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Flywire Corp

FLYW Net selling
CIK 0001580560 #1943 in the set updated 17 Sep 2026
Bought (120 mo)
$3.58M
out of their own pocket, the only kind of buying there is
Sold (120 mo)
$4.87B
$19.53M on a plan · $221.58M straight out of an exercise
Sold at will
$4.63B
294 of 525 sales
Net
−$4.86B
−$4.62B against sales at will

By person

26 insiders · 573 transactions
119×

Michael Massaro holds 119 times base salary in stock. $54.00M of shares against $450.00K in salary for 2025.

Salary from the company's own proxy. The shares are what Michael Massaro last reported holding, valued at $17.88, the price Voting Common Stock was last bought or sold at on the open market here, on 11 Sep 2026.

Insider
Role
Bought
Sold
Net
Holding
Of company
Worth
Change
Massaro Michael
Chief Executive Officer
—
$3.80B (126)
−$3.80B
3,020,299
2.48%
$54.00M
+70.5%
BAIN CAPITAL VENTURE INVESTORS, LLC entity
10% owner
—
$304.64M (8)
−$304.64M
25,335,252
20.83%
$452.96M
+24.4%
Harris Matthew C
Director
—
$195.53M (8)
−$195.53M
16,578,878
13.63%
$296.41M
−27.5%
Natauri Jo
Director
—
$163.82M (71) scheduled
−$163.82M
3,483,195
2.86%
$62.28M
0.0%
GOLDMAN SACHS GROUP INC entity
Director
—
$162.80M (71) scheduled
−$162.80M
3,483,195
2.86%
$62.28M
+1.1%
Agarwal Ajay
10% owner
—
$86.80M (3)
−$86.80M
8,795,388
7.23%
$157.25M
−35.7%
Salem Enrique T
10% owner
—
$86.08M (2)
−$86.08M
8,795,388
7.23%
$157.25M
−35.5%
Orgel Rob
President and COO
—
$16.75M (41) scheduled
−$16.75M
991,918
0.8157%
$17.73M
+535.4%
King David R.
See Remarks
—
$13.92M (35)
−$13.92M
1,591,187
1.31%
$28.45M
+19.6%
Ellis Michael G
Chief Financial Officer
—
$9.27M (40) scheduled
−$9.27M
367,318
0.3020%
$6.57M
+258.7%
Butterfield Peter
General Counsel and CCO
—
$7.52M (53) scheduled
−$7.52M
601,022
0.4942%
$10.75M
+15,311%
Voss Capital, LP entity
10% owner
$3.48M (3)
$10.34M (17)
−$6.86M
24,917,497
20.49%
$445.49M
−1.2%
Riese Phillip John
Director
—
$6.47M (34)
−$6.47M
258,051
0.2122%
$4.61M
—
Finkelstein Alex
Director
—
$1.75M (2)
−$1.75M
15,171,012
12.48%
$271.24M
−3.3%
Kansal Mohit
Chief Payments Officer
—
$1.38M (4) scheduled
−$1.38M
478,324
0.3933%
$8.55M
−20.9%
Santos Edwin J
Director
—
$1.07M (8)
−$1.07M
11,558
0.0095%
$206.64K
—
Pitigoi Cosmin
Chief Financial Officer
—
$1.03M (2) scheduled
−$1.03M
856,575
0.7044%
$15.31M
—
Howard Gretchen
Director
$97.24K (1)
—
+$97.24K
59,318
0.0488%
$1.06M
—
Spark Management Partners II, LLC entity
10% owner
—
—
—
14,917,797
12.27%
$266.71M
+54.3%
FMR LLC entity
See Remark 1
—
—
—
7,460,328
6.13%
$133.38M
+3,789%
Ossa Investments Pte. Ltd. entity
10% owner
—
—
—
1,873,320
1.54%
$33.49M
—
Blanc Patrick
Chief Technology Officer
—
—
—
234,234
0.1926%
$4.19M
—
Offereins Diane E
Director
—
—
—
58,777
0.0483%
$1.05M
—
Jaques Carleigh
Director
—
—
—
44,152
0.0363%
$789.38K
—
Katziff Christine
Director
—
—
—
39,783
0.0327%
$711.27K
—
Hao Yvonne
Director
—
—
—
16,363
0.0135%
$292.55K
—

