CHGG

SEC source: 0001364954-22-000121 · wf-form4_167027978533675.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 162,194

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: 0001364954-22-000121 · wf-form4_167027978533675.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 164,913

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: 0001364954-22-000120 · wf-form4_167027976183476.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 180,345

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: 0001364954-22-000120 · wf-form4_167027976183476.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 182,900

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: 0001364954-22-000109 · wf-form4_166872271186203.xml · nonDerivative · entry 1

LEBLANC PAUL · CIK 0001770731 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,861

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: 0001364954-22-000092 · wf-form4_166250385506610.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 236,224

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: 0001364954-22-000092 · wf-form4_166250385506610.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 240,017

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: 0001364954-22-000096 · wf-form4_166250419490086.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 269,182

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: 0001364954-22-000096 · wf-form4_166250419490086.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 272,975

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: 0001364954-22-000094 · wf-form4_166250400693743.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 167,013

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: 0001364954-22-000094 · wf-form4_166250400693743.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 169,716

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: 0001364954-22-000095 · wf-form4_166250410697192.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 184,833

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: 0001364954-22-000095 · wf-form4_166250410697192.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 186,616

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: 0001364954-22-000069 · wf-form4_165429495191071.xml · nonDerivative · entry 1

Bond Sarah · CIK 0001816807 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 15,731

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000073 · wf-form4_165429520604362.xml · nonDerivative · entry 1

WHELAN MELANIE ANYA · CIK 0001777980 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 24,530

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000068 · wf-form4_165429485875911.xml · nonDerivative · entry 1

BUDIG RENEE VARNI · CIK 0001658725 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 40,063

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000075 · wf-form4_165429529109884.xml · nonDerivative · entry 1

SCHLEIN TED · CIK 0001242733 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 200,409

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000074 · wf-form4_165429525310655.xml · nonDerivative · entry 2

SARNOFF RICHARD · CIK 0001236133 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,959

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000074 · wf-form4_165429525310655.xml · nonDerivative · entry 1

SARNOFF RICHARD · CIK 0001236133 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 217,955

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting 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: 0001364954-22-000078 · wf-form4_165429552976861.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 242,905

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: 0001364954-22-000078 · wf-form4_165429552976861.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 246,697

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: 0001364954-22-000079 · wf-form4_165429558736419.xml · nonDerivative · entry 1

LEBLANC PAUL · CIK 0001770731 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 24,751

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000077 · wf-form4_165429545493354.xml · nonDerivative · entry 1

Martin Marcela · CIK 0001856602 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,866

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000076 · wf-form4_165429536583748.xml · nonDerivative · entry 1

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,869

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000072 · wf-form4_165429514640504.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 171,563

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: 0001364954-22-000072 · wf-form4_165429514640504.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 173,460

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: 0001364954-22-000071 · wf-form4_165429509302356.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 275,863

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: 0001364954-22-000071 · wf-form4_165429509302356.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 279,655

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. This also includes 454 ESPP shares inadvertently missed on previous filings.

SEC source: 0001364954-22-000070 · wf-form4_165429502284839.xml · nonDerivative · entry 1

York John E. · CIK 0001586638 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 38,583

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-22-000067 · wf-form4_165429481164054.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 188,154

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: 0001364954-22-000067 · wf-form4_165429481164054.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 189,936

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: 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: 0001364954-22-000029 · wf-form4_164867459820088.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 249,584

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: 0001364954-22-000033 · wf-form4_164867500497432.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 190,442

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: 0001364954-22-000031 · wf-form4_164867475538497.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 174,082

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: 0001364954-22-000027 · wf-form4_164867437783650.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 281,246

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: 0001364954-22-000023 · wf-form4_164635648618055.xml · nonDerivative · entry 4

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 96,040

F4 · shares: On March 1, 2022, the Reporting Person transferred 21,625 shares of Common Stock to the Andy and Pam Brown Family Trust where the Reporting Person is a Co-Trustee.

SEC source: 0001364954-22-000023 · wf-form4_164635648618055.xml · nonDerivative · entry 3

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 117,665

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: 0001364954-22-000023 · wf-form4_164635648618055.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 124,242

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: 0001364954-22-000023 · wf-form4_164635648618055.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 129,509

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: 0001364954-22-000022 · wf-form4_164635645808454.xml · nonDerivative · entry 3

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 141,308

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: 0001364954-22-000022 · wf-form4_164635645808454.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 145,483

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: 0001364954-22-000022 · wf-form4_164635645808454.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 148,861

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.