ROSENSWEIG DANIEL

SEC source: 0001364954-23-000086 · wk-form4_1686003230.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,893,649

F3 · kind: 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 agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-23-000086 · wk-form4_1686003230.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,895,761

F1 · kind: 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.

F2 · balance_after: Includes 876 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2023.

SEC source: 0000796343-23-000105 · wf-form4_168237024044027.xml · derivative · entry 4

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 836

Underlying: Common Stock · 836 shares

Expires not disclosed

F3 · derivative.exercise_date: Vests 100% on the day of the Issuer's next annual meeting of stockholders.

F3 · derivative.expiration_date: Vests 100% on the day of the Issuer's next annual meeting of stockholders.

SEC source: 0000796343-23-000105 · wf-form4_168237024044027.xml · derivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 672 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: This restricted stock unit award vested in full on April 20, 2023.

F2 · derivative.expiration_date: This restricted stock unit award vested in full on April 20, 2023.

SEC source: 0000796343-23-000105 · wf-form4_168237024044027.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,537

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001364954-23-000046 · wf-form4_168013526727137.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,897,033

F1 · shares: Represents an award of restricted stock units ("RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU award vests with respect to 100% of the shares subject to the RSU on March 12, 2024 (the "Vesting Date"), subject to recipient's continued service up to and through the Vesting Date.

SEC source: 0001364954-23-000035 · wf-form4_167883850306049.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,781,657

F3 · kind: 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 agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-23-000035 · wf-form4_167883850306049.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,788,950

F2 · kind: 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.

SEC source: 0001364954-23-000035 · wf-form4_167883850306049.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,812,811

F1 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2022 (the "2022 PSUs") that shall now be subject to time-based vesting following the Compensation Committee's review of the achievement of certain performance measurements on February 8, 2023. The shares subject to the 2022 PSUs allocated to each performance metric shall vest as follows: 1/3 vested on March 12, 2023, and then the remaining 2/3rds shall vest in equal quarterly installments over the next 24 months, subject to the Reporting Person's continued service through each vesting date.

SEC source: 0001364954-23-000021 · wf-form4_167788624991528.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,752,123

F2 · kind: 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 performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-23-000021 · wf-form4_167788624991528.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,757,916

F1 · kind: 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.

SEC source: 0001364954-22-000122 · wf-form4_167027981087537.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,762,307

F2 · kind: 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 performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-22-000122 · wf-form4_167027981087537.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,770,523

F1 · kind: 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.

SEC source: 0001364954-22-000097 · wf-form4_166250429789124.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,776,740

F2 · kind: 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 performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-22-000097 · wf-form4_166250429789124.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,784,956

F1 · kind: 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.

SEC source: 0001468327-22-000083 · wf-form4_165792166893217.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,440

F1 · shares: This is an award of restricted stock units ("RSUs"), each of which represents a contingent right to receive one share of the Issuer's Class A Common Stock. This award is granted as part of the Reporting Person's annual equity award under the Company's Non-employee Director Compensation Program. 100% of this award will vest on the earlier of 1) the one year anniversary of the grant date or 2) the date of the next Annual Meeting of Stockholders, subject to the Reporting Person's continuous service as a member of the Board of Directors on such date.

SEC source: 0001364954-22-000080 · wf-form4_165429565129119.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,791,173

F3 · kind: 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 performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-22-000080 · wf-form4_165429565129119.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,799,389

F1 · kind: 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.

F2 · balance_after: Includes 842 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2022.

SEC source: 0000796343-22-000120 · wf-form4_165032314218982.xml · derivative · entry 4

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 672

Underlying: Common Stock · 672 shares

Expires not disclosed

F3 · derivative.exercise_date: Vests 100% on the day of the Issuer's next annual meeting of stockholders.

F3 · derivative.expiration_date: Vests 100% on the day of the Issuer's next annual meeting of stockholders.

SEC source: 0000796343-22-000120 · wf-form4_165032314218982.xml · derivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 615 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: This restricted stock unit award vested in full on April 14, 2022.

