Sinclair III Eric L. (Ric) 4

Accession 0001998250-26-000002

CIK 0001990354other

Filed

Jan 21, 7:00 PM ET

Accepted

Jan 22, 4:14 PM ET

Size

12.8 KB

Accession

0001998250-26-000002

AI-generated summary of this filing

Updated Jan 22, 2026

Waystar (WAY) CBO Ric Sinclair Sells 40,225 Shares After Exercising Options

What Happened

Ric (Eric L.) Sinclair, Chief Business Officer of Waystar Holding Corp. (WAY), exercised stock options to acquire a total of 40,225 shares (7,562 shares at $18.19 and 32,663 shares at $4.14) and then sold 40,225 shares in the open market on January 20, 2026. The exercise cost was $272,778 in the aggregate (7,562×$18.19 + 32,663×$4.14) and the sale generated gross proceeds of about $1,210,077 (weighted average sale price $30.08), before fees and taxes.

Key Details

Transaction date: January 20, 2026; Form 4 filed January 22, 2026 (appears timely — within the 2-business-day reporting window).
Option exercises (code M): 7,562 shares @ $18.19 (acquired), 32,663 shares @ $4.14 (acquired).
Open-market sale (code S): 40,225 shares sold at a weighted average price of $30.08 (range $30.00–$30.23 per footnote).
Derivative disposal entries at $0.00 reflect conversion/settlement of the options upon exercise (not additional cash sales).
Filing notes that these trades occurred automatically under a 10b5-1 plan adopted August 24, 2025 (footnote F2).
Ownership after the transaction is not specified in the provided summary; footnote F1 indicates reported holdings include unvested RSUs. Footnotes F4/F5 describe option grant and vesting status (some performance-vested; options are currently vested).

Context

This was effectively a cashless outcome: Sinclair exercised vested options (paying the exercise prices) and sold the resulting shares the same day. Such paired exercise-and-sell transactions are common for insiders monetizing vested option gains and, when done under a 10b5-1 plan, are pre-arranged and automatic rather than discretionary.

Form 4

Period: 2026-01-20

Chief Business Officer

Transactions

Exercise/Conversion
Common Stock
[F1][F2]
2026-01-20$18.19/sh+7,562$137,553→ 482,388 total
Exercise/Conversion
Common Stock
[F1][F2]
2026-01-20$4.14/sh+32,663$135,225→ 515,051 total
Sale
Common Stock
[F3][F1][F2]
2026-01-20$30.08/sh−40,225$1,210,077→ 474,826 total
Exercise/Conversion
Stock Options (right to buy)
[F4]
2026-01-20−7,562→ 173,938 total
Exercise: $18.19Exp: 2030-08-09→ Common Stock (7,562 underlying)
Exercise/Conversion
Stock Options (right to buy)
[F5]
2026-01-20−32,663→ 6,141 total
Exercise: $4.14Exp: 2027-11-01→ Common Stock (32,663 underlying)

Footnotes (5)

[F1]Includes unvested RSUs.
[F2]These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on August 24, 2025 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).
[F3]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 $30.00 to $30.23, 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.
[F4]Options granted on August 9, 2020 of which 50% of the option vests in five substantially equal annual installments commencing on August 9, 2021 and the remaining 50% of the option vests upon achievement of certain specified performance-based vesting criteria.
[F5]These options are currently vested.

Signature

/s/ Gregory R. Packer, as Attorney-in-Fact|2026-01-22

1 file

Waystar Holding Corp.

CIK 0001990354

Entity typeother