CHGG

SEC source: 0001364954-21-000092 · wf-form4_163122073413905.xml · nonDerivative · entry 1

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,197

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.

SEC source: 0001364954-21-000102 · wf-form4_163131471016512.xml · nonDerivative · entry 2

SARNOFF RICHARD · CIK 0001236133 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 70,362

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.

SEC source: 0001364954-21-000102 · wf-form4_163131471016512.xml · nonDerivative · entry 1

SARNOFF RICHARD · CIK 0001236133 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 68,398

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.

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: 0001364954-21-000059 · wf-form4_162277085107863.xml · nonDerivative · entry 4

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 121,344

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: 0001364954-21-000059 · wf-form4_162277085107863.xml · nonDerivative · entry 3

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 126,290

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: 0001364954-21-000063 · wf-form4_162277105802682.xml · nonDerivative · entry 1

TOMASELLO ROBIN · CIK 0001608511 · VP, CORPORATE CONTROLLER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 57,741

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 248 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan ("ESPP") on May 14, 2021.

SEC source: 0001364954-21-000062 · wf-form4_162277101362410.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 143,762

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: 0001364954-21-000062 · wf-form4_162277101362410.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 146,967

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: 0001364954-21-000060 · wf-form4_162277087884775.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 208,154

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: 0001364954-21-000060 · wf-form4_162277087884775.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 213,100

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 324 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan ("ESPP") on May 14, 2021.

SEC source: 0001364954-21-000058 · wf-form4_162277082858476.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 113,038

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: 0001364954-21-000058 · wf-form4_162277082858476.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 116,461

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: 0001364954-21-000038 · wf-form4_161956393989038.xml · nonDerivative · entry 4

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 216,154

F1 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 18, 2021.

F5 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $95.00 to $95.80 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001364954-21-000038 · wf-form4_161956393989038.xml · nonDerivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 246,154

F1 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 18, 2021.

F4 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $93.64 to $93.80 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001364954-21-000038 · wf-form4_161956393989038.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 246,454

F1 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 18, 2021.

F3 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $92.53 to $93.50 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001364954-21-000038 · wf-form4_161956393989038.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 257,127

F1 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 18, 2021.

F2 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $91.53 to $92.52 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001364954-21-000036 · wf-form4_161860536858201.xml · derivative · entry 4

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 19,714 shares

Expires 2023-08-05

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.

F4 · derivative.exercise_date: The stock option was fully vested and exercisable as of June 10, 2017.

SEC source: 0001364954-21-000036 · wf-form4_161860536858201.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 118,432

F1 · kind: The exercise of options and sale of the resultant shares in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on February 12, 2021.

F3 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $90.37 to $91.31 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001364954-21-000036 · wf-form4_161860536858201.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 134,949

F1 · kind: The exercise of options and sale of the resultant shares in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on February 12, 2021.

F2 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $89.16 to $90.00 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001364954-21-000036 · wf-form4_161860536858201.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 138,146

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: 0001364954-21-000030 · wf-form4_161603017474652.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 148,785

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 12, 2020.

F3 · price: This transaction was executed in multiple trades at prices ranging from $89.57 to $90.14; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000030 · wf-form4_161603017474652.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 157,835

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 12, 2020.

F2 · price: This transaction was executed in multiple trades at prices ranging from $88.57 to $89.56; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000059 · wf-form4_162277085107863.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 129,668

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 8

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 118,432

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 7

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 118,932

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

F8 · price: This transaction was executed in multiple trades at prices ranging from $96.41 to $96.42; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 6

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 119,172

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

F7 · price: This transaction was executed in multiple trades at prices ranging from $95.40 to $96.21; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 5

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 123,258

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

F6 · price: This transaction was executed in multiple trades at prices ranging from $91.42 to $91.66; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 4

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 124,998

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

F5 · price: This transaction was executed in multiple trades at prices ranging from $90.33 to $91.30; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 133,417

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

F4 · price: This transaction was executed in multiple trades at prices ranging from $89.33 to $90.31; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 153,459

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

F3 · price: This transaction was executed in multiple trades at prices ranging from $88.32 to $89.31; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 160,159

F1 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

F2 · price: This transaction was executed in multiple trades at prices ranging from $87.32 to $88.31; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000059 · wf-form4_162277085107863.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Indirect · By Andy and Pam Brown Family Trust

Disclosed balance after: 41,836

F1 · ownership.nature: The Reporting Person is a Co-Trustee.

