FLYW Flywire Corp
Price Chart
Executive Summary
Flywire Corp (FLYW) insiders sold a net $3.12M in open-market transactions over the past week, dominated by President & COO Rob Orgel's $3.04M sale at $17/share. Six directors received non-cash stock grants, and multiple C-suite executives surrendered shares for tax withholding on June 1, suggesting a vesting event. The open-market sales represent ~0.17% of market cap, a modest but notable amount, and the cluster is amplified by the COO's large sale alongside tax-driven surrenders by the CEO, CFO, and other officers.
Key Financial Metrics
Actionable Insight
The COO's $3M open-market sale is the largest insider sale at FLYW in the past 30 days and is not part of a routine 10b5-1 pattern (no prior regular sales visible). Combined with broad C-suite tax surrenders on the same date, this suggests a vesting event, but the COO's incremental cash-out above tax needs is a bearish signal. Monitor for any 8-K or press release in the next 2 weeks that could explain the timing. Historical calibration on FLYW warns that past bullish calls have been wrong — this cluster should be taken seriously as a potential negative signal.
Key Facts
- President & COO Rob Orgel sold 178,980 shares for $3.04M on June 1 at $17.00/share
- Director Riese Phillip John sold 4,800 shares for $73,894 on June 2 at $15.39/share
- CEO Michael Massaro surrendered 39,799 shares for tax withholding ($661K), CFO Cosmin Pitigoi surrendered 18,890 shares ($314K)
- Six directors received non-cash grants of 11,558 shares each on June 2
- Total open-market sales: $3.12M, representing ~0.17% of FLYW's $1.8B market cap
- Historical calibration shows past bullish/long calls on FLYW have underperformed (29% win rate at T+20, avg alpha -4.00%)
Financial Impact
Open-market sales of $3.12M (0.17% of market cap); tax-withholding surrenders of $1.89M (non-cash, no economic signal)
Risk Factors
- COO's large sale could signal internal concerns about near-term performance or guidance
- Cluster occurs ahead of potential Q2 2026 earnings; insider selling before a print is a red flag
- Historical underperformance of bullish calls on FLYW suggests the stock may face continued headwinds
Market Snapshot
Documents Analyzed
This report is based on 1 SEC document filed with EDGAR.
| Document | Accession Number |
|---|---|
| CLUSTER Data (Synthetic) | cluster-FLYW-1780607707247 |
Filters
| Type | Now | ||||
|---|---|---|---|---|---|
|
Jun 4, 2026
2d ago
|
Insider Cluster
| — | awaiting T+1 | — | — |
|
Jun 4, 2026
2d ago
|
Insider Cluster
| — | awaiting T+1 | — | — |
|
Jun 4, 2026
2d ago
|
144
| $14.58 $14.40 | ▼ −1.23% | ▲ +1.36% | $14.40 (−1.23%) |
|
Jun 2, 2026
4d ago
|
144
| $15.14 $14.61 | ▼ −3.50% | ▼ −2.81% | $14.40 (−4.89%) |
|
May 20, 2026
17d ago
|
Press Release
| $15.91 $16.16 | ▲ +1.57% | ▲ +1.38% | $14.40 (−9.49%) |
|
May 15, 2026
22d ago
|
8-K
| $16.06 $16.02 | ▼ −0.25% | ▼ −0.19% | $14.40 (−10.34%) |
|
May 6, 2026
4w ago
|
Insider Cluster
| $17.51 $17.73 | ▲ +1.26% | ▲ +1.59% | $14.40 (−17.76%) |
|
May 6, 2026
4w ago
|
Insider Cluster
| $17.51 $17.73 | ▲ +1.26% | ▲ +1.59% | $14.40 (−17.76%) |
|
May 5, 2026
4w ago
|
8-K
| $17.51 $17.73 | ▲ +1.26% | ▲ +1.59% | $14.40 (−17.76%) |
|
Apr 29, 2026
5w ago
|
Press Release
| $13.68 $13.51 | ▼ −1.24% | ▼ −2.27% | $14.40 (+5.26%) |
US Market Status
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