Every Form 4 that Waystar Holding Corp. (WAY) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow WAY and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full WAY filings page.
Waystar Holding Corp. (symbol: WAY) is the issuer of record for a Form 4 filing submitted to the SEC. Khanna Amit reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. (WAY) reported that Chief Product & Technology Officer Amit Khanna received an equity award on August 17, 2026. He was granted 390,625 restricted stock units (RSUs), each representing one share of common stock. Subject to continued service, 6.25% of the RSUs vest quarterly during the first 12 months after the grant date, and 25% vest on each August 17 thereafter through August 17, 2030. Following this grant, Khanna is reported as directly holding 390,625 shares/RSUs, including unvested RSUs. No Rule 10b5-1 trading plan is indicated.
Waystar Holding Corp. (WAY) reports that Chief Legal Officer Gregory R. Packer had 6,754 shares of common stock withheld on September 1, 2026 to pay tax liabilities arising from the vesting of previously granted restricted stock units (RSUs). The shares were valued at $25.73 per share for this tax-withholding transaction, and Packer now directly holds 418,255 shares, which include unvested RSUs.
The RSUs were granted on August 18, 2025, and their vesting schedule was modified by the Talent & Compensation Committee to provide for 25% vesting on September 1, 2026 and 25% vesting on each of the next three anniversaries of the Vesting Commencement Date. No Rule 10b5-1 trading plan is reported for this tax-withholding disposition.
Waystar Holding Corp. (WAY) reported that Chief Transformation Officer Bridge T. Craig had 30,792 shares of common stock withheld on September 1, 2026 to pay tax liabilities arising from the vesting of restricted stock units granted on April 1, 2025. The withholding price was $25.73 per share. After this tax-withholding disposition, Craig held 833,234 shares of common stock directly, which the company notes includes unvested RSUs. No Rule 10b5-1 trading plan is reported for this transaction.
Waystar Holding Corp. (WAY) reported that Chief Executive Officer and director Matthew J. Hawkins exercised stock options for 82,500 shares of common stock at an exercise price of $4.14 per share on September 2, 2026, then sold 82,500 shares at a weighted average price of $25.9707 per share. The exercise and sale were effected automatically under a trading plan adopted on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). On September 1, 2026, 30,287 shares were withheld at $25.73 per share to pay taxes upon vesting of restricted stock units, and the filing notes a modified RSU vesting schedule. Hawkins continues to hold vested stock options on common stock, including positions held directly and through 2024 and 2025 grantor retained annuity trusts, with these trust-related shifts characterized as changes in the form of beneficial ownership without a change in pecuniary interest under Rule 16a-13.
Wegner Alpana reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. granted its Chief Financial Officer, Alpana Wegner, 162,112 restricted stock units (RSUs) of common stock on July 24, 2026. Subject to continued service, 6.25% of the RSUs vest quarterly during the first 12 months after grant, and 25% vest on each July 22 through July 22, 2030. Each RSU represents a contingent right to receive one share of common stock upon settlement. Following this award, Wegner directly holds 162,112 shares/RSUs, including unvested RSUs.
Waystar Holding Corp. Chief Executive Officer Matthew J. Hawkins reported option exercises and related share sales. He exercised stock options for 82,500 shares of common stock at an exercise price of $4.14 per share and sold the same number of shares in open-market transactions at weighted average prices of $25.0358 and $25.0121 per share. These trades were executed pursuant to a Rule 10b5-1(c) trading plan adopted on March 13, 2026. Hawkins continues to hold vested options indirectly through 2024 and 2025 grantor retained annuity trusts covering 343,135 and 46,208 underlying shares, respectively.
Woods Todd Charles reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. reported that Chief Commercial Officer Todd Charles Woods received a grant of 90,827 restricted stock units (RSUs) of Common Stock on 2026-08-01. The RSUs vest over 2 years, with 12.5% vesting each quarter in year 1 and 50% vesting in year 2. Following this grant, Woods holds 220,506 shares and RSUs directly, including unvested RSUs.
