Form 4: Waystar Officer Sells Shares, Tax Withholding Reported

Waystar Holding Corp.'s Chief Transformation Officer, T. Craig Bridge, reported the sale of 85,000 shares under a 10b5-1 plan and the withholding of 14,488 shares for tax obligations.

Summary

• T. Craig Bridge, Chief Transformation Officer of Waystar Holding Corp., reported two non-derivative security transactions.
• On June 6, 2025, 14,488 shares of common stock were disposed of at a price of $40.55 per share. These shares were withheld to cover tax obligations upon the vesting of Non-Qualified Stock Options granted on June 6, 2024.
• This tax-related transaction was not timely filed, and the reported beneficial ownership includes a correction for a prior misclassification of an option exercise, ensuring the ending balance is accurate.
• On September 8, 2025, 85,000 shares of common stock were sold at a weighted average price of $40.0618 per share, with individual transaction prices ranging from $40.00 to $40.22.
• This sale was executed automatically pursuant to a Rule 10b5-1(c) plan adopted by Mr. Bridge on November 27, 2024.
• Following these transactions, Mr. Bridge beneficially owns 583,355 shares of Waystar Holding Corp. common stock, which includes unvested Restricted Stock Units (RSUs).

Sentiment

Score: 5

Explanation: The filing reports routine insider transactions, including tax withholding and a pre-planned sale under a 10b5-1 plan. While an officer sale can be seen as a slight negative, the pre-planned nature mitigates this. The late filing of one transaction is a minor administrative issue.

Positives

• The sale of 85,000 shares was conducted under a pre-arranged Rule 10b5-1(c) plan, indicating a planned disposition rather than an immediate reaction to market conditions.
• The reported beneficial ownership includes a correction to prior filings, ensuring accuracy and transparency of current holdings.

Negatives

• The transaction involving shares withheld for taxes on June 6, 2025, was not timely filed.
• An officer selling a significant number of shares (85,000) could be perceived negatively by some investors, even if under a 10b5-1 plan.

Future Outlook

NA

Management Comments

• The ending balance reported herein is accurate and reflects the Reporting Person's current holdings.
• The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Common Stock sold at each separate price in the range set forth in this footnote.

Industry Context

This filing is specific to an individual insider's transactions and does not provide information relevant to broader industry trends or competitive landscape.

Stakeholder Impact

• Shareholders: The sale of shares by a Chief Transformation Officer, even under a 10b5-1 plan, could be interpreted by some as a slight lack of confidence, though the pre-planned nature reduces this impact. The correction of prior filings ensures transparency and accurate reporting of insider holdings.
• Regulatory Authorities: The late filing of one transaction indicates a minor compliance lapse that the SEC would note.

Next Steps

• The Reporting Person undertakes to provide full information regarding the number of shares of Common Stock sold at each separate price in the range, upon request.

Key Dates

Recommendation

This Form 4 filing details routine insider transactions, including tax-related share withholding and a pre-planned sale under a 10b5-1 plan. While the sale of 85,000 shares by a Chief Transformation Officer is notable, its execution under a pre-established plan minimizes its signaling effect on the company's immediate prospects. The late filing of a tax-related transaction is an administrative oversight rather than a material event. The filing does not provide new fundamental information about Waystar Holding Corp. that would warrant a change in investment thesis, thus a 'hold' recommendation is appropriate.

Keywords

Waystar Holding Corp, WAY, T. Craig Bridge, Chief Transformation Officer, Form 4, insider trading, stock sale, 10b5-1 plan, tax withholding, common stock, beneficial ownership