SEC source: 0001364954-21-000024 · wf-form4_161482490866587.xml · nonDerivative · entry 5

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 183,234

F5 · kind: The reported disposition represents a bona fide charitable gift made by the Reporting Person.

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: 0001364954-21-000023 · wf-form4_161482465472327.xml · derivative · entry 6

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 72,935

Underlying: Common Stock · 72,935 shares

Expires 2025-03-01

F5 · 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.

F6 · 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.

F7 · derivative.underlying_shares: Shares represent 150% of the PSUs awarded, the maximum rate of undetermined achievement.

SEC source: 0001364954-21-000023 · wf-form4_161482465472327.xml · nonDerivative · entry 4

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 180,992

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

SEC source: 0001364954-21-000023 · wf-form4_161482465472327.xml · nonDerivative · entry 3

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 210,167

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

SEC source: 0001364954-21-000023 · wf-form4_161482465472327.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 228,474

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 totime-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 eachperformance 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'scontinued service through each vesting date.

SEC source: 0001364954-21-000023 · wf-form4_161482465472327.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 161,527

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 1/3vesting on March 1, 2022 and then the remaining shares vesting in equal quarterly installments thereafter for 24 months.

SEC source: 0001364954-21-000026 · wf-form4_161482602368536.xml · derivative · entry 3

TOMASELLO ROBIN · CIK 0001608511 · VP, CORPORATE CONTROLLER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 14,587

Underlying: Common Stock · 14,587 shares

Expires 2025-03-01

F3 · kind: The PSU award are earned and become vested based upon both (i) attainment of the Absolute TSR Performance Metric and (ii) completion of the service-based vesting dates. The share price will be measured using a 60-day trailing average, with performance assessed quarterly. Once a performance target is met, the shares will become earned and will vest at 50% on the 3rd and 4th anniversary of the award date.

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 PSUsto vest on March 8, 2024 and 50% to vest on March 1, 2025.

F5 · derivative.underlying_shares: Shares represent 150% of the PSUs awarded, the maximum rate of undetermined achievement.

SEC source: 0001364954-21-000026 · wf-form4_161482602368536.xml · nonDerivative · entry 2

TOMASELLO ROBIN · CIK 0001608511 · VP, CORPORATE CONTROLLER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,687

F2 · shares: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of RSUs.

SEC source: 0001364954-21-000026 · wf-form4_161482602368536.xml · nonDerivative · entry 1

TOMASELLO ROBIN · CIK 0001608511 · VP, CORPORATE CONTROLLER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,039

F1 · shares: The restricted stock unit award shall vest over a three-year period with 1/3 of the shares subject to the award vesting on the first anniversary of the award date, and the remaining shares vesting in equal quarterly installments thereafter for 24 months, subject to the employee's continuous service on each of the specified vest dates and to the terms and conditions in the Restricted Stock Unit Agreement.

SEC source: 0001364954-21-000025 · wf-form4_161482509674677.xml · derivative · entry 5

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,348

Underlying: Common Stock · 58,348 shares

Expires 2021-03-01

F5 · 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.

F6 · 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 PSUsto vest on March 8, 2024 and 50% to vest on March 1, 2025.

F7 · derivative.underlying_shares: Shares represent 150% of the PSUs awarded, the maximum rate of undetermined achievement.

SEC source: 0001364954-21-000025 · wf-form4_161482509674677.xml · nonDerivative · entry 4

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 167,937

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