TL;DR
Two senior officers dispose of shares totaling over $3.5 million as the healthcare technology company approaches quarterly earnings.
July 23, 2025
Waystar Holding Corp (NASDAQ: WAY) experienced significant insider selling activity on July 21, 2025, with two senior executives disposing of shares worth a combined $3.5 million.
The transactions occurred as the $6.4 billion healthcare technology company prepares for its second-quarter earnings report.
Executive Transaction Details
Bridge T. Craig
Chief Transformation Officer Bridge T. Craig executed the larger transaction, selling 85,000 shares at a weighted average price of $37.0922.
The sale generated total proceeds of $3,152,837, with individual transaction prices ranging from $36.36 to $37.42 per share.
Eric L. (Ric) Sinclair III
Chief Business Officer Eric L. (Ric) Sinclair III completed a smaller but substantial sale of 9,702 shares for total proceeds of $359,938.
Sinclair’s shares were sold at prices ranging from $36.41 to $37.42, reflecting similar market pricing to Craig’s transaction.
Rule 10b5-1 Trading Plans
Both executives conducted their sales under pre-established Rule 10b5-1 trading plans, indicating strategic portfolio management rather than reactive decision-making.
Craig adopted his trading plan on November 27, 2024, while Sinclair established his more recent plan on February 19, 2025.
Following these transactions, Craig directly owns 682,843 shares of Waystar common stock, including unvested restricted stock units. Sinclair retains direct ownership of 490,870 shares, also inclusive of unvested equity awards.
Strong Market Performance Context
The insider sales occur against a backdrop of strong stock performance for Waystar.
The company has delivered an impressive 59% return over the past year, significantly outperforming broader market indices.
Currently trading around $36.57, the stock reflects investor confidence in the healthcare technology platform provider.
Analyst sentiment remains positive despite the insider selling activity.
- Canaccord Genuity maintains a Buy rating with a $47 price target ahead of upcoming earnings.
- Mizuho recently initiated coverage with an Outperform rating and $48 target price. Mizuho specifically noted Waystar’s market share gains following a competitor’s cyberattack.
Strategic Developments
Recent corporate developments support the company’s growth trajectory. Waystar has strengthened its board of directors with appointments of Aashima Gupta from Google Cloud and Michael Roman, former CEO of 3M Company.
Credit rating agencies have responded favorably, with both Fitch Ratings and S&P Global Ratings upgrading Waystar’s credit profile citing reduced leverage expectations and stronger market positioning.
The healthcare technology company maintains a “GREAT” financial health score according to InvestingPro analysis, reflecting solid operational fundamentals despite current elevated valuation metrics.