What happened
Waystar Holding Corp. (NASDAQ: WAY) CEO and director Matthew J. Hawkins sold 82,500 shares on 2026-10-06. The filing says the shares sold at a weighted average price of $26.23 each, for about $2.16 million. Hawkins also exercised 82,500 vested stock options at $4.14 a share. The shares changed hands in multiple transactions from $25.98 to $26.60. Before the sale, Hawkins held 1,887,294 shares after the option exercise. After the sale, he held 1,804,794 shares.
The Form 4 says the trades were made under a Rule 10b5-1 trading plan adopted on March 13, 2026. The report also lists indirect option blocks of 66,374 shares in a 2024 grantor retained annuity trust and 46,208 shares in a 2025 grantor retained annuity trust.
Key numbers
| Metric | Latest | Change | Source |
|---|---|---|---|
| shares sold | 82,500 shares | SEC Form 4 | |
| sale price | $26.23 a share | SEC Form 4 | |
| total sale value | about $2.16 million | SEC Form 4 | |
| shares held after sale | 1,804,794 shares | SEC Form 4 | |
| option exercise price | $4.14 a share | SEC Form 4 | |
| shares held before sale | 1,887,294 shares | SEC Form 4 |
Why it matters
OptimistFi's case is that Waystar depends on healthcare-payment complexity keeping providers on its independent cloud workflow layer. Hawkins' sale is mixed for that view because the filing ties it to a Rule 10b5-1 plan adopted months earlier. The 82,500 shares were about 4.4% of the 1,887,294 shares Hawkins held before the sale. He still held 1,804,794 shares after the transaction, so the CEO remains a large holder.
The sale price, exercise price and after-sale holding give investors a clear reference point for later filings. Those filings may show whether the stake keeps drifting or stabilizes.
The plan language also matters because it keeps the sale from looking like a fresh discretionary shift. The indirect trust holdings are listed separately from the sale. The filing names them as 66,374 shares in one trust and 46,208 shares in another.
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What's next
The next test is Waystar Holding Corp.'s next quarterly report. If Hawkins keeps a similar holding level, this filing stays a routine insider update. If later filings show more plan-based selling, the case weakens. A steadier stake would leave the investment case closer to unchanged. More selling would weaken it. That report will be the next scheduled check on the insider stake for investors.
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Sources
- SEC Form 4 — Matthew J. Hawkins sold 82,500 shares and held 1,804,794 afterward.
- Calculated from SEC Form 4 — 82,500 shares were about 4.4% of the 1,887,294 shares held before the sale.
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Originally published on OptimistFi, evidence-first equity research. More at optimistfi.com.
