“Winning Is a Decision”: Paper CEO Philip Cutler Is Changing Online Learning

When Covid first hit, the CEO of ed-tech start-up Paper made a bet on virtual learning—and it paid off big time
Paper CEO Philip Cutler

In his early career as an elementary school teacher, Philip Cutler noticed a disparity among his students when it came to their ability to access tutoring. The students who were getting extra support were typically the wealthiest 20 per cent—but they were rarely the ones who most needed the help. So, in 2015, Cutler co-founded Paper, an ed-tech service used by schools in North America to provide accessible virtual tutoring to more than 2.5 million students. This summer, the company secured $343 million in Series D capital, bringing its total funding to $496 million.

Age: 33
Based in: Montreal
Degree: B.A. in education (McGill University)

I thought I’d grow up to be:

An athlete. I always enjoyed playing hockey, football and golf, but then I realized I don’t have to be a professional to play sports.

The best advice I’ve ever heard:

If you can actually solve a problem with money, then by all means, solve it with money. However, most problems in business and life can’t be solved with money alone.

My most memorable mistake:

My mistakes have pertained to people—either not investing enough in those who showed promise early on or counting on people because of their experience, even if they didn’t necessarily have the conviction or drive. I will no longer let a hiring manager so easily convince me of a candidate by saying “Hey, this person’s great. Look at their experience.” I have to trust my instincts regardless of what the resumé says.

The hardest decision I’ve had to make:

When Covid first hit in 2020, there was turmoil everywhere. The advice I heard was: “This is a time to slow everything down. We don’t know where the world is headed.” When everybody else was telling me to do the opposite, I made the tough decision to invest heavily in a big transition to virtual learning and tech adoption in schools. I thought that if we could navigate through this successfully, we’d build a big business and support a lot of students as a result. Everything ended up working out.

I never confuse:

Activity with productivity. We live and breathe by the difference between doing something and actually making a difference.

The words I most overuse:

“Winning is a decision.” It’s basically our philosophy at Paper. In our case, we define winning as supporting students better.

This article appears in print in the fall 2022 issue of Canadian Business magazine. Buy the issue for $7.99 or better yet, subscribe to the quarterly print magazine for just $20.

Adrienne Matei
Adrienne Matei
Adrienne Matei is a freelance journalist based in Vancouver, Canada. She writes about culture, technology, lifestyle, the environment, and more.