Waystar Holding Corp. reported equity compensation changes for Chief Legal Officer Gregory R. Packer. On August 1, 2026, he received a grant of 232,061 restricted stock units (RSUs), vesting over two years, with 12.5% vesting each quarter in year one and 50% vesting in year two. On April 6, 2026, 4,016 shares of common stock were withheld at $23.69 per share to pay taxes upon vesting of RSUs granted on April 1, 2025; the number of shares withheld was based on the sale price of shares sold on April 7, 2026 in a sell-to-cover transaction.
Hawkins Matthew J. reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. reported that Chief Executive Officer Matthew J. Hawkins received a grant of 908,265 restricted stock units, each representing one share of common stock. The RSUs vest in three equal annual installments from the grant date, and his directly held common-stock position after the grant is 1,835,081 shares, including unvested RSUs.
Bridge T. Craig reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. granted Chief Transformation Officer Bridge T. Craig 205,470 restricted stock units (RSUs), each representing one share of common stock. The RSUs vest over 2 years, with 12.5% vesting each quarter in year 1 and 50% vesting in year 2. After this grant, Craig directly holds 864,026 shares of common stock, including unvested RSUs.
Waystar Holding Corp. Chief Executive Officer Matthew J. Hawkins reported exercising stock options for 70,000 shares of common stock at $4.1400 per share and selling 70,000 shares in open-market transactions at weighted average prices of $23.0228 and $23.0873 in mid-July 2026.
The transactions occurred automatically under a Rule 10b5-1 trading plan adopted on March 13, 2026. Hawkins continues to hold common stock and vested stock options, including positions covering 1,468,337 underlying shares directly and 343,135 and 46,208 underlying shares through grantor retained annuity trusts.
Waystar Holding Corp. CEO Matthew J. Hawkins reported a routine tax-related share withholding. On the vesting of Non-Qualified Stock Options granted on June 6, 2024, 47,754 shares of common stock were withheld at $19.23 per share to cover tax obligations.
The Form 4 classifies this as a tax-withholding disposition, not an open-market trade. After this transaction, Hawkins directly holds 926,816 shares of Waystar common stock, which the disclosure notes includes unvested RSUs.
Waystar Holding Corp. Chief People Officer Kimberly S. Wittman reported a routine tax-related share disposition. On the vesting of Non-Qualified Stock Options granted on June 6, 2024, 2,731 shares of common stock were withheld to cover taxes, based on the actual sale price of shares sold on June 9, 2026 pursuant to a sell-to-cover transaction.
After this withholding, Wittman directly holds 270,233 shares of common stock, which the disclosure notes includes unvested RSUs. The transaction is classified as a tax-withholding disposition rather than an open-market sale.
Waystar Holding Corp. Chief Transformation Officer Bridge T. Craig had 12,212 common shares withheld to cover taxes related to the vesting of Non-Qualified Stock Options granted on June 6, 2024. The withholding price was $19.23 per share, and Craig now holds 658,556 shares directly, including unvested RSUs.
Waystar Holding Corp. Chief Financial Officer Steven M. Oreskovich reported a routine tax-related share disposition. On the transaction date, 12,583 shares of common stock were withheld to cover taxes upon vesting of Non-Qualified Stock Options originally granted on June 6, 2024. The withheld shares were valued at $19.23 per share. After this tax-withholding disposition, Oreskovich directly owned 424,200 shares of Waystar common stock, a figure that the filing notes includes unvested RSUs.
Waystar Holding Corp.'s Chief Marketing Officer Melissa F. (Missy) Miller reported a tax-related share disposition. On the transaction date, 2,887 shares of common stock were withheld at $19.23 per share to cover taxes upon vesting of Non-Qualified Stock Options. After this withholding, she held 252,077 shares directly, which the footnote states includes unvested RSUs. This event reflects routine tax withholding rather than an open-market sale.
Waystar Holding Corp. Chief Technology Officer Christopher L. Schremser had 14,751 shares of common stock withheld to cover taxes tied to equity compensation. The shares were valued at $19.23 each and relate to Non-Qualified Stock Options granted on June 6, 2024. After this tax-withholding disposition, he directly holds 495,033 shares of Waystar common stock, which the disclosure notes includes unvested restricted stock units.
