Waystar Holding Corp. SEC Filings

Waystar Holding Corp. insider transactions by CFO Steven M. Oreskovich. On 06/06/2025 14,038 shares were withheld to satisfy taxes upon vesting of non‑qualified stock options, reported at a price of $40.55, leaving 354,512 shares beneficially owned. On 09/10/2025 the reporting person acquired 16,666 shares by exercising options at a $4.14 exercise price under a plan intended to satisfy Rule 10b5‑1, and on the same date sold 16,666 shares in multiple transactions at a weighted average price of $40.4925, returning beneficial ownership to 354,512 shares. The reporting person holds 101,205 stock options following these events. The filing discloses that the June 6, 2025 tax‑withholding transaction was not timely filed.

Waystar Holding Corp. (WAY) insider sale notice: This Form 144 reports a proposed sale of 25,869 common shares through Morgan Stanley Smith Barney on 09/10/2025, with an aggregate market value of $1,057,783.41 and listing on NASDAQ. The shares were acquired the same day via exercise of stock options and payment was in cash. The filer also recorded two prior 10b5-1 sales this year: 8,623 shares on 08/11/2025 for $297,391.75 and 8,623 shares on 07/10/2025 for $324,461.93. The notice includes the standard representation that the seller is not aware of undisclosed material adverse information.

Waystar Holding Corp. (WAY) Form 144 discloses a proposed sale of 16,666 common shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $681,472.74. The shares represent part of the issuer's outstanding common stock of 174,238,972 shares and are planned for sale on or about 09/10/2025 on NASDAQ. The filing states these shares were acquired on 09/10/2025 by exercise of stock options and paid for in cash the same day.

The filing also reports prior 10b5-1 sales by STEVEN M ORESKOVICH of 16,396 shares on 06/11/2025 for gross proceeds of $667,489.36. Standard Rule 144 representations about absence of undisclosed material information are included.

Waystar insider transactions by Chief Transformation Officer Bridge T. Craig show two reported changes in beneficial ownership. On 06/06/2025, 14,488 shares were disposed at $40.55 per share through withholding to satisfy taxes on vested non-qualified stock options granted 06/06/2024; the filing states this transaction was not timely filed and that the post-transaction balance includes a correction for a prior misclassified option exercise, leaving 668,355 shares beneficially owned. On 09/08/2025, 85,000 shares were sold at a weighted average price of $40.0618 (range $40.00–$40.22) under a 10b5-1 plan adopted 11/27/2024, leaving 583,355 shares. The form is signed by an attorney-in-fact on 09/10/2025.

Waystar Holding Corp. insider filing by Eric L. Sinclair III reports a tax-withholding share disposition and automatic transactions under a 10b5-1 plan plus option activity. On 06/06/2025 the reporting person had 16,044 shares withheld to pay taxes on option vesting at a price of $40.55, leaving 474,826 shares beneficially owned (this total includes unvested RSUs). On 09/08/2025 the reporting person acquired 19,404 shares via exercise/plan at $4.14 and concurrently sold 19,404 shares at a weighted average price of $40.0285 (sales occurred across $40.00–$40.25). The acquisition on 09/08/2025 was automatic under a plan adopted 02/19/2025 intended to satisfy Rule 10b5-1(c). The filing corrects prior reporting to reflect an earlier misclassification of an option exercise and states the option lot is vested and exercisable.

Kimberly S. Wittman, Chief People Officer of Waystar Holding Corp. (WAY), reported transactions affecting her holdings. On 06/06/2025 she had 2,670 shares of common stock withheld to cover taxes related to vesting of non-qualified stock options granted on 06/06/2024; the withheld shares were valued at $40.55 each. After correcting a prior misclassification, her post-transaction direct beneficial ownership was reported as 193,261 shares. On 09/04/2025 she acquired 18,000 shares and was granted 18,000 stock options with a $21.50 exercise price that vest beginning 06/06/2025 and expire 06/06/2034.

The filing discloses a correction to earlier filings and notes the 06/06/2025 tax-withholding transaction was not timely filed. The form was executed by an attorney-in-fact on 09/08/2025.

Waystar Holding Corp. (WAY) insider Craig Bridge notified the SEC of a proposed sale under Rule 144 of 85,000 common shares through Morgan Stanley Smith Barney, with an aggregate market value of $3,167,950.00. The filing shows those shares were acquired on 07/19/2024 via previously exercised stock options and paid in cash on the same date. The notice lists an approximate sale date of 09/08/2025 and reports 174,238,972 shares outstanding for the issuer, with the broker exchange listed as NASDAQ. The filing also discloses prior 10b5-1 sales by Craig Bridge during the past three months: 85,000 shares on 07/21/2025 for gross proceeds of $3,152,837.00 and 15,946 shares on 06/11/2025 for $649,177.61. The filer certifies compliance with Rule 10b5-1 representations in the signature section.

Waystar Holding Corp. (WAY) Form 144 notice reports a proposed sale of 48,507 common shares through Morgan Stanley Smith Barney LLC on 09/08/2025 with an indicated aggregate market value of $1,807,855.89. The shares were acquired on 09/08/2025 by exercise of stock options and payment was in cash. The filing lists four prior 10b5-1 sales by the same account during 06/20/2025–08/20/2025, each for 9,702 shares. The filing supplies broker, acquisition method, number of shares outstanding (174,238,972) and confirms the seller represents no undisclosed material information.

Waystar Holding Corp. (WAY) insider activity by Chief Marketing Officer Melissa F. Miller. The report shows three equity transactions: 2,623 shares were withheld to pay taxes upon vesting of previously granted non-qualified stock options on 06/06/2025, reducing holdings to 193,261 shares. On 08/26/2025 a 10b5-1 plan executed the acquisition of 3,400 shares at $18.19 and simultaneous sales of 3,400 shares at a weighted-average price of $37.0095, leaving beneficial ownership at 193,261 (after a corrected prior misclassification). The Form notes the option grant dates, vesting schedule, and that the 10b5-1 plan was adopted on 11/20/2024.