F2 · derivative.expiration_date: This restricted stock unit award vested in full on April 14, 2022.

SEC source: 0000796343-22-000120 · wf-form4_165032314218982.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,865

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001364954-22-000035 · wf-form4_164867514909554.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,804,764

F1 · shares: Represents an award of restricted stock units ("RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU will vest over a 3-year period with 1/3 vesting on March 12, 2023 and then the remaining shares vesting in equal quarterly installments thereafter for 24 months.

SEC source: 0001364954-22-000025 · wf-form4_164635653778846.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,651,219

F3 · kind: 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 agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-22-000025 · wf-form4_164635653778846.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,666,626

F2 · kind: 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.

SEC source: 0001364954-22-000025 · wf-form4_164635653778846.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,682,706

F1 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2021 (the "2021 PSUs") that shall now be subject to time-based vesting following the Compensation Committee's determination of the achievement of certain performance measurements on February 28, 2022. The shares subject to the 2021 PSUs allocated to each performance metric shall vest as follows: 1/3 shall vest on March 1, 2022, and then the remaining 2/3rds shall vest in equal quarterly installments over the next 24 months, subject to the Reporting Person's continued service through each vesting date.

SEC source: 0001364954-21-000124 · wf-form4_163840131953435.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote.

Disclosed balance after: 49,000

F3 · price: The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $28.42 to $29.35 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any stockholder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares and prices at which the transactions were effected within the range set forth in this footnote.

F2 · ownership.nature: Held by Daniel L and Linda Rosensweig, Co-Trustees of the Rosensweig Family Revocable Trust U/A/D 03-12-07. The Reporting Person is a Co-Trustee.

SEC source: 0001364954-21-000124 · wf-form4_163840131953435.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote.

Disclosed balance after: 32,741

F1 · price: The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $27.42 to $28.41 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any stockholder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares and prices at which the transactions were effected within the range set forth in this footnote.

F2 · ownership.nature: Held by Daniel L and Linda Rosensweig, Co-Trustees of the Rosensweig Family Revocable Trust U/A/D 03-12-07. The Reporting Person is a Co-Trustee.

SEC source: 0001364954-21-000140 · wf-form4_163858086104217.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,633,073

F2 · kind: 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 performance stock units (PSUs) to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-21-000140 · wf-form4_163858086104217.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,644,486

F1 · kind: 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.

SEC source: 0000899243-21-042542 · doc4.xml · derivative · entry 7

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 9,334

Underlying: Class A Common Stock · 9,334 shares

Expires 2029-07-02

F1 · kind: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

F2 · derivative.exercise_date: The option vests and becomes exercisable as to 25% of the underlying shares on July 3, 2020 and in 36 substantially equal monthly installments thereafter.

SEC source: 0000899243-21-042542 · doc4.xml · derivative · entry 6

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 9,334 shares

Expires 2029-07-02

F1 · kind: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

F2 · derivative.exercise_date: The option vests and becomes exercisable as to 25% of the underlying shares on July 3, 2020 and in 36 substantially equal monthly installments thereafter.

SEC source: 0000899243-21-042542 · doc4.xml · nonDerivative · entry 5

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Held by The Rosensweig 2012 Irrevocable Children's Trust

Disclosed balance after: 3,229

F1 · kind: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

F1 · price: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

SEC source: 0000899243-21-042542 · doc4.xml · nonDerivative · entry 4

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Held by The Rosensweig 2012 Irrevocable Children's Trust

Disclosed balance after: 0

F1 · kind: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

F1 · price: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

SEC source: 0000899243-21-042542 · doc4.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 50,628

SEC source: 0000899243-21-042542 · doc4.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 45,682

F1 · kind: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

F1 · price: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

SEC source: 0000899243-21-042542 · doc4.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

F1 · price: Immediately prior to the completion of the Issuer's initial public offering, each share of Common Stock was reclassified into one share of Class A Common Stock in an exempt transaction pursuant to Rule 16b-7.

