United States Professional & Commercial Services

Flywire Corp (FLYW)

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Over the past 90 days, Flywire Corp insiders have engaged in 37 transactions, all of which were sales totaling approximately $22.3 million. Key executives, including CEO Michael Massaro, have conducted significant planned sales. These transactions follow a positive earnings report in May, with the stock price currently trading at 66.54% of its 52-week range.
Ticker: FLYW Exchange: NSM
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• Purchase • Sale • Planned purchase • Planned sale Net purchase Net sale Buy signal Sell signal Earnings
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Trades
Planned sale 17 Jul 2026
Value US$2,352,145.55 | Price 211.41 | Shares 24,818 (+12.7%)
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value 		Number of shares Price Value Details
2026-07-20 2026-07-17 PlS Planned sale
4.0
Massaro Michael

Chief Executive Officer

Executive Director
24,818 +12.7%
211.41
US$2,352,146 		24,818 +12.7% 211.41 US$2,352,146
2026-07-20 2026-07-16 PlS Planned sale
4.0
Massaro Michael

Chief Executive Officer

Executive Director
17,648 -6.9%
465.99
US$2,962,112 		17,648 -6.9% 465.99 US$2,962,112
2026-07-06 2026-07-01 PlS Planned sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
81,226 -23.1%
418.38
US$1,689,606 		81,226 -23.1% 418.38 US$1,689,606
2026-07-01 2026-07-01 PrS Proposed sale
3.9
Peter T Butterfield

Officer

Officer
32,576
18.00
US$586,368 		32,576 18.00 US$586,368
2026-06-29 2026-06-25 PlS Planned sale
Kansal Mohit

Chief Payments Officer

Officer
3,650 -0.7%
16.96
US$61,904 		3,650 -0.7% 16.96 US$61,904
2026-06-25 2026-06-25 PrS Proposed sale
Kansal Mohit

Officer

Officer
3,650
16.96
US$61,904 		3,650 16.96 US$61,904
2026-06-17 2026-06-15 PlS Planned sale
Kansal Mohit

Chief Payments Officer

Officer
54,543 -9.8%
15.15
US$826,594 		54,543 -9.8% 15.15 US$826,594
2026-06-17 2026-06-15 PlS Planned sale
4.0
Massaro Michael

Chief Executive Officer

Executive Director
50,000 -1.8%
15.26
US$762,940 		50,000 -1.8% 15.26 US$762,940
2026-06-17 2026-06-15 PlS Planned sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
6,528 -1.0%
15.08
US$98,420 		6,528 -1.0% 15.08 US$98,420
2026-06-17 2026-06-15 PlS Planned sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
6,528 -1.0%
15.08
US$98,420 		6,528 -1.0% 15.08 US$98,420
2026-06-15 2026-06-15 PrS Proposed sale
4.0
Michael P. Massaro

Officer

Officer
287,500
15.31
US$4,401,625 		287,500 15.31 US$4,401,625
2026-06-15 2026-06-15 PrS Proposed sale
Kansal Mohit

Officer

Officer
54,543
15.15
US$826,591 		54,543 15.15 US$826,591
2026-06-10 2026-06-08 S Sale
3.3
Santos Edwin J
Non-Executive Director
6,524 -36.1%
14.12
US$92,123 		6,524 -36.1% 14.12 US$92,123
2026-06-08 2026-06-08 PrS Proposed sale
3.3
Santos Edwin J

Director

Non-Executive Director
6,524
14.12
US$92,123 		6,524 14.12 US$92,123
2026-06-09 2026-06-05 PlS Planned sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
6,188 -0.9%
14.40
US$89,113 		6,188 -0.9% 14.40 US$89,113
2026-06-09 2026-06-05 PlS Planned sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
6,188 -0.9%
14.40
US$89,113 		6,188 -0.9% 14.40 US$89,113
2026-06-05 2026-06-05 PrS Proposed sale
3.9
Peter T Butterfield

Officer

Officer
12,716
14.55
US$185,018 		12,716 14.55 US$185,018
2026-06-05 2026-06-05 PrS Proposed sale
3.9
Peter T Butterfield

Officer

Officer
12,716
14.55
US$185,018 		12,716 14.55 US$185,018
2026-06-08 2026-06-04 S Sale
3.3
Santos Edwin J
Non-Executive Director
10,466 -36.7%
14.69
US$153,714 		10,466 -36.7% 14.69 US$153,714
2026-06-04 2026-06-04 PrS Proposed sale
3.3
Santos Edwin J

Director

Non-Executive Director
10,466
14.69
US$153,714 		10,466 14.69 US$153,714
2026-06-04 2026-06-02 PlS Planned sale
3.8
Riese Phillip John
Non-Executive Director
200 -0.1%
16.18
US$3,236 		200 -0.1% 16.18 US$3,236
2026-06-04 2026-06-02 PlS Planned sale
3.8
Riese Phillip John
Non-Executive Director
4,800 -2.0%
15.39
US$73,894 		4,800 -2.0% 15.39 US$73,894
2026-06-02 2026-06-02 PrS Proposed sale
3.8
Riese Phillip John

