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Waystar Executive Nets 800% Profit on Stock Options Trade

Filing Impact
(Moderate)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Eric L. Sinclair III (Ric), Chief Business Officer of Waystar Holding Corp (WAY), executed planned transactions under Rule 10b5-1(c) on June 20, 2025:

  • Exercised 9,702 stock options at $4.14 per share
  • Immediately sold 9,702 shares at weighted average price of $37.7877 (range: $37.65-$38.09)
  • Post-transaction holdings: 490,870 shares (direct ownership, including unvested RSUs) and 126,118 stock options

These transactions were executed automatically according to a trading plan established on February 19, 2025. The significant spread between exercise price ($4.14) and sale price ($37.7877) resulted in substantial gains. The executive maintains a considerable equity position in the company following the transaction.

Positive

  • None.

Negative

  • None.
Insider Sinclair III Eric L. (Ric)
Role Chief Business Officer
Sold 9,702 shs ($367K)
Type Security Shares Price Value
Exercise Stock Options (right to buy) 9,702 $0.00 --
Exercise Common Stock 9,702 $4.14 $40K
Sale Common Stock 9,702 $37.7877 $367K
Holdings After Transaction: Stock Options (right to buy) — 126,118 shares (Direct); Common Stock — 500,572 shares (Direct)
Footnotes (1)
  1. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on February 19, 2025 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). Includes unvested RSUs. The price reported in Column 4 is a weighted average price. These shares of common stock, par value $0.01 per share ("Common Stock") of Waystar Holding Corp. (the "Issuer") were sold in multiple transactions ranging from $37.65 to $38.09, inclusive. 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. These options are currently vested.
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4 UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number: 3235-0287
Estimated average burden
hours per response: 0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
X
 Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Sinclair III Eric L. (Ric)
(Last) (First) (Middle)
1550 DIGITAL DRIVE, #300
(Street)
LEHI UT 84043
(City) (State) (Zip)
2. Issuer Name and Ticker or Trading Symbol
Waystar Holding Corp. [ WAY ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director 10% Owner
X Officer (give title below) Other (specify below)
Chief Business Officer
3. Date of Earliest Transaction (Month/Day/Year)
06/20/2025
4. If Amendment, Date of Original Filed (Month/Day/Year)
 6. Individual or Joint/Group Filing (Check Applicable Line)
X Form filed by One Reporting Person
Form filed by More than One Reporting Person
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock 06/20/2025 M 9,702 A $4.14 500,572(1)(2) D
Common Stock 06/20/2025 S 9,702 D $37.7877(3) 490,870(1)(2) D
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year) 7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Stock Options (right to buy) $4.14 06/20/2025 M 9,702 (4) 11/01/2027 Common Stock 9,702 $0 126,118 D
Explanation of Responses:
1. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on February 19, 2025 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).
2. Includes unvested RSUs.
3. The price reported in Column 4 is a weighted average price. These shares of common stock, par value $0.01 per share ("Common Stock") of Waystar Holding Corp. (the "Issuer") were sold in multiple transactions ranging from $37.65 to $38.09, inclusive. 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.
4. These options are currently vested.
/s/ Gregory R. Packer, as Attorney-in-Fact 06/23/2025
** Signature of Reporting Person Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

Source: View Original Filing on SEC EDGAR

FAQ

What insider trading activity occurred at WAY on June 20, 2025?

On June 20, 2025, Eric L. Sinclair III (Chief Business Officer) exercised 9,702 stock options at $4.14 per share and subsequently sold the same number of shares at an average price of $37.7877 per share. After these transactions, he owned 490,870 shares directly.

How many WAY shares does Eric Sinclair own after his June 2025 transactions?

Following the reported transactions, Eric Sinclair (CBO) owns 490,870 shares directly, which includes unvested RSUs. He also maintains 126,118 stock options with an exercise price of $4.14 that expire on November 1, 2027.

Was WAY insider Sinclair's stock sale planned or spontaneous?

The transactions were pre-planned, occurring automatically pursuant to a Rule 10b5-1 trading plan that Sinclair adopted on February 19, 2025. This type of plan provides an affirmative defense against insider trading allegations by establishing the trade parameters in advance.

What was the price range for WAY shares sold by Eric Sinclair?

Eric Sinclair sold WAY shares in multiple transactions at prices ranging from $37.65 to $38.09 per share, with a weighted average sale price of $37.7877 per share.

How many stock options does WAY's CBO still have after the June 2025 transaction?

After exercising 9,702 options, WAY's Chief Business Officer Eric Sinclair still holds 126,118 vested stock options with an exercise price of $4.14 that expire on November 1, 2027.