Form 4: Waystar Director Sells $168M in Shares

Paul G. Moskowitz, a director and 10% owner of Waystar Holding Corp., reported the sale of over 4.2 million shares for $168 million and the distribution of over 500,000 shares.

Summary

• Paul G. Moskowitz, a Director and 10% Owner of Waystar Holding Corp. (WAY), reported transactions on September 12, 2025.
• A total of 4,295,139 shares of Common Stock were sold at a price of $39.21 per share, totaling approximately $168.4 million.
• The sale was conducted through a registered public offering by BCPE Derby Investor, LP and BCPE Derby (DE) SPV, LP, entities associated with Bain Capital.
• An additional 516,371 shares of Common Stock were distributed by Derby Investor and Derby SPV Investor to their respective members or partners in connection with charitable gifts.
• Following these transactions, the indirect beneficial ownership of Mr. Moskowitz, through the Bain Capital Entities, stands at 13,243,539 shares.
• The transactions were made pursuant to a Rule 10b5-1(c) plan, indicating a pre-arranged sale schedule.

Sentiment

Score: 4

Explanation: The sentiment is slightly negative due to a significant reduction in insider ownership by a director and 10% owner. While the 10b5-1 plan mitigates the negative signal, the sheer volume of shares sold and distributed represents a notable decrease in insider commitment.

Positives

• The sale was executed pursuant to a Rule 10b5-1(c) plan, suggesting a pre-scheduled transaction not based on immediate, non-public information.
• The sale price of $39.21 per share indicates a specific valuation achieved for a significant block of shares.

Negatives

• A substantial reduction in beneficial ownership by a director and 10% owner, totaling 4,295,139 shares, which could be perceived negatively by the market.
• The distribution of 516,371 shares, while for charitable gifts, also reduces the overall insider stake.

Risks

• Shares distributed in connection with charitable gifts are subject to lock-up agreements restricting their sale until November 11, 2025, except with prior written consent from J.P. Morgan Securities LLC, which could impact market liquidity or price if a large block is released post-lock-up.

Future Outlook

The lock-up agreements on the distributed shares are set to expire on November 11, 2025, which could potentially introduce additional shares into the market at that time.

Industry Context

Insider selling, even when pre-planned via a 10b5-1 plan, is a common event in the market. While a 10b5-1 plan mitigates concerns about opportunistic selling based on undisclosed information, a significant reduction in a director's and 10% owner's stake can still be interpreted by investors as a signal regarding the company's valuation or future prospects.

Related Party Transactions

• The transactions involve entities (BCPE Derby Investor, LP and BCPE Derby (DE) SPV, LP) through which Paul G. Moskowitz, a director, indirectly holds beneficial ownership, indicating related party dealings.

Stakeholder Impact

• Shareholders may view the significant insider selling as a signal regarding the company's valuation or future prospects, potentially influencing investor sentiment and trading decisions.
• The lock-up expiration on distributed shares could lead to increased supply in the market, potentially impacting share price.

Next Steps

• Monitoring the expiration of lock-up agreements on November 11, 2025, for the distributed shares.

Key Dates

Recommendation

The recommendation is 'hold' because while the significant insider selling by a director and 10% owner is a notable event, the transaction was executed under a Rule 10b5-1 plan, which suggests it was pre-scheduled and not based on new, negative information. This mitigates the immediate negative implications. However, the substantial reduction in insider stake warrants caution, preventing a 'buy' recommendation. Investors should monitor future developments and the impact of the lock-up expiration.

Keywords

Waystar, WAY, Insider Trading, Stock Sale, Paul Moskowitz, Bain Capital, Form 4, Beneficial Ownership, Rule 10b5-1