DeMichiei Robert reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. director Robert DeMichiei received an equity grant in the form of restricted stock units. The award covers 9,303 RSUs, each representing one share of common stock upon settlement, and was granted at no cash cost per share.
The RSUs vest on the earlier of June 1, 2027 or the first regularly scheduled annual stockholder meeting following the grant date. After this grant, DeMichiei directly holds 46,199 shares of common stock, a figure that includes unvested RSUs.
Gupta Aashima reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. director Aashima Gupta reported receiving a grant of 9,303 shares of Common Stock in the form of restricted stock units. These RSUs vest on the earlier of June 1, 2027 or the first regularly scheduled annual stockholder meeting after the grant. Following this award, Gupta is shown holding 14,437 shares of Common Stock, including unvested RSUs. This is a compensation-related equity grant rather than an open-market purchase or sale.
Roman Michael F reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. director Michael F. Roman reported receiving a grant of 9,303 restricted stock units (RSUs), each representing one share of common stock upon settlement. These RSUs vest on the earlier of June 1, 2027 or the first regularly scheduled annual stockholder meeting after the grant, bringing his direct holdings, including unvested RSUs, to 14,437 shares.
Riefberg Vivian E. reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. director Vivian E. Riefberg received an equity grant in the form of restricted stock units. The filing reports an award of 9,303 shares of Common Stock at a stated price of $0.00 per share, described in the footnotes as RSUs.
The RSUs vest on the earlier of June 1, 2027 or the first regularly scheduled annual stockholder meeting following the grant date, and each unit will settle into one share of Common Stock. After this award, Riefberg holds 23,132 shares, including unvested RSUs.
MILLER HEIDI reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. director Heidi Miller received a grant of 9,303 shares of Common Stock in the form of restricted stock units at a price of $0.00 per share. These RSUs vest on the earlier of June 1, 2027 or the first regularly scheduled annual stockholder meeting following the grant date. After this award, Miller holds 40,917 shares of Common Stock directly, including unvested RSUs, giving her a larger equity stake aligned with the company’s long-term performance.
Waystar Holding Corp. reported that director Priscilla Hung received a grant of 9,303 restricted stock units (RSUs) of common stock at no cash cost. These RSUs vest on the earlier of June 1, 2027 or the first regularly scheduled annual stockholder meeting following the grant date. Each RSU converts into one share of common stock upon settlement. After this award, Hung directly holds 23,132 shares of common stock, including unvested RSUs.
Waystar Holding Corp. director and chairperson John Patrick Driscoll received an equity award of 9,303 shares of Common Stock in the form of restricted stock units. These RSUs vest on the earlier of June 1, 2027 or the first regularly scheduled annual stockholder meeting after the grant date.
Each RSU converts into one share of Common Stock upon settlement. After this award, Driscoll directly holds 100,060 shares of Common Stock, including unvested RSUs. The transaction reflects a compensation-related grant rather than an open-market purchase or sale.
Waystar Holding Corp. reported that Chief Marketing Officer Melissa F. (Missy) Miller acquired 61,703 shares of common stock through a grant of restricted stock units. These RSUs vest in four equal annual installments from the initial grant date through March 1, 2030, with each RSU representing one share upon settlement. Following this equity award, she holds 254,964 shares of common stock directly, including unvested RSUs.
Wittman Kimberly S. reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. reported that Chief People Officer Kimberly S. Wittman received an equity grant in the form of restricted stock units. She was awarded 61,703 shares of Common Stock at no cost as a grant, increasing her direct holdings to 272,964 shares, including unvested RSUs. The RSU award vests in four equal annual installments through March 1, 2030, with each unit representing the right to receive one share of common stock upon settlement. This is a compensation-related grant rather than an open-market stock purchase.
