Insider Trading activities at Chegg, Inc (CHGG)

Insider trading activities (stock purchases, sales, and option exercises) reported by insiders of Chegg, Inc (CHGG) since 2014 are shown in Table 1 and Table 2. Table 1 shows the monthly insider trading data of Chegg, Inc. Table 2 shows the detailed insider transactions. This company's CIK number is 1364954.

Total stock buying since 2014: $2,146,793.
Total stock sales since 2014: $389,567,662.
Total stock option exercises since 2014: $57,115,325.


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20 insiders reported insider trading activities at Chegg, Inc (CHGG):
Insider trading activities of Borders Dave Jr.
Insider trading activities of Budig Renee Varni
Insider trading activities of Sarnoff Richard
Insider trading activities of Rosensweig Daniel
Insider trading activities of York John E.
Insider trading activities of Brown Andrew J
Insider trading activities of Schultz Nathan J.
Insider trading activities of Geiger Charles
Insider trading activities of Schlein Ted
Insider trading activities of Brandemuehl Jenny
Insider trading activities of Lem Esther
Insider trading activities of Tzar Kai Richard Li
Insider trading activities of Tomasello Robin
Insider trading activities of Osier Michael A.
Insider trading activities of Housenbold Jeffrey T
Insider trading activities of Levine Marne L.
Insider trading activities of Leblanc Paul
Insider trading activities of Dwane Anne M.
Insider trading activities of Chesnut Robert C.
Insider trading activities of Fillmore John Paul

Table 1. Yearly summary of insider stock purchases, sales, and option exercises at Chegg, Inc (CHGG).
Insider Buying Insider Sales Option Exercises
Year Shares Value Shares Value Shares Value
2025 0 $0 27,973 $39,553 0 $0
2023 0 $0 37,716 $485,796 36,041 $303,285
2022 0 $0 12,890 $360,920 0 $0
2021 60,470 $1,722,063 493,668 $47,675,959 165,135 $1,486,323
2020 1,189 $99,923 1,328,404 $74,890,897 611,818 $5,736,683
2019 0 $0 4,065,503 $157,026,540 2,691,815 $25,934,012
2018 0 $0 3,323,683 $81,174,030 2,348,892 $19,775,134
2017 0 $0 1,818,716 $25,260,720 937,591 $3,820,308
2016 78,842 $324,807 144,334 $912,908 0 $0
2015 0 $0 32,062 $272,312 1,116,679 $59,580
2014 0 $0 177,835 $1,468,027 0 $0

Table 2. Monthly summary of insider trading at Chegg, Inc (CHGG).
Trading Period Insider Buying Insider Sales Option Exercises
year-month Shares Value Shares Value Shares Value
2025-06 0 $0 27,973 $39,553 0 $0
2023-12 0 $0 1,980 $20,435 0 $0
2023-11 0 $0 16,921 $169,548 0 $0
2023-09 0 $0 2,365 $24,233 0 $0
2023-06 0 $0 2,569 $26,639 0 $0
2023-05 0 $0 0 $0 36,041 $303,285
2023-03 0 $0 9,741 $159,335 0 $0
2023-02 0 $0 4,140 $85,606 0 $0
2022-11 0 $0 12,890 $360,920 0 $0
2021-12 60,470 $1,722,063 0 $0 145,421 $1,305,940
2021-04 0 $0 79,714 $7,424,562 19,714 $180,383
2021-03 0 $0 85,954 $7,834,521 0 $0
2021-02 0 $0 300,000 $29,865,600 0 $0
2021-01 0 $0 28,000 $2,551,276 0 $0
2020-12 0 $0 114,042 $9,988,233 82,458 $1,030,725
2020-11 0 $0 60,016 $4,265,463 0 $0
2020-10 0 $0 38,000 $3,036,520 10,000 $76,500
2020-09 0 $0 31,584 $2,125,174 0 $0
2020-08 1,189 $99,923 28,000 $2,369,080 0 $0
2020-07 0 $0 120,459 $9,288,396 92,459 $1,104,187
2020-06 0 $0 66,667 $4,499,150 35,083 $438,537
2020-05 0 $0 191,484 $12,174,842 114,042 $1,117,194
2020-04 0 $0 63,923 $2,327,740 14,375 $107,215
2020-03 0 $0 181,392 $6,901,865 0 $0

