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Insider Cluster (2 insiders) ·Filed Jun 17, 2026

FLYW

Flywire Corp
BEARISH
Impact 6/10
Horizonweeks Processed4mo ago
Insider cluster: 2 insiders, $855K total
Actionable Insight ▼ Bearish

The CEO and top legal officer both sold on the same day, which is a strong signal of potential near-term headwinds. Monitor for any 8-K filings, earnings pre-announcements, or guidance changes in the next 2-4 weeks. The cross-filing amplifiers (cluster-earnings-context, cluster-offering-context) suggest this selling may be followed by a capital raise or earnings miss.

DirectionBearish
Confidencemedium
Horizonweeks
Latest settled — T+20d
FLYW ▲ +17.92% at T+20d
SHORT call ✗ call lost -17.92% · α vs SPY -17.39% · entry $15.85 → $18.69
Next anchor: T+60d due 6w ago
Entry = T+0 close
Jun 17, 2026
via day close
T+1d
-2.65%
call +2.65% · α +2.34%
$15.43
settled 4mo ago
T+5d
+6.50%
call -6.50% · α -8.16%
$16.88
settled 4mo ago
T+20d
+17.92%
call -17.92% · α -17.39%
$18.69
settled 3mo ago
T+60d
Pending
due 6w ago

Price Chart

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Executive Summary

Flywire Corp's CEO and General Counsel sold a combined $855K in open-market shares within a 7-day window, with the CEO alone accounting for $763K. The selling is material relative to the $1.9B market cap (0.045%) but not large enough to be highly material; however, the cluster of two C-suite executives selling at similar times is notable.

Key Financial Metrics

Direction
selling
Total Value
$861.4K
Insiders
2

Key Facts

  • CEO Michael Massaro sold 50,000 shares at $15.26 for $763K on 2026-06-15
  • General Counsel Peter Butterfield sold 6,528 shares at $15.08 for $98K on 2026-06-15
  • Total open-market sales: $861K over 7 days
  • Sales represent 0.045% of $1.9B market cap
  • No insider purchases in the cluster window

Financial Impact

0.045% of market cap ($861K) in open-market sales by CEO and General Counsel

insider ownershipmarket sentiment

Risk Factors

  • Potential upcoming earnings miss or guidance cut
  • Possible secondary offering (dilution) given the cross-filing amplifier with offering-context
  • Insider sales may accelerate if the stock continues to decline

Market Snapshot

Exchange
Nasdaq
Sector
Services-Business Services, NEC
Analyst Consensus
71% 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-1781727340908
26 reports for FLYW
Performance horizon
75% Hit rate @ T+60 3 of 4 directional calls Went positive at some point 7 of 9 best @ T+60▲ +27.08%Feb 24, 2026
Filters
Rows
Reports for FLYW — sortable, filterable
TypeNow
Oct 27, 2026
today
SC 13G/A
NEUTRAL ★ 3/10
$19.16awaiting T+60—$18.84 (−1.67%)
Oct 22, 2026
5d ago
Press Release
NEUTRAL ★ 3/10
$19.15awaiting T+60—$18.84 (−1.62%)
Sep 15, 2026
6w ago
Insider Cluster
NEUTRAL ★ 5/10
$17.80awaiting T+60—$18.84 (+5.84%)
Sep 10, 2026
6w ago
Insider Cluster
BEARISH ★ 5/10
$17.75awaiting T+60—$18.84 (−6.14%)
Sep 3, 2026
7w ago
Insider Cluster
BEARISH ★ 5/10
$18.55awaiting T+60—$18.84 (−1.56%)
Aug 19, 2026
9w ago
Press Release
NEUTRAL ★ 4/10
$18.83awaiting T+60—$18.84 (+0.05%)
Aug 12, 2026
10w ago
Press Release
NEUTRAL ★ 3/10
$17.46awaiting T+60—$18.84 (+7.90%)
Aug 7, 2026
11w ago
144
NEUTRAL ★ 2/10
$17.78awaiting T+60—$18.84 (+5.96%)
Jul 6, 2026
16w ago
Insider Cluster
NEUTRAL ★ 2/10
$18.55 $17.50▼ −5.66%▼ −7.66%$18.84 (+1.56%)
Jun 26, 2026
17w ago
Institutional Cluster
MIXED ★ 4/10
$17.54 $17.13▼ −2.37%▼ −6.85%$18.84 (+7.41%)
Showing 10 of 26

US Market Status

Market Closed — Opens Wed (< 1m)

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Report published Jun 17, 2026