Form 4: Waystar CBO Exercises Options, Sells Shares in Pre-Planned Trade

Waystar Holding Corp.'s Chief Business Officer, Eric L. Sinclair III, exercised stock options and subsequently sold an equal number of common shares totaling 40,225, as part of a pre-arranged 10b5-1 trading plan.

Summary

• Eric L. Sinclair III, Chief Business Officer of Waystar Holding Corp., engaged in a series of transactions on January 20, 2026.
• He exercised stock options to acquire 7,562 shares of common stock at an exercise price of $18.19 per share.
• He also exercised stock options to acquire an additional 32,663 shares of common stock at an exercise price of $4.14 per share.
• Immediately following these exercises, Mr. Sinclair sold 40,225 shares of common stock at a weighted average price of $30.0827 per share, with individual transactions ranging from $30.00 to $30.23.
• These transactions were executed automatically pursuant to a Rule 10b5-1(c) plan adopted on August 24, 2025.
• Following these transactions, Mr. Sinclair beneficially owns 474,826 shares of common stock, which includes unvested Restricted Stock Units (RSUs).
• He retains 173,938 stock options with an exercise price of $18.19 and 6,141 stock options with an exercise price of $4.14.

Sentiment

Score: 6

Explanation: The transactions represent a routine exercise of options and subsequent sale of shares under a pre-arranged 10b5-1 plan, which is a common practice for executives to manage their equity compensation and liquidity. The insider still holds a substantial number of shares and options.

Positives

• The Chief Business Officer exercised options at significantly lower prices ($18.19 and $4.14) compared to the sale price ($30.0827), indicating a profitable transaction for the insider.
• The transactions were conducted under a pre-arranged Rule 10b5-1(c) plan, which suggests the sale was not based on new, non-public information.

Negatives

• The sale of 40,225 shares by a key executive could be perceived as a slight negative signal, although mitigated by the 10b5-1 plan.

Stakeholder Impact

• Shareholders: The sale of shares by a CBO, even under a 10b5-1 plan, might be viewed with slight caution by some investors, though the pre-planned nature mitigates concerns about opportunistic selling. The insider still retains significant equity.

Key Dates

Recommendation

The filing details a pre-planned insider transaction involving the exercise of options and subsequent sale of an equal number of shares. This is a routine event for executives managing their compensation and liquidity, and the 10b5-1 plan mitigates any negative signal from the sale. It does not provide new information about the company's operational performance or strategic direction that would warrant a change in investment recommendation. The insider retains significant equity exposure.

Keywords

Waystar Holding Corp., WAY, SEC Form 4, Insider Trading, Stock Options, Share Sale, Eric L. Sinclair III, Chief Business Officer, 10b5-1 Plan, Equity Compensation