Table 3. Detailed insider trading at Chegg, Inc (CHGG)
  Trade Date   Insider Name Trade Type     Shares       Price ($)   Value ($)
2025-06-06 Budig Renee Varni (Director) Sale 27,973 1.41 39,553
2023-12-13 Schultz Nathan J. (CHIEF OPERATING OFFICER) Sale 1,350 10.41 14,054
2023-12-04 Schultz Nathan J. (CHIEF OPERATING OFFICER) Sale 630 10.13 6,381
2023-11-27 Brown Andrew J (CHIEF FINANCIAL OFFICER) Sale 16,921 10.02 169,548
2023-09-13 Schultz Nathan J. (CHIEF OPERATING OFFICER) Sale 1,547 10.06 15,562
2023-09-05 Schultz Nathan J. (CHIEF OPERATING OFFICER) Sale 818 10.60 8,671
2023-06-14 Schultz Nathan J. (CHIEF OPERATING OFFICER) Sale 1,751 10.75 18,823
2023-06-05 Schultz Nathan J. (CHIEF OPERATING OFFICER) Sale 818 9.56 7,816
2023-05-12 Levine Marne L. Option Ex 36,041 8.41 303,285
2023-03-06 Lem Esther (CHIEF MARKETING OFFICER) Sale 5,700 16.86 96,130
2023-03-02 Schultz Nathan J. (Chief Operating Officer) Sale 4,041 15.64 63,205
2023-02-01 Schultz Nathan J. (Chief Operating Officer) Sale 4,140 20.68 85,606
2022-11-15 Leblanc Paul Sale 12,890 28.00 360,920
2021-12-09 Sarnoff Richard Option Ex 136,921 9.06 1,240,915
2021-12-03 York John E. Option Ex 8,500 7.65 65,025
2021-12-02 Schlein Ted Buy 35,470 28.54 1,012,313
2021-12-01 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Buy 25,000 28.39 709,750
2021-04-26 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 30,000 95.26 2,857,800
2021-04-23 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 30,000 92.86 2,785,800
2021-04-13 Fillmore John Paul (PRESIDENT, CHEGG SKILLS) Sale 19,714 90.34 1,780,962
2021-04-13 Fillmore John Paul (PRESIDENT, CHEGG SKILLS) Option Ex 19,714 9.15 180,383
2021-03-15 Lem Esther (CHIEF MARKETING OFFICER) Sale 34,449 89.50 3,083,185
2021-03-03 Fillmore John Paul (PRESIDENT, CHEGG SKILLS) Sale 51,505 92.25 4,751,336
2021-02-22 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 300,000 99.55 29,865,600
2021-01-07 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 91.12 2,551,276
2020-12-21 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 82,458 90.20 7,437,711
2020-12-21 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Option Ex 82,458 12.50 1,030,725
2020-12-11 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 81.33 2,277,240
2020-12-03 Fillmore John Paul (PRESIDENT, CHEGG SKILLS) Sale 1,321 75.55 99,801
2020-12-03 Lem Esther (CHIEF MARKETING OFFICER) Sale 2,263 76.66 173,481
2020-11-20 Tomasello Robin (VP, CORPORATE CONTROLLER) Sale 32,016 71.45 2,287,543
2020-11-19 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 70.64 1,977,920
2020-10-12 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 82.24 2,302,720
2020-10-01 York John E. Sale 10,000 73.38 733,800
2020-10-01 York John E. Option Ex 10,000 7.65 76,500
2020-09-22 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 66.26 1,855,280
2020-09-03 Lem Esther (CHIEF MARKETING OFFICER) Sale 2,263 73.89 167,213
2020-09-02 Fillmore John Paul (CHIEF STRATEGY OFFICER) Sale 1,321 77.73 102,681
2020-08-06 Leblanc Paul Buy 1,189 84.04 99,923
2020-08-05 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 84.61 2,369,080
2020-07-31 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 82,459 80.34 6,624,756
2020-07-31 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Option Ex 82,459 12.50 1,030,737
2020-07-07 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 70.83 1,983,240
2020-07-01 York John E. Sale 10,000 68.04 680,400
2020-07-01 York John E. Option Ex 10,000 7.34 73,450
2020-06-29 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 64.84 1,815,520
2020-06-22 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 35,083 70.19 2,462,475
2020-06-22 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Option Ex 35,083 12.50 438,537
2020-06-03 Fillmore John Paul (CHIEF STRATEGY OFFICER) Sale 1,321 62.30 82,298
2020-06-03 Lem Esther (CHIEF MARKETING OFFICER) Sale 2,263 61.36 138,857
2020-05-18 Fillmore John Paul (CHIEF STRATEGY OFFICER) Sale 49,442 64.85 3,206,313
