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Insider Cluster (3 insiders) ·Filed Sep 10, 2026

FLYW

Flywire Corp
BEARISH
Impact 5/10
Horizonweeks Processed1mo ago
Insider cluster: 3 insiders, $2.5M total
Actionable Insight ▼ Bearish

The CEO's $2.07M open-market sale is the most significant element, as C-suite sales carry more weight. However, the total value is modest relative to market cap, and insider sales are often liquidity-driven. Monitor for any upcoming earnings release or material news that could explain the timing.

DirectionBearish
Confidencemedium
Horizonweeks
Latest settled — T+1d
FLYW ▲ +0.68% at T+1d
SHORT call ✗ call lost -0.68% · α vs SPY +0.18% · entry $17.75 → $17.87
Next anchor: T+5d due 6w ago
Entry = T+0 close
Sep 9, 2026
via day close
T+1d
+0.68%
call -0.68% · α +0.18%
$17.87
settled 7w ago
T+5d
Pending
due 6w ago
T+20d
Pending
due 20d ago
T+60d
Pending
in 5w

Price Chart

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Executive Summary

Flywire Corp insiders, including CEO Michael Massaro, sold a total of $2.52M in shares over a 7-day window. The CEO's $2.07M sale dominates the cluster, representing ~0.11% of the company's $2.2B market cap. While the dollar amount is modest relative to market cap, the CEO's open-market sale alongside other senior executives is a notable signal, though insider sales are generally less predictive than buys per academic literature.

Key Financial Metrics

Direction
selling
Total Value
$2.5M
Insiders
3

Key Facts

  • CEO Michael Massaro sold 112,500 shares for $2.07M on 2026-09-01
  • General Counsel Peter Butterfield sold 12,156 shares for $219K on 2026-09-08
  • Chief Payments Officer Mohit Kansal sold 12,400 shares for $232K on 2026-09-02
  • Total insider sales of $2.52M represent ~0.11% of Flywire's $2.2B market cap
  • All three sales were open-market transactions, not 10b5-1 plan sales

Financial Impact

Total insider sales of $2.52M, representing 0.11% of market cap

insider ownershipmarket sentiment

Risk Factors

  • CEO sale could signal lack of confidence in near-term prospects
  • Cluster of multiple senior executives selling in a short window raises coordination concerns
  • Sales are small relative to market cap, limiting bearish conviction

Market Snapshot

Exchange
Nasdaq
Sector
Services-Business Services, NEC
Analyst Consensus
62% bullish (21 analysts)

Investment Themes

Software & IT

Documents Analyzed

This report is based on 1 SEC document filed with EDGAR.

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-FLYW-1789106964565
25 reports for FLYW
Performance horizon
75% Hit rate @ T+60 3 of 4 directional calls Went positive at some point 8 of 9 best @ T+60▲ +27.08%Feb 24, 2026
Filters
Rows
Reports for FLYW — sortable, filterable
TypeNow
Oct 22, 2026
4d ago
Press Release
NEUTRAL ★ 3/10
$19.15awaiting T+60—$19.40 (+1.31%)
Sep 15, 2026
5w ago
Insider Cluster
NEUTRAL ★ 5/10
$17.80awaiting T+60—$19.40 (+8.99%)
Sep 10, 2026
6w ago
Insider Cluster
BEARISH ★ 5/10
$17.75awaiting T+60—$19.40 (−9.30%)
Sep 3, 2026
7w ago
Insider Cluster
BEARISH ★ 5/10
$18.55awaiting T+60—$19.40 (−4.58%)
Aug 19, 2026
9w ago
Press Release
NEUTRAL ★ 4/10
$18.83awaiting T+60—$19.40 (+3.03%)
Aug 12, 2026
10w ago
Press Release
NEUTRAL ★ 3/10
$17.46awaiting T+60—$19.40 (+11.11%)
Aug 7, 2026
11w ago
144
NEUTRAL ★ 2/10
$17.78awaiting T+60—$19.40 (+9.11%)
Jul 6, 2026
16w ago
Insider Cluster
NEUTRAL ★ 2/10
$18.55 $17.50▼ −5.66%▼ −7.66%$19.40 (+4.58%)
Jun 26, 2026
17w ago
Institutional Cluster
MIXED ★ 4/10
$17.54 $17.13▼ −2.37%▼ −6.85%$19.40 (+10.60%)
Jun 17, 2026
18w ago
Insider Cluster
BEARISH ★ 6/10
$15.85awaiting T+60—$19.40 (−22.40%)
Showing 10 of 25

US Market Status

Market Closed — Opens Wed (12h 49m)

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Report published Sep 11, 2026