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, 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. At 18.1% revenue growth, the CEO's choice to cash out rather than hold is difficult 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 signal a long-term value view; 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 — compressed for a software business with 69.1% gross margins and $314 million in free cash flow. The bull case must still account for $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; it holds if Waystar prints another EPS beat, extending a run of three 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 →.
Basis Report is independent research for informational purposes. It is not investment advice and not a recommendation to buy or sell any security.
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.