PACKER GREGORY R reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp.’s Chief Legal Officer Gregory R. Packer received a grant of 65,817 restricted stock units (RSUs) of common stock as equity compensation. The RSUs vest in four equal annual installments from the initial grant date through March 1, 2030.
Each RSU represents a contingent right to receive one share of common stock upon settlement. Following this award, Packer directly holds 196,964 shares and RSUs of Waystar common stock, including unvested RSUs, aligning more of his compensation with the company’s long-term performance.
Waystar Holding Corp. reported that Chief Product & AI Officer William Chan received a grant of 82,271 shares of Common Stock as a stock award, at no cash cost to him. The award is in the form of restricted stock units that vest in four equal annual installments through March 1, 2030, with each unit settling into one share of common stock upon vesting.
Following this grant, Chan holds 1,580,812 shares of Common Stock in total, including unvested restricted stock units. His position also includes RSUs issued on October 2, 2025 in connection with Waystar’s acquisition of Iodine Software Holdings, which are subject to a six‑month lock‑up period after the acquisition closing.
Bridge T. Craig reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. disclosed that Chief Transformation Officer Bridge T. Craig received an equity grant of 87,413 shares of Common Stock as restricted stock units at a stated price of $0.00 per share. The RSUs vest in four equal annual installments from the initial grant date through March 1, 2030, with each unit representing a contingent right to one share of common stock upon settlement. Following this grant, Craig holds 670,768 shares of common stock, including unvested RSUs, as direct ownership. This reflects routine stock-based compensation rather than an open‑market purchase.
Schremser Christopher L. reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. reported that Chief Technology Officer Christopher L. Schremser received a grant of 87,413 restricted stock units of Common Stock. The RSUs vest in four equal annual installments from the grant date through March 1, 2030, with each unit delivering one share upon settlement. Following this equity award, Schremser beneficially owns 509,784 shares of Common Stock, including unvested RSUs, all held directly as part of his compensation rather than an open-market purchase.
Oreskovich Steven M reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. Chief Financial Officer Steven M. Oreskovich received a grant of 82,271 shares of common stock in the form of restricted stock units (RSUs). These RSUs vest in four equal annual installments through March 1, 2030, with each RSU delivering one share of common stock upon settlement. After this grant, Oreskovich directly holds 436,783 shares of common stock, including unvested RSUs, reflecting a compensation-related equity award rather than an open-market purchase.
Hawkins Matthew J. reported acquisition or exercise transactions in this Form 4 filing.
Waystar Holding Corp. reported that Chief Executive Officer Matthew J. Hawkins received a grant of 257,096 restricted stock units (RSUs) of common stock. These RSUs vest in four equal annual installments from the grant date through March 1, 2030, encouraging long-term retention. Each RSU represents a contingent right to receive one share of common stock upon settlement. After this award, Hawkins beneficially owns 974,570 shares of common stock, including unvested RSUs, reflecting a significant equity-based compensation stake.
Waystar Holding Corp. director Heidi Miller reported an open-market purchase of 7,200 shares of Common Stock at a weighted average price of $26.248 per share. The purchase was made indirectly through family trusts, and her indirect ownership after the transaction is 7,200 shares.
Separately, Miller reported direct ownership of 31,614 shares of Common Stock, which includes unvested restricted stock units. This filing highlights both her new indirect investment via family trusts and her existing direct equity position in Waystar.
Waystar Holding Corp.'s Chief Business Officer, Eric L. (Ric) Sinclair III, reported multiple transactions in company stock on January 20, 2026. He exercised stock options covering 7,562 shares at $18.19 and 32,663 shares at $4.14, receiving the same number of common shares. He then sold 40,225 shares of common stock at a weighted average price of $30.0827, with individual sale prices ranging from $30.00 to $30.23. Following these trades, he held 474,826 shares of common stock, which includes unvested restricted stock units. After the option exercises, he also held 173,938 and 6,141 stock options in separate grants. The filing notes that these transactions occurred automatically under a Rule 10b5-1(c) trading plan adopted on August 24, 2025.
