. The sale was carried out under a previously adopted Rule 10b5-1 trading plan, indicating it was pre-scheduled rather than a discretionary trade.
Flywire Corp Chief Financial Officer Cosmin Pitigoi reported an open-market sale of Voting Common Stock. On April 21, 2026, he sold 30,000 shares at $14.00 per share. After this transaction, he directly held 932,138 shares, indicating he retained a substantial remaining position.
Flywire Corp officer David R. King exercised employee stock options to acquire 8,000 shares of Voting Common Stock at $3.95 per share. The options were fully vested. After this exercise, he directly holds 1,100,680 shares of Flywire common stock.
An additional 276,204 shares are held by the D R King Revocable Trust Dated 10/05/07, reported as indirect ownership. King is a trustee of the trust but disclaims beneficial ownership of those shares except to the extent of any pecuniary interest.
Flywire Corp General Counsel and CCO Peter Butterfield exercised stock options covering 140,000 shares of Voting Common Stock at an exercise price of $0.59 per share on March 30, 2026. The option was fully vested, and following the exercise he directly holds 672,962 common shares, with no remaining derivative position from this option.
Katziff Christine reported acquisition or exercise transactions in this Form 4 filing.
Flywire Corp director Christine Katziff received an equity grant of 28,225 shares of Voting Common Stock in the form of restricted stock units. The award was granted at no cash cost to her and represents her entire reported direct holding after this transaction.
The RSUs vest in three equal annual installments following the grant date, as long as she continues providing service to Flywire through each vesting date. The award will fully vest earlier if there is a change in control of the company or upon her death or disability.
Flywire Corp Chief Executive Officer Michael Massaro exercised employee stock options to acquire 14,087 shares of Voting Common Stock at an exercise price of $3.95 per share. These options were fully vested, and the transaction reflects a derivative exercise rather than an open-market purchase.
Following the exercise, Massaro directly holds 2,816,035 shares of Flywire common stock. Additional holdings of 192,193 shares and 307,548 shares are held through family trusts where his spouse is trustee; he disclaims beneficial ownership of those shares except for any pecuniary interest. No open-market sales or tax-withholding dispositions were reported in this filing.
Flywire Corp General Counsel and Chief Compliance Officer Peter Butterfield sold 9,009 shares of Voting Common Stock in an open-market transaction. The sale occurred on March 5, 2026 at a weighted average price of $13.0473 per share, with individual trade prices ranging from $12.74 to $13.33. After this sale, Butterfield directly holds 532,962 shares of Flywire common stock.
Flywire Corp Chief Payments Officer Mohit Kansal reported a tax-related share disposition. On March 2, 2026, 20,181 shares of Voting Common Stock were withheld by Flywire to cover income tax obligations from the net settlement of restricted stock units, not through an open market sale. After this withholding, Kansal directly held 583,895 shares of Flywire common stock.
Flywire Corp’s Chief Executive Officer Michael Massaro reported several share transactions in Voting Common Stock. He conducted an open-market sale of 150,000 shares at a weighted average price of $12.3076 per share pursuant to a Rule 10b5-1 trading plan. In a separate transaction, 105,021 shares were withheld by the company to cover income tax obligations related to restricted stock unit settlements, which was not an open-market sale. Following these transactions, he reported continued direct ownership and additional indirect holdings through family trusts, for which he disclaims beneficial ownership except for any pecuniary interest.
Flywire Corp’s Chief Financial Officer, Cosmin Pitigoi, reported a tax-related stock transaction. On March 2, 2026, the company withheld 39,722 shares of Voting Common Stock at $12.43 per share to satisfy income tax obligations on vested restricted stock units.
The footnote explains this was a tax-withholding disposition and not an open market sale. After this withholding, Pitigoi’s direct holdings total 962,138 shares of Voting Common Stock, showing he continues to hold a substantial equity position in Flywire.
Flywire Corp Chief Technology Officer David R. King reported a tax-withholding disposition of 34,811 shares of Voting Common Stock at $12.43 per share on March 2, 2026. These shares were withheld by the issuer to satisfy income tax obligations tied to net-settled time-based restricted stock units and did not involve an open-market sale. After this, he held 1,092,680 shares directly. An additional 276,204 shares are held by the D R King Revocable Trust Dated 10/05/07, where he is trustee and disclaims beneficial ownership except for any pecuniary interest.