Individual transactions

129
Insider
Date
Role
Action
Shares
Price
Amount
Voss Capital, LP
28 Aug 2026
10% owner
Sell indirect
7,763
$18.78
$145.81K
Voss Capital, LP
28 Aug 2026
10% owner
Sell indirect
37,005
$18.78
$695.04K
Voss Capital, LP
27 Aug 2026
10% owner
Sell indirect
91,931
$18.92
$1.74M
Voss Capital, LP
27 Aug 2026
10% owner
Sell indirect
1,996
$18.91
$37.75K
Voss Capital, LP
26 Aug 2026
10% owner
Sell indirect
25,539
$18.99
$485.11K
Voss Capital, LP
26 Aug 2026
10% owner
Sell indirect
555
$18.99
$10.54K
Voss Capital, LP
25 Aug 2026
10% owner
Sell indirect
169,295
$19.19
$3.25M
Voss Capital, LP
25 Aug 2026
10% owner
Sell indirect
3,678
$19.19
$70.60K
Voss Capital, LP
24 Aug 2026
10% owner
Sell indirect
99,146
$19.49
$1.93M
Voss Capital, LP
24 Aug 2026
10% owner
Sell indirect
2,154
$19.49
$41.98K
Voss Capital, LP
19 Aug 2026
10% owner
Sell indirect
25,000
$18.86
$471.49K
Voss Capital, LP
18 Aug 2026
10% owner
Sell indirect
18,553
$18.40
$341.30K
Voss Capital, LP
18 Aug 2026
10% owner
Sell indirect
10,947
$18.24
$199.64K
Voss Capital, LP
18 Aug 2026
10% owner
Sell indirect
15,724
$18.40
$289.26K
Voss Capital, LP
18 Aug 2026
10% owner
Sell indirect
15,723
$18.40
$289.24K
Voss Capital, LP
18 Aug 2026
10% owner
Sell indirect
9,276
$18.24
$169.16K
Voss Capital, LP
18 Aug 2026
10% owner
Sell indirect
9,277
$18.24
$169.18K
Santos Edwin J
8 Jun 2026
Director
Sell
6,524
$14.12
$92.12K
Santos Edwin J
4 Jun 2026
Director
Sell
10,466
$14.69
$153.71K
Santos Edwin J
6 Jun 2025
Director
Sell
5,000
$10.50
$52.50K
Santos Edwin J
5 Jun 2025
Director
Sell
5,466
$10.04
$54.88K
Massaro Michael
5 Sep 2024
Chief Executive Officer
Sell
7,646
$17.31
$132.38K
Orgel Rob
5 Sep 2024
President and COO
Sell
3,824
$17.31
$66.21K
King David R.
5 Sep 2024
Chief Technology Officer
Sell
3,504
$17.31
$60.67K
Butterfield Peter
5 Sep 2024
General Counsel and CCO
Sell
1,335
$17.31
$23.11K
Orgel Rob
3 Sep 2024
President and COO
Sell
4,552
$18.04
$82.13K
Butterfield Peter
3 Sep 2024
General Counsel and CCO
Sell
1,769
$18.04
$31.92K
King David R.
3 Sep 2024
Chief Technology Officer
Sell
3,353
$18.04
$60.50K
Massaro Michael
3 Sep 2024
Chief Executive Officer
Sell
8,629
$18.04
$155.69K
Santos Edwin J
8 Aug 2024
Director
Sell
10,448
$18.58
$194.14K
Massaro Michael
5 Jun 2024
Chief Executive Officer
Sell
7,631
$16.69
$127.37K
Orgel Rob
5 Jun 2024
President and COO
Sell
3,815
$16.69
$63.68K
King David R.
5 Jun 2024
Chief Technology Officer
Sell
3,496
$16.69
$58.35K
Butterfield Peter
5 Jun 2024
General Counsel and CCO
Sell
824
$16.69
$13.75K
Butterfield Peter
3 Jun 2024
General Counsel and CCO
