[Form 4] Oscar Health, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Skillz Inc. (NYSE: SKLZ) disclosed in an 8-K that its Board appointed Todd A. Valli as Chief Accounting Officer, effective 14 July 2025. Valli, 51, spent the last 14 years in senior finance roles at Everi Holdings Inc., most recently as SVP Corporate Finance, Tax & CAO. His hire fills the registrant’s principal accounting leadership slot.

• Base salary: US$325,000 per year
• Annual cash bonus target: US$115,000 (pro-rated for 2025, performance-based)
• Annual equity: US$100,000 time-based RSUs (1-year cliff) + US$100,000 PSUs (1-year, performance-linked)
• Contingency: Equity grants and Valli’s designation as principal accounting officer take effect once the company becomes current with its Exchange Act filings.
• No family relationships or related-party transactions were reported.

The move strengthens accounting oversight but also signals that Skillz is not yet current with periodic SEC filings, a compliance overhang investors should note.

Insights

Financial Analyst

TL;DR: Veteran CAO hire adds finance depth; impact muted until delayed filings resolved; net neutral.

Valli’s 14-year track record managing audit, tax and SEC reporting for a listed gaming supplier should bolster Skillz’s internal controls and credibility with lenders and investors. However, all equity awards—and his formal role as principal accounting officer—are conditional on Skillz becoming current with its reports, confirming the company is still out of compliance. Until the backlog is cleared, capital-market access and investor confidence remain constrained, making this disclosure strategically important but not immediately value-accretive.

Corporate Governance Expert

TL;DR: Governance positive from seasoned hire, but compliance lapse tempers benefit; overall neutral.

Appointing a dedicated CAO aligns with governance best practices, especially for growth-stage tech firms with complex revenue recognition. Compensation is balanced between fixed pay and performance-linked equity, encouraging alignment with shareholders. Nevertheless, postponing the equity grant until SEC compliance is regained underscores governance risk: current filings are overdue, which may expose the board to additional scrutiny. The appointment is a step toward remediation, yet governance scores will not improve until timely reporting is restored.

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).

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^*

Gassen William

(Last) (First) (Middle)

75 VARICK STREET, 5TH FLOOR

(Street)

NEW YORK NY 10013

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Oscar Health, Inc. [ OSCR ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
07/10/2025

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

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
Deferred Stock Unit	(1)	07/10/2025		A		1,215		(3)	(3)	Class A Common Stock	1,215	$15.53(2)	2,745	D

Explanation of Responses:

1. Each deferred stock unit represents a right to receive one share of the Issuer's Class A common stock.

2. The Reporting Person elected, pursuant to the Issuer's Amended and Restated Deferred Compensation Plan for Directors, to receive deferred stock units in lieu of cash retainer payments for service on the Issuer's board of directors. The price of the deferred stock units reported herein represents the closing price of the Issuer's Class A common stock on July 10, 2025, which price was used to calculate the number of deferred stock units issued to the Reporting Person.

3. The deferred stock units will be settled for cash or shares of Class A common stock, in the Issuer's discretion, within 45 days of the first to occur of (i) termination of service; (ii) a change in control; (iii) death; or (iv) disability. Deferred stock units issued in lieu of a cash retainer payment are 100% vested on the grant date.

Remarks:

	/s/ Melissa Curtin, Attorney-in-Fact	07/14/2025
	** 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.