[Form 4] CHEGG, INC Insider Trading Activity

Rhea-AI Filing Summary

Chegg, Inc. reported a new equity award for Executive Chairman and Director Daniel Rosensweig. On 11/17/2025 he received 1,650,000 restricted stock units at a price of $0, each representing one share of common stock. These RSUs begin vesting from a commencement date of 10/28/2025, with one-third vesting after one year and the remainder vesting quarterly over the following two years.

He also received 3,850,000 performance-based restricted stock units granted in 2025 that become eligible to vest after the Compensation Committee determines achievement of specified performance measurements on 10/28/2028. The shares tied to these PSUs vest in four 25% tranches if the stock appreciates by 50%, 75%, 100% and 125%, subject to his continued service through each vesting date. Following these grants, Rosensweig beneficially owned 7,531,412 shares of Chegg common stock directly.

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

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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)
11/17/2025

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	11/17/2025		A(1)		1,650,000	A	$0	3,681,412	D
Common Stock	11/17/2025		A(2)		3,850,000	A	$0	7,531,412	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

Explanation of Responses:

1. Represents an award of restricted stock units ("RSU", and each an "RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU will vest 3yr 1/3rd Cliff after 1-year, quarterly vesting thereafter. Vesting Commencement Date is 10/28/2025

2. Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2025 (the "2025 PSUs") that shall now be subject to vesting following the Compensation Committee's determination of the achievement of certain performance measurements on 10/28/2028. The shares subject to the 2025 PSUs allocated to each performance metric shall vest as follows: 25% shall vest upon the stock appreciation by 50%, and then similarly in same tranches upon stock appreciation by 75%, 100% and 125% respectively with 25% each tranche subject to the Reporting Person's continued service through each vesting date. VCD is 10/28/2025

Remarks:

	/s/ Damon Nakamura, Attorney-in-Fact for Daniel Rosensweig	11/19/2025
	** 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 insider transaction did Chegg (CHGG) report for Daniel Rosensweig?

Chegg reported that Executive Chairman and Director Daniel Rosensweig received new equity awards on 11/17/2025, consisting of both time-based restricted stock units and performance-based restricted stock units.

How many restricted stock units did Daniel Rosensweig receive from Chegg (CHGG)?

Daniel Rosensweig received 1,650,000 time-based restricted stock units of Chegg common stock at a price of $0, each RSU representing a right to receive one share upon vesting.

What are the vesting terms for Daniel Rosensweig’s RSUs at Chegg (CHGG)?

The 1,650,000 RSUs have a vesting commencement date of 10/28/2025. One-third vests after one year, with the remaining two-thirds vesting quarterly over the following two years, subject to continued service.

How many performance-based RSUs (PSUs) did Daniel Rosensweig receive from Chegg (CHGG)?

Daniel Rosensweig received 3,850,000 shares of Chegg common stock subject to performance-based restricted stock units granted in 2025, which become eligible to vest after performance measurement on 10/28/2028.

What performance goals determine vesting of Chegg’s 2025 PSUs for Daniel Rosensweig?

The 2025 PSUs vest based on stock price appreciation: 25% of the shares vest at stock appreciation of 50%, and additional 25% tranches vest at appreciation of 75%, 100%, and 125%, each subject to his continued service.

How many Chegg (CHGG) shares does Daniel Rosensweig beneficially own after these awards?

After the reported transactions, Daniel Rosensweig beneficially owned 7,531,412 shares of Chegg common stock held directly.

What is Daniel Rosensweig’s role at Chegg (CHGG) as shown in this filing?

Daniel Rosensweig is identified as both a Director and an Officer of Chegg, serving as Executive Chairman.