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.
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
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
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
Investment Themes
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 | ||||
|---|---|---|---|---|---|
Oct 27, 2026 today | SC 13G/A | $19.16 | awaiting T+60 | — | $18.84 (−1.67%) |
Oct 22, 2026 5d ago | Press Release | $19.15 | awaiting T+60 | — | $18.84 (−1.62%) |
Sep 15, 2026 6w ago | Insider Cluster | $17.80 | awaiting T+60 | — | $18.84 (+5.84%) |
Sep 10, 2026 6w ago | Insider Cluster | $17.75 | awaiting T+60 | — | $18.84 (−6.14%) |
Sep 3, 2026 7w ago | Insider Cluster | $18.55 | awaiting T+60 | — | $18.84 (−1.56%) |
Aug 19, 2026 9w ago | Press Release | $18.83 | awaiting T+60 | — | $18.84 (+0.05%) |
Aug 12, 2026 10w ago | Press Release | $17.46 | awaiting T+60 | — | $18.84 (+7.90%) |
Aug 7, 2026 11w ago | 144 | $17.78 | awaiting T+60 | — | $18.84 (+5.96%) |
Jul 6, 2026 16w ago | Insider Cluster | $18.55 $17.50 | ▼ −5.66% | ▼ −7.66% | $18.84 (+1.56%) |
Jun 26, 2026 17w ago | Institutional Cluster | $17.54 $17.13 | ▼ −2.37% | ▼ −6.85% | $18.84 (+7.41%) |
US Market Status
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