Form 4: Waystar CFO Sells Shares Under 10b5-1 Plan

Waystar Holding Corp.'s CFO, Steven M. Oreskovich, executed a pre-planned sale of 16,666 common shares following the exercise of stock options.

Summary

• Chief Financial Officer Steven M. Oreskovich engaged in multiple transactions involving Waystar Holding Corp. common stock.
• On June 6, 2025, 14,038 shares were withheld for tax purposes upon the vesting of Non-Qualified Stock Options, valued at $40.55 per share. This transaction was not timely filed.
• On September 10, 2025, Oreskovich acquired 16,666 shares by exercising stock options at an exercise price of $4.14 per share.
• Concurrently on September 10, 2025, 16,666 shares were sold at a weighted average price of $40.4925, with individual transactions ranging from $40.09 to $40.90.
• Both September 10, 2025, transactions were executed automatically under a Rule 10b5-1 plan adopted on September 6, 2024.
• Following these transactions, Oreskovich beneficially owns 354,512 shares of common stock, which includes unvested Restricted Stock Units (RSUs).
• He also holds 101,205 vested stock options with an expiration date of September 17, 2028.

Sentiment

Score: 6

Explanation: The filing reports routine insider transactions, including an option exercise and sale under a 10b5-1 plan, which is neutral. The only minor negative is the untimely filing of a tax-related transaction, but this is a compliance issue rather than a fundamental business concern.

Positives

• The transactions on September 10, 2025, were executed under a pre-arranged Rule 10b5-1 plan, indicating a pre-scheduled disposition rather than a reaction to immediate market conditions.
• The exercise price of the options ($4.14) is significantly lower than the sale price ($40.4925), indicating a substantial gain for the CFO on the exercised shares.

Negatives

• The transaction on June 6, 2025, involving shares withheld for tax, was not timely filed, which represents a compliance oversight.

Risks

• Compliance risk due to the untimely filing of the June 6, 2025, transaction, which could draw regulatory scrutiny.

Future Outlook

The filing does not provide explicit forward-looking statements or guidance beyond the scheduled transaction dates and option expiration.

Industry Context

This Form 4 filing details routine insider transactions (option exercise and sale) by a Chief Financial Officer, which are common in the healthcare technology and software industry as executives manage their equity compensation and diversify their personal portfolios. Such transactions are generally not indicative of broader industry trends unless they are unusually large or frequent across multiple executives.

Comparison to Industry Standards

• The transactions are standard for executive compensation and personal financial planning within the industry.
• The use of a Rule 10b5-1 plan is a common practice among executives to mitigate accusations of insider trading by pre-scheduling transactions.
• The exercise of options and subsequent sale of shares is a typical method for executives to realize value from their equity compensation.
• The price range for the sale ($40.09 to $40.90) is consistent with market trading activity for a company of Waystar's profile.

Stakeholder Impact

• Shareholders: The sale by a CFO could be viewed as a minor negative, but the pre-planned nature under a 10b5-1 plan mitigates concerns. The realization of significant gains by the CFO from options exercise demonstrates the value of equity compensation.
• Regulatory Authorities: The untimely filing of the June 6, 2025, transaction may draw attention from the SEC regarding compliance with Section 16(a) reporting requirements.

Next Steps

• The Reporting Person undertakes to provide full information regarding the number of shares sold at each separate price in the reported range upon request to the Issuer, any security holder, or the SEC staff.

Key Dates

Recommendation

This Form 4 filing details routine insider transactions by the CFO, including an option exercise and a pre-planned sale under a 10b5-1 plan. While there was a minor compliance issue with an untimely filing for a tax-related transaction, these events do not provide new fundamental information about Waystar Holding Corp.'s operational performance, strategic direction, or financial health that would warrant a change in investment thesis. The transactions are typical for executive compensation management and do not signal a significant positive or negative shift in the company's outlook. Therefore, a 'hold' recommendation is appropriate as the filing does not present a compelling reason to alter existing positions.

Keywords

Waystar Holding Corp., WAY, Steven M. Oreskovich, CFO, Form 4, Insider Trading, Stock Options, Share Sale, Rule 10b5-1, Equity Compensation