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

Philip Cutler is the CEO of Paper Education, a company that improves educational equity by delivering individualized support to students who need the most help. We discuss his path from teacher to founder, how he leads a mission-first organization, and how some teachers set themselves apart by bringing positive energy to the interview process.

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.

On the first day of school in the big auditorium, they handed us a sheet of paper with a pay scale on it and said, “this is exactly how much you will make every year as a public school teacher.” When I realized my whole professional career would be summed up on that 9x11 piece of paper, I wasn’t sure teaching was for me. I loved the program and the people, though, so I decided to give it a shot.

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.

I ended up starting my own home tutoring business to earn money and meet the requirements of the program, and it was pretty successful. The whole time, though, I was only serving the wealthy families. When I started teaching, I realized that the students who were most successful were the ones who could afford that extra help. The other 90% needed the help the most but didn’t have the resources at home…and no one was serving that side of the market.

I left teaching early on to start Paper with my cofounder and work toward educational equity. It has grown beyond what I ever imagined when I initially left teaching, but the goal was always the same.

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.

It helps me get through the challenging times as a founder, too. The number one reason startups fail is because there are issues between the founders; they end up quitting the business or the mission. The truth is that if you’re building a billion dollar company and you want to change the world, there has to be a lot more to it than just the number crunching. You really have to be passionate about what you’re doing.

7 years into Paper, it has absolutely been a rocky road… but if I’m having a rough day or week, I just watch students come onto the platform and remember that we’re helping kids. It reminds me that this isn’t just a company that needs to deliver returns to shareholders. I can always put the mission ahead of everything else I have to do.

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.

One skill really helped me when I started Paper was reflection. I knew very little about business, let alone startups and venture capital, but I knew how to reflect productively on my experiences. My teaching program had emphasized this, and I was also on the football team where I spent tons of time watching film. So after every meeting, I would write down notes and spend lots of time rereading them. I watched founders pitch, watched CEOs giving reports, and even recorded and rewatched myself during my own meetings. This could be painful, but I was used to it. That set me apart from a lot of founders early on.

The other thing that was quite transferable was my comfort around people. I’m introverted by nature, but teaching forced me to learn how to command a situation. If you don’t have authority, it’s a mess. When I was able to pitch and run the business, that extroverted presence was there even though it wasn’t natural to me. Every good teacher can relate to that — it’s something that you can inject into any new pitch as a founder. Presence is key.

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.

On the other hand, you have the candidate who comes in and is like “I’m a great teacher, I can take those skills and talents and bring them to your company.” At Paper, we have teachers in every role: one of our top Sales representatives is a teacher, even one of our engineers. Every single one of them has been really gung ho during the interview process: they’re still motivated by education and not turned off by it. When they come in with an enthusiastic attitude and project confidence in their skills, that’s a huge advantage.

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.

As an organization that’s growing quickly and dealing with challenges, the last thing you need is negativity or egos. Those things are toxic. You need people who are positive and problem solvers, and tons of teachers have those qualities.

If you feel anything like I did a few years ago, that last point might be easier said than done. After all, it’s hard to stay upbeat during an emotionally draining job hunt (while working in an even more emotionally draining job). When you’re writing a cover letter or talking to a hiring manager, how can you convey enthusiasm while remaining authentic about your reasons for pursuing a change?

Well, you’re in luck — I’ve created this guide to being honest-but-not-too-honest about your decision to leave the classroom!

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

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Transitioning Teacher

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