Anne Dwane: Chief Business Officer, Chegg

My NativeAdvice:


As Chief Business Officer, Anne is responsible for all of the company's lines of revenue. Anne joined Chegg with the acquisition of Zinch, which enabled millions of students to showcase themselves as "more than test scores" to be matched with colleges, scholarships, grad schools and more. Previously, Anne co-founded to connect service members and veterans to benefits, including GI Bill and career networking. was acquired by Monster Worldwide, where she led affinity networks. Prior, Anne was in business development at Paul Allen's Interval Research Corporation and in brand management for Nabisco. She holds a bachelor's degree in Marketing & International Management from Georgetown University and an MBA from the Harvard Business School. Anne is co-author of Getting In: The Zinch Guide to College Admissions & Financial Aid in the Digital Age (Wiley 2011). She was named a Henry Crown Fellow of the Aspen Institute.

What's Your NativeAdVice:

How did you get into the Tech industry?

Back in the 1990’s, several co-workers at Nabisco identified an opportunity to start a new division within the company leveraging the internet. Since then, I’ve loved the way technology lets you make connections better, faster and cheaper.

Tell us about Chegg. What inspired the idea and what is your vision for the company?

Chegg’s founder, Aayush Phumbhra, was a student on a tight budget. He wondered, “how do you afford college without a great job, and how do you get a great job without college?” It was one of those chicken-or-egg problems, and his solution to that chicken-or-egg problem was an organization he called Chegg. Our mission is to help students save time, save money and get smarter.

Our vision is to be the connected learning platform, matching students with opportunities to learn and succeed from high school through college and into first their job.

What strategic partnerships/marketing strategies have you implemented that have attributed to Chegg's success?

We partnered with Ingram Content Group to improve the Chegg Textbook Rental Service for students. This partnership allows Chegg to focus on the student experience, attractive pricing and selection of books while Ingram provides world-class delivery and logistics. Since Ingram will take ownership of all textbook inventory and warehousing capabilities, Chegg will be a 100% digital company by the end of 2016.

Also, we partner with great brands to “surprise and delight” students with online/mobile discounts and samples in their Chegg textbook delivery boxes.  Students have discovered Tide Pods, new Starbucks coffee items, L’Oréal TREsemmé Shampoo and RedBull products. Students enjoy the unexpected gifts and brands benefit measurably from such targeted, authentic outreach.

Employers are also important partners. 80,000 employers nationwide have posted internships with us to hire students. We acquired to supercharge our career services for students and give employers an efficient way to source amazing talent.

What industry trends are you noticing and how do you capitalize on them?

Learning is increasingly digital, mobile and personalized. This is the “just in time” generation.  Chegg Tutors really fits this trend by providing on-demand experts via voice, video or text.    11,000 tutors (mostly college students themselves) are available for virtually any subject for as low as $0.50 per minute. One-on-one tutoring is really helpful in mastering subjects and getting unstuck; now it’s incredibly convenient and affordable.

Also, while college has never been more essential in the job market, it’s also increasingly expensive. Tuition costs have skyrocketed faster than inflation, student debt has mounted and employment prospects are challenging. College is a good investment, but students and parents want to be savvy consumers. Our college search and match services help students make more informed choices about where to study. We offer students an insider view about life on campus as well as data on graduation and employment rates.  

Finally, internships are a powerful way to build real-world skills and explore different career paths. Companies increasingly value internships in identifying talented future hires. We’re making it easier for students and employers to discover and be discovered.

Life Motto?

Live as if you’ll die tomorrow; learn as if you’ll live forever.

Chegg's Motto?

“Save time, save money, get smarter.” It’s our mission.

Your greatest success as CBO of Chegg?

Hiring people who go on to have a tremendous impact on students, the team and the business.

Most difficult moment-how did you overcome and what did you learn?

Fresh from business school, I arrived for my first day of work at a startup only to find out that my position had been eliminated. On my first day, it was time to look for a new job! This taught me that it’s not what happens to you that matters, it’s how you respond. Resilient, resourceful people succeed. Be grateful for what you have and make the most of whatever hand you’re dealt.

Your advice to an aspiring entrepreneur?

The timing has never been better. Surround yourself with people who make you better, and go!

Describe the ideal experience using Chegg.

A student explores colleges on Chegg to find the right fit. She sees what life is like on different campuses, then views admissions requirements, graduation rates and career outcomes. She’s empowered in the college admissions process by Chegg’s insider tips, essay help, scholarship matches and perspectives from other students. Once she decides where to attend college, Chegg is there to help her succeed and enjoy the experience. We’ll help her save lots of money buying off-to-college essentials including textbooks or eTextbooks.

During the semester, when she’s stuck on an assignment, prepping for a test or mastering a new concept, she’ll turn to Chegg Study and Chegg Tutors for immediate assistance. (She may even decide to become a tutor on the Chegg platform, sharing her expertise as she makes money and builds her resume.)  

Next, she’ll tap Chegg to discover internships that match her major or career ambitions, and land a job as she approaches graduation.   

How do you motivate your employees?

Hire self-motivated people who are inspired by our mission and audacious goals. Work to remove roadblocks so they can achieve meaningful goals and realize their potential.

One food and drink left on earth, what would you choose?

Spicy tacos and a Margarita with a salted rim.  

What literature is on your bed stand?

Gathering Moss, which describes the world of bryology (the study of moss) but is really about observing and appreciating what’s right in front of you. Hidden gems are all around us, awaiting discovery.

Current passion?

Cooking up whatever’s fresh at the Farmer’s Market this week.

Favorite travel destination?

So hard to pick! The south of France. Great food, wine and scenery.

What's next for Chegg?

The back to school “rush,” where we aim to save students money on textbooks and eTextbooks, and introduce them to learning services like Chegg Study or Tutoring to help them save time and master their subjects for higher grades and a more enjoyable term. Standardized test prep services are coming later this Fall. The best is yet to come for students!