Paul Hennessy

A headshot of Paul Hennessy, the CEO of Vroom

It didn’t take Vroom CEO Paul Hennessy long to learn that as a pioneer, you encounter interesting firsts along the way. For instance, when your business is shipping cars to customers’ homes, it’s important to understand the trucks transporting a dozen vehicles often don’t fit down residential streets, let alone driveways.

“We’re delivering something that’s never been done before,” says Hennessy, who joined the company in 2016. Having begun his career selling electronic typewriters at Computerland and then holding executive positions at, Hennessy now merges retail and ecommerce. Vroom sold more than $1 billion in cars in 2016 and ships to all 50 states.

Hennessy says working with talented people on tough problems motivates him daily and has led him to notable technological advances at Vroom. “We’re living in an unbelievable time, where technology is not only enabling but transforming products for customers,” he says. “Data replaces opinions, and key performance indicators replace hunches.” He stresses the importance of experimentation to ensure the right delivery of your product, through the right channels, as defined by customers. If customers want to be able to call on the phone or walk into a store, he says, “You better be able to do that.”