SEC source: 0001364954-21-000087 · wf-form4_163070660708092.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,652,281

F2 · kind: 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 performance stock units (PSUs) to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-21-000087 · wf-form4_163070660708092.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,663,694

F1 · kind: 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.

SEC source: 0001364954-21-000061 · wf-form4_162277089542873.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,671,490

F3 · kind: 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 performance stock units (PSUs) to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. 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.

SEC source: 0001364954-21-000061 · wf-form4_162277089542873.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,682,033

F1 · kind: 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.

F2 · balance_after: Includes 368 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan ("ESPP") on May 14, 2021.

SEC source: 0000796343-21-000103 · wf-form4_161903677495465.xml · derivative · entry 4

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 615

Underlying: Common Stock · 615 shares

Expires not disclosed

F3 · derivative.exercise_date: Vests 100% on the day of the Issuer's next annual meeting of stockholders.

F3 · derivative.expiration_date: Vests 100% on the day of the Issuer's next annual meeting of stockholders.

SEC source: 0000796343-21-000103 · wf-form4_161903677495465.xml · derivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 924 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: This restricted stock unit award vested in full on April 19, 2021

F2 · derivative.expiration_date: This restricted stock unit award vested in full on April 19, 2021

SEC source: 0000796343-21-000103 · wf-form4_161903677495465.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · by trust

Disclosed balance after: 14,028

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · ownership.nature: Includes 11,760 shares held by the Rosensweig Family Revocable Trust of which reporting person is a trustee, and 2,268 shares in trust for the benefit of Mr. Rosensweig's children.

SEC source: 0001364954-21-000022 · wf-form4_161482463144105.xml · derivative · entry 7

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 145,871

Underlying: Common Stock · 145,871 shares

Expires 2025-03-01

F7 · kind: The PSU represents the contingent right to receive, following vesting, between 0% and 150% of one share of common stock based upon the achievement of pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F8 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUs to vest on March 8, 2024 and 50% to vest on March 1, 2025.

F9 · derivative.underlying_shares: Shares represent 150% of the PSUs awarded, the maximum rate of undetermined achievement.

SEC source: 0001364954-21-000022 · wf-form4_161482463144105.xml · nonDerivative · entry 4

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,688,866

F4 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of PSUs.

SEC source: 0001364954-21-000022 · wf-form4_161482463144105.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,755,027

F3 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of RSUs.

SEC source: 0001364954-21-000022 · wf-form4_161482463144105.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,801,028

F2 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2020 (the "2020 PSUs") that shall now be subject to time-based vesting following the Compensation Committee's determination of the achievement of certain performance measurements on February 27, 2021. The shares subject to the 2020 PSUs allocated to each performance metric shall vest as follows: 1/3 shall vest on March 1, 2021, and then the remaining 2/3rds shall vest in equal quarterly installments over the next 24 months, subject to the Reporting Person's continued service through each vesting date.

SEC source: 0001364954-21-000022 · wf-form4_161482463144105.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,657,570

F1 · shares: Represents an award of restricted stock units ("RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU will vest over a 3-year period with 1/3 vesting on March 1, 2022 and then the remaining shares vesting in equal quarterly installments thereafter for 24 months.

SEC source: 0001364954-21-000040 · wf-form4a_161956610159030.xml · derivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 145,871

Underlying: Common Stock · 145,871 shares

Expires 2025-03-01

F1 · derivative.exercise_price: Each Performance Stock Unit ("PSU") represents the contingent right to receive, following vesting, between 0% and 150% of one share of Common Stock based upon the achievement of a pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F2 · shares: This amendment to Form 4 filed on March 3, 2021 is filed to correct the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0 and should have reflected 145,871 PSUs.

F3 · shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F4 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUs to vest on March 8, 2024 and 50% to vest on March 1, 2025.

F3 · derivative.underlying_shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F3 · balance_after: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

SEC source: 0001364954-21-000016 · wf-form4_161412150906892.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,607,090

F1 · kind: The shares were sold in a public offering of the Issuer's common stock to the underwriters who were given an option to purchase additional shares from Mr. Rosensweig.

F2 · price: Represents the net price per share. The gross price per share was $102.00.