Sell
1,104
$16.95
$18.71K
Orgel Rob
3 Jun 2024
President and COO
Sell
4,589
$16.95
$77.78K
Massaro Michael
3 Jun 2024
Chief Executive Officer
Sell
8,698
$16.95
$147.42K
King David R.
3 Jun 2024
Chief Technology Officer
Sell
3,381
$16.95
$57.30K
Riese Phillip John
13 Mar 2024
Director
Sell
25,000
$26.21
$655.14K
Riese Phillip John
12 Mar 2024
Director
Sell
50,000
$26.41
$1.32M
Riese Phillip John
11 Mar 2024
Director
Sell
841
$27.01
$22.71K
Riese Phillip John
11 Mar 2024
Director
Sell
49,159
$26.35
$1.30M
Massaro Michael
5 Mar 2024
Chief Executive Officer
Sell
7,644
$27.18
$207.73K
Butterfield Peter
5 Mar 2024
General Counsel and CCO
Sell
825
$27.18
$22.42K
King David R.
5 Mar 2024
Chief Technology Officer
Sell
3,502
$27.18
$95.17K
Orgel Rob
5 Mar 2024
President and COO
Sell
3,822
$27.18
$103.86K
Massaro Michael
4 Mar 2024
Chief Executive Officer
Sell
28,822
$27.30
$786.84K
Butterfield Peter
4 Mar 2024
General Counsel and CCO
Sell
4,730
$27.30
$129.13K
King David R.
4 Mar 2024
Chief Technology Officer
Sell
9,366
$27.30
$255.69K
Orgel Rob
4 Mar 2024
President and COO
Sell
17,150
$27.30
$468.20K
Butterfield Peter
5 Dec 2023
General Counsel and CCO
Sell
1,339
$23.40
$31.34K
Massaro Michael
5 Dec 2023
Chief Executive Officer
Sell
7,679
$23.40
$179.70K
King David R.
5 Dec 2023
Chief Technology Officer
Sell
3,518
$23.40
$82.33K
Orgel Rob
5 Dec 2023
President and COO
Sell
3,839
$23.40
$89.84K
Massaro Michael
18 Oct 2023
Chief Executive Officer
Sell
10,749
$29.03
$311.99K
Massaro Michael
17 Oct 2023
Chief Executive Officer
Sell
11,457
$29.00
$332.20K
Massaro Michael
5 Oct 2023
Chief Executive Officer
Sell
11,457
$29.76
$340.92K
Massaro Michael
4 Oct 2023
Chief Executive Officer
Sell
600
$30.30
$18.18K
Massaro Michael
4 Oct 2023
Chief Executive Officer
Sell
10,857
$29.38
$318.95K
Massaro Michael
19 Sep 2023
Chief Executive Officer
Sell
11,457
$30.20
$346.00K
Massaro Michael
18 Sep 2023
Chief Executive Officer
Sell
11,457
$30.93
$354.33K
Massaro Michael
6 Sep 2023
Chief Executive Officer
Sell
11,457
$33.40
$382.69K
King David R.
5 Sep 2023
Chief Technology Officer
Sell
3,548
$33.75
$119.74K
Massaro Michael
5 Sep 2023
Chief Executive Officer
Sell
11,457
$33.82
$387.46K
Massaro Michael
5 Sep 2023
Chief Executive Officer
Sell
7,742
$33.75
$261.28K
Massaro Michael
30 Aug 2023
Chief Executive Officer
Sell
11,457
$32.99
$377.92K
Massaro Michael
29 Aug 2023
Chief Executive Officer
Sell
11,457
$31.95
$366.02K
Massaro Michael
18 Aug 2023
Chief Executive Officer
Sell
11,457
$30.27
$346.81K
Massaro Michael
17 Aug 2023
Chief Executive Officer
Sell
11,457
$30.70