Waystar Holding Corp. (WAY) filed a Form 4 showing its Chief Marketing Officer exercising stock options and selling the resulting shares. On 11/25/2025, the officer exercised 3,400 stock options at an exercise price of $18.19 per share, acquiring the same number of common shares. On the same day, those 3,400 common shares were sold at a price of $37 per share. After these transactions, the officer beneficially owned 193,261 shares of common stock, which includes unvested restricted stock units. The remaining stock option position was 28,750 options following the reported activity. These trades occurred automatically under a Rule 10b5-1(c) trading plan adopted on November 20, 2024.
Waystar Holding Corp. insider transaction: the company’s Chief Business Officer reported an option exercise and share sale. On 11/20/2025, the officer exercised stock options to acquire 9,701 shares of common stock at $4.14 per share and then sold 9,701 shares of common stock at a weighted average price of $35.2728 per share in multiple trades between $34.79 and $35.80. After these transactions, the officer beneficially owned 474,826 shares of common stock and 48,505 stock options. The filing notes that these trades occurred automatically under a Rule 10b5-1(c) trading plan adopted on February 19, 2025, and that the options exercised are fully vested and expire on 11/01/2027.
Waystar Holding Corp. (WAY) reported an insider transaction by its Chief Technology Officer. On 11/10/2025, the executive exercised 8,623 stock options at $4.14 and sold 8,623 common shares at a weighted average price of $36.1161 under a Rule 10b5-1(c) trading plan adopted on December 6, 2024.
Following the transactions, the executive beneficially owned 422,371 common shares, which include unvested RSUs, and held 77,617 stock options. The reported sales occurred in multiple trades ranging from $35.63 to $36.50. The exercised options are currently vested, with an expiration date of 11/01/2027.
Waystar Holding Corp. (WAY) Chief Business Officer filed a Form 4 for transactions on 10/20/2025 made under a Rule 10b5-1(c) trading plan adopted on February 19, 2025. The officer exercised 9,701 stock options at $4.14 per share and sold 9,701 common shares at a $36.9378 weighted average price, with individual sales ranging from $36.52 to $37.86. Following these transactions, the officer directly beneficially owns 474,826 common shares. The filing notes that the reported holdings include unvested RSUs and the options exercised were vested.
Waystar Holding Corp. (WAY) reported an insider transaction by its Chief Technology Officer. On 10/10/2025, the officer exercised stock options for 8,623 shares at $4.14 per share and sold 8,623 shares at a weighted average price of $36.2072. The sales occurred in multiple trades ranging from $35.66 to $37.22.
Following these transactions, the officer beneficially owned 422,371 shares directly, which includes unvested RSUs. The officer also held 86,240 stock options after the transactions. The activity occurred automatically under a Rule 10b5-1(c) trading plan adopted on December 6, 2024.
Matthew J. Hawkins, Chief Executive Officer and Director of Waystar Holding Corp. (WAY), reported multiple insider transactions. On 06/06/2025 he had 46,657 shares disposed at an average price of $40.55, resulting in reported beneficial ownership of 717,474 shares (which includes unvested RSUs). Subsequent automatic transactions under a plan intended to satisfy Rule 10b5-1 conditions show acquisitions of 12,200 and 12,800 shares on 09/22/2025 and 09/23/2025 at a $4.14 option price (with related sales at weighted average prices of about $38.08). The filing discloses holdings of exercisable stock options with a $4.14 exercise price and additional equity held indirectly through two grantor retained annuity trusts totaling 593,135 options reported indirectly.
Waystar Holding Corp. insider transactions by Chief Business Officer Eric L. Sinclair III. The reporting person acquired 9,701 shares by exercising options at an exercise price of $4.14 and immediately acquired an equal number of underlying shares. The report also shows sale of 9,701 shares of common stock at a weighted-average price of $37.6343, executed across multiple transactions in a price range of $37.24 to $38.14. Following these transactions the reporting person beneficially owned 484,527 shares before the sale and 474,826 shares after. Some holdings include unvested RSUs and the option grants are currently vested. The acquisitions occurred pursuant to an internal plan intended to satisfy Rule 10b5-1(c) conditions.