Q&A with Philip Cutler, Teacher-turned-EdTech-CEO

What drew you to education?

I was one of those students who didn’t have a master plan. My parents were the “do what makes you happy” type; no one was pushing me in any direction when I went to college. I knew I liked school as a student and was motivated by working with kids, so I thought maybe I could be a teacher. In the back of my mind, I knew I was entrepreneurial, so I didn’t know if I’d work in education forever but I saw it as a great starting point. I went to McGill’s elementary education program. I saw classroom teaching as one option for me to pursue with that degree and not the only option, but I felt like the program kept pushing us in that direction.

What eventually motivated you to start Paper?

During our first year in school, our professors told us we needed teaching experience right away, but since we weren’t credentialed as teachers we would have to find a way to tutor. I looked around at my class and realized we were all facing the same problem, so I started putting ads on Craigslist to look for students.

That resonates with me — it has been helpful to realize there are so many ways to improve equity in education beyond being a classroom teacher.

Yeah, it motivates me! And it motivates our whole team. Just because you’re in Sales or Marketing or Engineering… that may be your skillset, but that’s not why you want to work at Paper. You want to work with us because you believe in what we’re doing, and you want to use your skills to benefit students.

Did your background in education help you as an entrepreneur?

I felt like a lot of what I learned in my four-year teaching program was not applicable to teaching OR to business. Most is learned on the job: your first day in the classroom is when you start figuring it out. You have the theory, but the practice is very different. The same thing is true in business.

You’ve hired many former teachers throughout your career. What do the best candidates do right, either in the resume stage or during the interview process? What mistakes do teachers commonly make when applying for jobs outside of the classroom?

I’ll start with where I think they fumble. A lot of the time, we’ll get applicants who come from teaching and feel jaded by the profession. They see a company like Paper as their freedom, and they’ll say that to you quite candidly. There may be merits to that; after all, I’m an example of someone who didn’t cut it as a teacher! Still, you can tell that the person has been defeated by education and doesn’t know what to do next.

That’s absolutely critical, and I get why it can be hard. Teachers who are leaving the classroom because they feel frustrated or tired might bring a sense of defeat into the interview process, even unconsciously.

Probably. I’ve seen back-to-back interviews where one teacher is positive and one teacher is negative. I always ask myself if I left the interview feeling more energized than when I came in. If the answer is yes, you’ll get to the top of the stack.



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Transitioning Teacher

Transitioning Teacher


I help teachers transition into meaningful careers outside of the classroom!