2020-05-14 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 63.81 1,786,680
2020-05-13 Sarnoff Richard Sale 66,666 65.09 4,339,289
2020-05-13 Sarnoff Richard Option Ex 66,666 7.88 524,994
2020-05-05 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 47,376 60.00 2,842,560
2020-05-05 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Option Ex 47,376 12.50 592,200
2020-04-17 Levine Marne L. Sale 4,375 36.37 159,118
2020-04-17 Levine Marne L. Option Ex 4,375 8.41 36,815
2020-04-13 Lem Esther (CHIEF MARKETING OFFICER) Sale 21,548 37.03 797,922
2020-04-09 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 28,000 36.65 1,026,200
2020-04-01 York John E. Sale 10,000 34.45 344,500
2020-04-01 York John E. Option Ex 10,000 7.04 70,400
2020-03-16 Lem Esther (CHIEF MARKETING OFFICER) Sale 54,528 32.89 1,793,425
2020-03-05 Brown Andrew J (CHIEF FINANCIAL OFFICER) Sale 16,542 40.06 662,672
2020-03-04 Brown Andrew J (CHIEF FINANCIAL OFFICER) Sale 980 40.00 39,200
2020-03-03 Brown Andrew J (CHIEF FINANCIAL OFFICER) Sale 86,000 40.32 3,467,520
2020-03-01 Fillmore John Paul (CHIEF BUSINESS OFFICER) Sale 23,342 40.23 939,048
2020-02-25 Fillmore John Paul (CHIEF BUSINESS OFFICER) Sale 14,473 37.74 546,211
2020-02-24 Lem Esther (CHIEF MARKETING OFFICER) Sale 15,045 38.65 581,489
2020-02-24 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 35,864 38.63 1,385,426
2020-02-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 48,669 40.64 1,977,908
2020-02-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 48,669 6.92 336,546
2020-02-10 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 24,000 44.24 1,061,760
2020-02-03 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 41.68 277,463
2020-01-22 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 8,000 43.74 349,920
2020-01-21 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 150,000 43.02 6,453,000
2020-01-21 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 150,000 6.92 1,037,250
2020-01-17 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 30,057 43.27 1,300,476
2020-01-17 Levine Marne L. Sale 13,125 42.85 562,406
2020-01-17 Levine Marne L. Option Ex 13,125 8.41 110,446
2020-01-13 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 22,568 41.04 926,123
2020-01-08 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 6,115 40.26 246,189
2020-01-06 York John E. Sale 10,000 38.82 388,200
2020-01-06 York John E. Option Ex 10,000 7.04 70,400
2020-01-02 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 38.33 255,162
2020-01-02 Lem Esther (CHIEF MARKETING OFFICER) Sale 41,607 38.52 1,602,701
2020-01-02 Lem Esther (CHIEF MARKETING OFFICER) Option Ex 41,607 7.39 307,683
2019-12-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 150,000 38.36 5,754,000
2019-12-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 150,000 6.92 1,037,250
2019-12-12 Tomasello Robin (VP, CORPORATE CONTROLLER) Sale 9,406 37.02 348,257
2019-12-11 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 107,590 37.38 4,021,714
2019-12-02 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 38.84 258,557
2019-12-02 Lem Esther (CHIEF MARKETING OFFICER) Sale 50,000 38.19 1,909,500
2019-12-02 Lem Esther (CHIEF MARKETING OFFICER) Option Ex 50,000 7.88 393,750
2019-11-26 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 13,756 39.26 540,019
2019-11-25 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 13,758 38.25 526,284
2019-11-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 150,000 36.60 5,490,000
2019-11-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 150,000 6.92 1,037,250
2019-11-05 Lem Esther (CHIEF MARKETING OFFICER) Sale 50,000 34.40 1,720,000
2019-11-05 Lem Esther (CHIEF MARKETING OFFICER) Option Ex 50,000 10.19 509,400
2019-11-01 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 30.77 204,835
2019-10-21 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 150,000 32.57 4,885,500
2019-10-21 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 150,000 6.92 1,037,250
2019-10-17 Levine Marne L. Sale 4,375 32.54 142,362