Director

Non-Executive Director
5,000
16.35
US$81,750 		5,000 16.35 US$81,750
2026-06-03 2026-06-01 PlS Planned sale
3.4
Orgel Rob

President and COO

Officer
178,980 -15.7%
17.00
US$3,042,660 		178,980 -15.7% 17.00 US$3,042,660
2026-06-01 2026-06-01 PrS Proposed sale
3.4
Orgel Rob

Officer

Officer
178,980
17.00
US$3,042,660 		178,980 17.00 US$3,042,660
2026-05-11 2026-05-07 PlS Planned sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
1,480 -0.2%
18.02
US$26,664 		1,480 -0.2% 18.02 US$26,664
2026-05-07 2026-05-07 PrS Proposed sale
3.9
Peter T Butterfield

Affiliate
32,576
18.01
US$586,693 		32,576 18.01 US$586,693
2026-05-08 2026-05-06 PlS Planned sale
4.0
Massaro Michael

Chief Executive Officer

Executive Director
38,170 -1.4%
16.62
US$634,496 		38,170 -1.4% 16.62 US$634,496
2026-05-08 2026-05-06 PlS Planned sale
4.0
Massaro Michael

Chief Executive Officer

Executive Director
11,830 -0.4%
15.65
US$185,190 		11,830 -0.4% 15.65 US$185,190
2026-05-08 2026-05-06 PlS Planned sale
3.8
Riese Phillip John
Non-Executive Director
14,820 -5.9%
17.50
US$259,372 		14,820 -5.9% 17.50 US$259,372
2026-05-08 2026-05-06 PlS Planned sale
3.8
Riese Phillip John
Non-Executive Director
17,806 -6.7%
16.73
US$297,955 		17,806 -6.7% 16.73 US$297,955
2026-05-08 2026-05-06 PlS Planned sale
3.8
Riese Phillip John
Non-Executive Director
5,295 -1.9%
15.54
US$82,271 		5,295 -1.9% 15.54 US$82,271
2026-05-08 2026-05-06 PlS Planned sale
Pitigoi Cosmin

Chief Financial Officer

Officer
35,000 -3.8%
17.38
US$608,174 		35,000 -3.8% 17.38 US$608,174
2026-05-08 2026-05-06 PlS Planned sale
Kansal Mohit

Chief Payments Officer

Officer
16,101 -2.8%
15.90
US$256,006 		16,101 -2.8% 15.90 US$256,006
2026-05-06 2026-05-06 PrS Proposed sale
Pitigoi Cosmin

Officer

Officer
35,000
17.38
US$608,174 		35,000 17.38 US$608,174
2026-05-06 2026-05-06 PrS Proposed sale
3.8
Riese Phillip John

Director

Non-Executive Director
37,921
16.87
US$639,598 		37,921 16.87 US$639,598
2026-05-06 2026-05-06 PrS Proposed sale
Kansal Mohit

Officer

Officer
16,101
15.90
US$256,006 		16,101 15.90 US$256,006
2026-04-23 2026-04-21 S Sale
Pitigoi Cosmin

Chief Financial Officer

Officer
30,000 -3.1%
14.00
US$420,000 		30,000 -3.1% 14.00 US$420,000
2026-04-21 2026-04-21 PrS Proposed sale
Pitigoi Cosmin

Officer

Officer
30,000
14.00
US$420,000 		30,000 14.00 US$420,000
2026-03-09 2026-03-05 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
9,009 -1.7%
13.05
US$117,543 		9,009 -1.7% 13.05 US$117,543
2026-03-05 2026-03-05 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
9,009
12.85
US$115,765 		9,009 12.85 US$115,765
2026-03-04 2026-03-02 PlS Planned sale
4.0
Massaro Michael

Chief Executive Officer

Executive Director
150,000 -4.9%
12.31
US$1,846,140 		150,000 -4.9% 12.31 US$1,846,140
2026-03-02 2026-03-02 PrS Proposed sale
4.0
Michael P. Massaro

Officer

Officer
262,500
12.43
US$3,262,875 		262,500 12.43 US$3,262,875
2026-02-18 2026-02-13 B Purchase
1.4
Voss Capital, LP
Large shareholder
25,000 +1.1%
10.99
US$274,795 		25,000 +1.1% 10.99 US$274,795
2026-01-09 2026-01-07 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
13,327 -3.4%
15.01
US$200,073 		13,327 -3.4% 15.01 US$200,073
2026-01-09 2026-01-07 S Sale
3.8
Riese Phillip John
Non-Executive Director
16,612 -6.6%
15.08
US$250,559 		16,612 -6.6% 15.08 US$250,559
2026-01-07 2026-01-07 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
13,327
15.00
US$199,905 		13,327 15.00 US$199,905
2026-01-07 2026-01-07 PrS Proposed sale
3.8
Riese Phillip John

