Waystar CEO Sells at $25 While Analysts Target $33
Waystar Holding Corp. CEO Matthew Hawkins has sold more than $3.6 million of WAY stock through open-market trades since mid-July, all while the analyst consensus price target sits 36% above the curren
Waystar CEO Sells at $25 While Analysts Target $33
NEW YORK, August 19 —
Waystar Holding Corp. (WAY) CEO Matthew Hawkins has converted $3.68 million of company stock to cash through four open-market sales since mid-July, at prices both Wall Street's consensus and his own board's grant machinery treat as materially discounted. The question the trade pattern raises is whether he is diversifying rationally or reading a ceiling the public models have not.
- Q2 2026: EPS $0.43 vs. estimate, a 7.6% beat, marking the third beat in four quarters. (8-K, July 29)
- Trailing revenue $1.21 billion, up 18.1% YoY; gross margin 69.1%; free cash flow $314 million.
- Analyst consensus price target $33.17, 36% above the current $24.32; CEO sold $3.68 million of stock in 30 days.
The Exercise-and-Sell Pattern
Hawkins executed a textbook exercise-and-sell program, converting 153,500 options struck at $4.14 into open-market sales at $23.02 to $25.04 across four transactions between July 15 and August 13. Each sale was same-day paired with an option exercise, capturing the full intrinsic spread in cash rather than holding the resulting equity. The program generated $3.68 million in gross proceeds with zero offsetting open-market purchases over the 90-day window. Waystar provides cloud-based software for hospital and payer billing across the full revenue cycle, from financial clearance to denials prevention. Revenue has grown 18.1%, which makes the CEO's choice to cash out, rather than hold, harder to explain away.
The Grant-and-Sell Contradiction
The compensation committee's timing makes the CEO's exit price harder to dismiss. On August 1, while Hawkins was actively selling, the board granted him 908,265 new equity awards, the largest single grant in the filing window, alongside 90,827 shares to Chief Commercial Officer Todd Woods, 232,061 to Chief Legal Officer Gregory Packer, and 205,470 to Chief Transformation Officer Craig Bridge. Compensation grants embed an implicit view on long-term value; a board that hands the CEO 900,000-plus shares treats current levels as worth accumulating. That makes Hawkins' concurrent cash-out at $25 structurally inconsistent, unless the comp committee and CEO are solving for different horizons.
| Ticker | Mkt cap | Fwd P/E | 52-wk |
|---|---|---|---|
| WAY | $4.7B | 13.2x | -30.7% |
| BTSG | $11.8B | 26.1x | +151.8% |
| ULS | $15.4B | 29.3x | +13.5% |
| LIF | $3.6B | 24.9x | -45.1% |
| PACS | $7.0B | 16.3x | +267.4% |
| LOAR | $7.3B | 47.9x | +5.9% |
A $33 Target Priced on What, Exactly
The analyst consensus of $33.17, 36% above current levels, implies a forward PE of 13.0x, which looks compressed for a software business with 69.1% gross margins and $314 million in free cash flow. The constraint the bull case must explain is $1.29 billion in net debt against a $4.66 billion market cap, a leverage ratio that amplifies any guidance cut. The thesis breaks if Q3 revenue growth decelerates from the current pace; it holds if Waystar prints a Q3 EPS beat, extending a record of three beats in four quarters. Run the DCF calculator to stress-test those assumptions, or pull the full picture at the free Waystar Holding Corp. deep-dive →.
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Waystar Holding Corp. CEO Matthew Hawkins has sold more than $3.6 million of WAY stock through open-market trades since mid-July, all while the analyst consensus price target sits 36% above the current share price and the board just handed him over 900,000 new equity awards. The CEO is cashing out at $23–$25 in a stock his own company's analysts believe is worth $33.