2019-10-17 Levine Marne L. Option Ex 4,375 8.41 36,815
2019-10-11 Lem Esther (CHIEF MARKETING OFFICER) Sale 50,000 32.00 1,600,000
2019-10-11 Lem Esther (CHIEF MARKETING OFFICER) Option Ex 50,000 12.50 625,000
2019-10-01 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 30.09 200,309
2019-10-01 York John E. Sale 12,500 29.55 369,375
2019-10-01 York John E. Option Ex 12,500 7.04 88,000
2019-09-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 150,000 33.35 5,002,500
2019-09-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 150,000 8.78 1,316,550
2019-09-03 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 39.33 261,786
2019-09-03 Lem Esther (CHIEF MARKETING OFFICER) Sale 50,000 39.28 1,964,000
2019-09-03 Lem Esther (CHIEF MARKETING OFFICER) Option Ex 50,000 12.50 625,000
2019-08-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 150,000 40.69 6,103,500
2019-08-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 150,000 12.50 1,875,000
2019-08-13 Brandemuehl Jenny (CHIEF PEOPLE OFFICER) Sale 100,840 41.58 4,192,926
2019-08-06 Brown Andrew J (CHIEF FINANCIAL OFFICER) Sale 43,754 43.02 1,882,297
2019-08-06 Brown Andrew J (CHIEF FINANCIAL OFFICER) Option Ex 43,754 12.50 546,925
2019-08-05 Brown Andrew J (CHIEF FINANCIAL OFFICER) Sale 100,000 42.89 4,289,000
2019-08-05 Brown Andrew J (CHIEF FINANCIAL OFFICER) Option Ex 100,000 12.50 1,250,000
2019-08-02 Brown Andrew J (CHIEF FINANCIAL OFFICER) Option Ex 100,000 12.50 1,250,000
2019-08-01 Fillmore John Paul (CHIEF BUSINESS OFFICER) Sale 14,473 44.71 647,087
2019-08-01 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,654 44.76 297,833
2019-08-01 Lem Esther (CHIEF MARKETING OFFICER) Sale 50,000 44.76 2,238,000
2019-08-01 Lem Esther (CHIEF MARKETING OFFICER) Option Ex 48,020 12.50 600,250
2019-08-01 Brown Andrew J (CHIEF FINANCIAL OFFICER) Sale 200,000 44.82 8,964,000
2019-08-01 Brown Andrew J (CHIEF FINANCIAL OFFICER) Option Ex 100,000 12.50 1,250,000
2019-07-30 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 8,000 46.90 375,200
2019-07-30 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 54,687 47.88 2,618,413
2019-07-30 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Option Ex 54,687 7.88 430,660
2019-07-22 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 158,251 43.06 6,814,288
2019-07-22 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 158,251 10.96 1,734,114
2019-07-17 Levine Marne L. Sale 46,551 44.04 2,050,106
2019-07-17 Levine Marne L. Option Ex 8,750 8.41 73,631
2019-07-15 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 4,000 44.98 179,920
2019-07-08 Osier Michael A. (CIO AND CHIEF OUTCOMES OFFICER) Sale 16,527 42.23 698,017
2019-07-08 Schultz Nathan J. (PRESIDENT OF LEARNING SERVICES) Sale 38,101 42.39 1,615,101
2019-07-01 Fillmore John Paul (CHIEF BUSINESS OFFICER) Sale 20,143 39.45 794,641
2019-07-01 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 39.46 262,685
2019-07-01 Lem Esther (CHIEF MARKETING OFFICER) Sale 50,000 39.46 1,973,000
2019-07-01 York John E. Sale 12,500 39.44 493,000
2019-07-01 York John E. Option Ex 12,500 8.10 101,187
2019-06-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 165,000 39.93 6,588,450
2019-06-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 165,000 10.19 1,681,020
2019-06-03 Borders Dave Jr. (GENERAL COUNSEL) Sale 6,657 36.52 243,113
2019-06-03 Lem Esther (CHIEF MARKETING OFFICER) Sale 50,000 36.33 1,816,500
2019-05-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Sale 165,000 36.55 6,030,420
2019-05-20 Rosensweig Daniel (PRESIDENT, CEO & CO-CHAIRMAN) Option Ex 165,000 10.65 1,757,250
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Insider trading activities including stock purchases, stock sales, and option exercises of CHGG listed in the above tables cannot be completely guaranteed as to their accuracy. For more insider trading information of Chegg, Inc (symbol CHGG, CIK number 1364954) see the Securities and Exchange Commission (SEC) website.



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