Director

Non-Executive Director
16,612
15.08
US$250,559 		16,612 15.08 US$250,559
2026-01-07 2025-12-31 B Purchase
1.4
Voss Capital, LP
Large shareholder
44,991 +0.5%
14.23
US$640,415 		44,991 +0.5% 14.23 US$640,415
2026-01-07 2025-12-30 B Purchase
1.4
Voss Capital, LP
Large shareholder
181,121 +1.9%
14.15
US$2,562,862 		181,121 +1.9% 14.15 US$2,562,862
2025-12-30 2025-12-23 PlS Planned sale
3.8
Riese Phillip John
Non-Executive Director
367 -0.2%
15.00
US$5,505 		367 -0.2% 15.00 US$5,505
2025-12-23 2025-12-23 PrS Proposed sale
3.8
Riese Phillip John

Director

Non-Executive Director
367
15.00
US$5,505 		367 15.00 US$5,505
2025-12-11 2025-12-09 PlS Planned sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
8,120 -2.1%
13.69
US$111,159 		8,120 -2.1% 13.69 US$111,159
2025-12-09 2025-12-09 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
8,120
13.74
US$111,569 		8,120 13.74 US$111,569
2025-12-30 2025-11-05 PlS Planned sale
3.8
Riese Phillip John
Non-Executive Director
100 -0.0%
15.02
US$1,502 		100 -0.0% 15.02 US$1,502
2025-11-07 2025-11-05 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
1,000 -0.3%
15.00
US$15,000 		1,000 -0.3% 15.00 US$15,000
2025-11-05 2025-11-05 PrS Proposed sale
3.8
Riese Phillip John

Director

Non-Executive Director
100
15.02
US$1,502 		100 15.02 US$1,502
2025-09-10 2025-09-08 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
9,563 -2.4%
13.15
US$125,706 		9,563 -2.4% 13.15 US$125,706
2025-09-08 2025-09-08 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
23,890
12.99
US$310,331 		23,890 12.99 US$310,331
2025-06-11 2025-06-09 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
9,563 -2.3%
10.27
US$98,212 		9,563 -2.3% 10.27 US$98,212
2025-06-09 2025-06-09 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
23,890
10.50
US$250,845 		23,890 10.50 US$250,845
2025-06-09 2025-06-06 S Sale
3.3
Santos Edwin J
Non-Executive Director
5,000 -22.7%
10.50
US$52,500 		5,000 -22.7% 10.50 US$52,500
2025-06-06 2025-06-06 PrS Proposed sale
3.3
Santos Edwin J

Director

Non-Executive Director
5,000
10.50
US$52,500 		5,000 10.50 US$52,500
2025-06-09 2025-06-05 S Sale
3.3
Santos Edwin J
Non-Executive Director
5,466 -19.9%
10.04
US$54,879 		5,466 -19.9% 10.04 US$54,879
2025-06-05 2025-06-05 PrS Proposed sale
3.3
Santos Edwin J

Director

Non-Executive Director
5,466
10.04
US$54,880 		5,466 10.04 US$54,880
2025-06-05 2025-06-05 PrS Proposed sale
2.5
Harris Matthew C

Director

Non-Executive Director
4,274
10.13
US$43,279 		4,274 10.13 US$43,279
2025-03-12 2025-03-10 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
5,523 -2.2%
10.08
US$55,667 		5,523 -2.2% 10.08 US$55,667
2025-03-10 2025-03-10 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
19,850
10.19
US$202,272 		19,850 10.19 US$202,272
2025-03-03 2025-02-27 B Purchase
1.5
Howard Gretchen
Non-Executive Director
8,889 +40.6%
10.94
US$97,238 		8,889 +40.6% 10.94 US$97,238
2024-12-12 2024-12-10 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
4,760 -1.8%
20.68
US$98,449 		4,760 -1.8% 20.68 US$98,449
2024-12-10 2024-12-10 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
4,760
20.86
US$99,294 		4,760 20.86 US$99,294
2024-09-11 2024-09-09 S Sale
3.9
Butterfield Peter

General Counsel and CCO

Officer
4,747 -1.7%
17.29
US$82,092 		4,747 -1.7% 17.29 US$82,092
2024-09-09 2024-09-09 PrS Proposed sale
3.9
Peter Butterfield

Officer

Officer
4,747
17.29
US$82,092 		4,747 17.29 US$82,092
2024-09-09 2024-09-05 S Sale
3.4
Orgel Rob

President and COO

Officer
3,824 -0.8%
17.31
US$66,209 		3,824 -0.8% 17.31 US$66,209
2024-09-09 2024-09-05 S Sale
3.5
King David R.

Chief Technology Officer

Officer
3,504 -0.6%
17.31
US$60,668 		3,504 -0.6% 17.31 US$60,668
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