The former CEO of Chegg Inc. and current member of the Martha and Spencer Love School of Business Board of Advisors returned to campus for the Lessons from Leaders series to talk directly with students about building a purposeful career.
Lessons from Leaders welcomed Nathan Schultz ’00, former CEO of Chegg Inc. and a current member of the Martha and Spencer Love School of Business Board of Advisors, to the LaRose Digital Theatre on Oct. 29 for a conversation on risk, AI and building a career that reflects your values.
“I did not show up here feeling like I fit in,” said Schultz of arriving at Elon from Topsfield, Massachusetts. “What changed everything was the community. The faculty here actually cared. They let this scruffy kid with dreadlocks figure it out.”
Growing up with dyslexia and ADHD shaped how he sees learning and leadership.
“I will never underestimate the power of clear writing,” he said. “Your ability to explain what you are doing and why it matters is the glue in corporate America.”
Schultz traced his path from history major to leading an education technology company through a series of intentional risks.
“We had textbooks in a supply closet. It was risky. But I believed we could make education more affordable and fair.”
That idea led to one of his central messages for Elon students.
“I have always had a ‘say yes’ philosophy,” Schultz said. “You are not going to have every step mapped out. Say yes, then do the work to figure it out.”
Students asked Schultz about Chegg’s evolution as a company, artificial intelligence and academic integrity.
“We had been using machine learning for years,” he said. “What nobody predicted was how fast AI would reach consumers. The question is not ‘AI or no AI.’ It is ‘Are you actually helping students learn, or are you taking shortcuts?’ If we get it wrong, you stop trusting the brand. We do not get to be casual about that.”
On culture and decision making, Schultz was equally direct.
“Debate the ideas hard,” Schultz said. “Decide. Then walk out of the room on the same page. You do not get to leave the meeting and say, ‘I think this decision is stupid.’ That destroys trust.”
He was candid with students about layoffs, strategy shifts and the role of AI in the workforce.
“Will AI replace some work? Yes,” he said. “But the real story is about shifting to higher-order problems. The people who will thrive are the ones who can think, write, adapt and use these tools well.”
His parting advice to students facing graduation pressure?
“At 22, I wanted everything figured out,” Schultz said. “Looking back, I would tell myself, ‘chill out.’ You have 50 years to work. You do not need the perfect plan. You need curiosity, integrity and a willingness to keep learning.”
About Lessons from Leaders
Launched in 2017 by Dean Emeritus Raghu Tadepalli, Lessons from Leaders brings senior executives to campus for open talks, small-group roundtables, and purposeful one-on-one networking that connects students with mentors. The program bridges classroom learning with real-world decision-making and aims for every student to leave with a new contact and an actionable career insight.