$351.77K
King David R.
9 Aug 2023
Chief Technology Officer
Sell indirect
2,450
$35.55
$87.10K
King David R.
17 Jul 2023
Chief Technology Officer
Sell indirect
50,000
$33.55
$1.68M
Massaro Michael
13 Jul 2023
Chief Executive Officer
Sell
11,457
$30.96
$354.67K
Massaro Michael
12 Jul 2023
Chief Executive Officer
Sell
11,457
$29.84
$341.92K
Massaro Michael
5 Jul 2023
Chief Executive Officer
Sell
11,457
$29.93
$342.91K
Massaro Michael
3 Jul 2023
Chief Executive Officer
Sell
11,457
$30.92
$354.30K
Harris Matthew C
16 Jun 2023
Director
Sell indirect
50,410
$31.86
$1.61M
Harris Matthew C
16 Jun 2023
Director
Sell indirect
191,976
$30.98
$5.95M
Massaro Michael
14 Jun 2023
Chief Executive Officer
Sell
11,457
$31.26
$358.20K
Massaro Michael
13 Jun 2023
Chief Executive Officer
Sell
11,457
$32.31
$370.22K
King David R.
13 Jun 2023
Chief Technology Officer
Sell indirect
47,804
$32.53
$1.55M
King David R.
12 Jun 2023
Chief Technology Officer
Sell indirect
1,200
$32.51
$39.01K
King David R.
9 Jun 2023
Chief Technology Officer
Sell indirect
996
$32.51
$32.38K
Massaro Michael
6 Jun 2023
Chief Executive Officer
Sell
11,457
$31.18
$357.26K
Santos Edwin J
5 Jun 2023
Director
Sell
4,861
$30.99
$150.64K
Massaro Michael
5 Jun 2023
Chief Executive Officer
Sell
11,457
$31.04
$355.60K
Ellis Michael G
5 Jun 2023
Chief Financial Officer
Sell
2,216
$31.30
$69.37K
King David R.
5 Jun 2023
Chief Technology Officer
Sell
3,111
$31.30
$97.38K
Orgel Rob
5 Jun 2023
President and COO
Sell
3,811
$31.30
$119.30K
Butterfield Peter
5 Jun 2023
General Counsel and CCO
Sell
1,329
$31.30
$41.60K
Massaro Michael
5 Jun 2023
Chief Executive Officer
Sell
7,622
$31.30
$238.59K
Santos Edwin J
1 Jun 2023
Director
Sell
9,062
$30.49
$276.32K
Massaro Michael
31 May 2023
Chief Executive Officer
Sell
11,457
$29.30
$335.75K
Massaro Michael
30 May 2023
Chief Executive Officer
Sell
11,457
$29.66
$339.87K
Harris Matthew C
26 May 2023
Director
Sell indirect
169,716
$29.81
$5.06M
King David R.
23 May 2023
Chief Technology Officer
Sell indirect
26,053
$31.76
$827.49K
King David R.
22 May 2023
Chief Technology Officer
Sell indirect
13,947
$31.51
$439.41K
Harris Matthew C
18 May 2023
Director
Sell indirect
1,000,000
$30.60
$30.60M
Massaro Michael
17 May 2023
Chief Executive Officer
Sell
11,457
$28.85
$330.56K
Massaro Michael
16 May 2023
Chief Executive Officer
Sell
11,457
$30.54
$349.88K
King David R.
15 May 2023
Chief Technology Officer
Sell indirect
35,375
$30.55
$1.08M
Finkelstein Alex
11 May 2023
Director
Sell
34,060
$29.50
$1.00M
Harris Matthew C
11 May 2023
Director
Sell indirect
2,850,000
$29.51
$84.10M
