CHGG Insider Filing: Daniel Rosensweig Withholds 6,337 Shares to Cover Taxes

Rhea-AI Filing Summary

Daniel Rosensweig, Executive Chairman of Chegg, Inc. (CHGG), reported a transaction dated 09/12/2025 in which 6,337 common shares were disposed of at a price of $1.54 per share. The filing states these shares were automatically withheld by the issuer to satisfy federal and state tax withholding obligations arising from the vesting and settlement of restricted stock units; the Reporting Person did not sell the shares on the open market. After the transaction, the Reporting Person directly beneficially owns 2,031,412 shares and indirectly holds 25,000 and 48,842 shares through two family trusts where he is a co-trustee. The form was signed by an attorney-in-fact on behalf of Mr. Rosensweig on 09/15/2025.

Positive

• High retained ownership: Reporting Person continues to directly own 2,031,412 shares, indicating significant ongoing stake.

Negative

• None.

Insights

Corporate Governance Expert

TL;DR: Routine tax-withholding disposition; large residual ownership maintains alignment with shareholders.

The Form 4 documents an exempt transaction where shares were withheld to cover tax obligations tied to RSU vesting rather than an open-market sale. Such withholdings are standard and do not indicate active divestiture intent. The Reporting Person retains direct beneficial ownership of over two million shares, which implies continued alignment with shareholder interests and ongoing exposure to the company’s performance. No derivative transactions or additional sales are reported.

Securities Compliance Analyst

TL;DR: Filing complies with Section 16 reporting norms; disclosure is clear about the exempt nature of the transaction.

The filing specifies an exempt transaction under Section 16b-3(e) for tax withholding; it properly discloses the number of shares withheld, the price used for withholding, and the remaining direct and indirect holdings. The presence of trusts and co-trustee roles is transparently noted. From a compliance perspective, the form contains the required information and a signed attestation by an attorney-in-fact.

Insider Trade Summary

3 transactions reported

Mixed 3 txns

Insider ROSENSWEIG DANIEL

Role EXECUTIVE CHAIRMAN

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	6,337	$1.54	$10K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 2,031,412 shares (Direct); Common Stock — 25,000 shares (Indirect, See footnote.)

Footnotes (1)

1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing. Held by The Rosensweig Family Revocable Trust U/A/D 03-12-07 where the Reporting Person is a Co-Trustee. Held by The Rosensweig 2012 Irrevocable Children's Trust U/A/D 11-06-12 where the Reporting Person is a Co-Trustee.

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).

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^*

ROSENSWEIG DANIEL

(Last) (First) (Middle)

C/O CHEGG, INC

3990 FREEDOM CIR

(Street)

SANTA CLARA CA 95054

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
CHEGG, INC [ CHGG ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
09/12/2025

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	09/12/2025		F(1)		6,337	D	$1.54	2,031,412	D
Common Stock								25,000	I	See footnote.(2)
Common Stock								48,842	I	See footnote.(3)

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

Explanation of Responses:

1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

2. Held by The Rosensweig Family Revocable Trust U/A/D 03-12-07 where the Reporting Person is a Co-Trustee.

3. Held by The Rosensweig 2012 Irrevocable Children's Trust U/A/D 11-06-12 where the Reporting Person is a Co-Trustee.

Remarks:

	/s/ Damon Nakamura, Attorney-in-Fact for Daniel Rosensweig	09/15/2025
	** 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.

FAQ

What did Daniel Rosensweig report on the Form 4 for CHGG?

He reported that 6,337 common shares were disposed of on 09/12/2025 via withholding to satisfy tax obligations related to RSU vesting.

Did the Form 4 show an open-market sale by the insider?

No. The filing states the shares were automatically withheld by the issuer to satisfy tax withholding and were cancelled, not sold on the open market.

How many CHGG shares does the Reporting Person own after the transaction?

After the transaction the Reporting Person directly beneficially owns 2,031,412 shares and indirectly holds 25,000 and 48,842 shares through trusts.

What exemption covered the transaction reported on the Form 4?

The transaction was reported as an exempt transaction pursuant to Section 16b-3(e) for payment of exercise price or tax liability by delivering or withholding securities incident to RSU vesting.

Who signed the Form 4 on behalf of Daniel Rosensweig?

The form was signed by /s/ Damon Nakamura, Attorney-in-Fact for Daniel Rosensweig on 09/15/2025.