• Website:
  • Location: Santa Clara, California
  • Total employees: 361 US full‐time employees, 324 globally
  • Employee demographics: 60 percent Millennials, 40 percent non‐Millennials
  • What it does: Chegg, the Student Hub, offers 24/7 online tutoring, test prep, textbook rentals, and other educational services for high school and college students
  • Interviewee: Dan Rosensweig—Chairman, Chief Executive Officer, President


Based in Silicon Valley, Chegg has tested numerous strategies both to retain employees and to improve the working relationship between generations. Rosensweig refers to Silicon Valley as “the canary in the coal mine” when it comes to companies having to think about a multigenerational workforce and being on the cutting edge of providing corporate perks. He describes the region as a very expensive suburb with little nightlife or culture—which is why younger employees, particularly those without families, choose to live in nearby, vibrant San Francisco.

The company's history of diversity in other areas has allowed it to be vigilant about generational differences. There's a good mix of employees born in the United States and abroad, 44 percent of the staff is female, and its approach toward ethnic diversity is also broadening. Rosensweig explains, “We are trying to be more representative, because the students that we serve are more representative of America versus what corporate America generally looked like. So it's ...

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