Agarwal Ajay
11 May 2023
10% owner
Sell indirect
2,850,000
$29.51
$84.10M
Salem Enrique T
11 May 2023
10% owner
Sell indirect
2,850,000
$29.51
$84.10M
BAIN CAPITAL VENTURE INVESTORS, LLC
11 May 2023
10% owner
Sell indirect
2,850,000
$29.51
$84.10M
BAIN CAPITAL VENTURE INVESTORS, LLC
11 May 2023
10% owner
Sell indirect
2,850,000
$29.51
$84.10M
King David R.
10 May 2023
Chief Technology Officer
Sell indirect
4,625
$30.59
$141.49K
King David R.
13 Apr 2023
Chief Technology Officer
Sell indirect
5,016
$29.63
$148.61K
Massaro Michael
12 Apr 2023
Chief Executive Officer
Sell
11,457
$29.27
$335.31K
King David R.
12 Apr 2023
Chief Technology Officer
Sell indirect
2,295
$29.52
$67.74K
Massaro Michael
11 Apr 2023
Chief Executive Officer
Sell
50
$29.27
$1.46K
Massaro Michael
11 Apr 2023
Chief Executive Officer
Sell
25,740
$28.70
$738.70K
Massaro Michael
4 Apr 2023
Chief Executive Officer
Sell
19,033
$29.11
$553.97K
Massaro Michael
3 Apr 2023
Chief Executive Officer
Sell
27,138
$29.11
$789.92K
King David R.
31 Mar 2023
Chief Technology Officer
Sell
30,889
$29.55
$912.87K
King David R.
30 Mar 2023
Chief Technology Officer
Sell
1,800
$29.53
$53.15K
Massaro Michael
29 Mar 2023
Chief Executive Officer
Sell
2,000
$29.04
$58.08K
Massaro Michael
29 Mar 2023
Chief Executive Officer
Sell
8,332
$27.99
$233.24K
Massaro Michael
28 Mar 2023
Chief Executive Officer
Sell
24,296
$27.31
$663.54K
Orgel Rob
15 Mar 2023
President and COO
Sell
2,736
$26.80
$73.31K
Orgel Rob
15 Mar 2023
President and COO
Sell
14,439
$26.13
$377.28K
Massaro Michael
14 Mar 2023
Chief Executive Officer
Sell
22,013
$26.31
$579.12K
Massaro Michael
14 Mar 2023
Chief Executive Officer
Sell
700
$27.00
$18.90K
Massaro Michael
14 Mar 2023
Chief Executive Officer
Sell
4,166
$25.80
$107.50K
Ellis Michael G
14 Mar 2023
Chief Financial Officer
Sell
6,480
$26.31
$170.48K
Orgel Rob
14 Mar 2023
President and COO
Sell
14,329
$26.31
$376.97K
King David R.
14 Mar 2023
Chief Technology Officer
Sell
8,985
$26.31
$236.38K
Massaro Michael
13 Mar 2023
Chief Executive Officer
Sell
4,166
$24.04
$100.14K
Butterfield Peter
13 Mar 2023
General Counsel and CCO
Sell
9,856
$24.06
$237.11K
Showing 250 of 573 transactions. The figures above use every one of them.

What was left out

Form 4 filings counted 441
Amendments (4/A) skipped 8
Filings about a different issuer 0
Unreadable filings 0
Joint filings 57
Sales on a Rule 10b5-1 plan 42
Sales straight out of an exercise 189
Sales at will 294
Transactions with no price 0
Shares from compensation/vesting 370,206,368
Sales filed before the plan box existed 175
History held since 28 May 2021