Five Tips for Making the Leap from Teaching to Edtech

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I took the plunge. After five years in schools as a teacher and technology integrator, as well as being a part-time consultant at a startup, I am proud to be joining TeachBoost full time this summer.

Throughout this process, colleagues at my school, at conferences, and on social media have asked for my advice as they have considered switching from schools to edtech as well. Now that I’ve finished the transition, here are a few tidbits that I learned over the past year.

1. Consult first

One of the best decisions I made was to join Ponder as their academic liaison, which allowed me to work full-time last summer and part-time during the school year. I’ve written at length about the value of this position to startups, but it’s great for teachers, too. I saw firsthand what a well-run, promising, mission-driven company looks like. The excitement and challenge of working for a startup became clear. I learned exactly what the day-to-day life is like at a startup, and whether that was the life for me. The academic liaison role also proved to potential employers that I knew what I would be getting myself into.

2. Be 100% sure you’re ready to leave schools

Once you’ve put a toe in the startup waters, you’ll know how ready you are to dive in. It’s not easy. Teaching is a relatively secure job. Startup work, by its very nature, isn’t. Moreover, working for a startup is fulfilling and rewarding, but in a much different way than teaching.

At TeachBoost, I hope to help thousands of administrators improve their teacher effectiveness, which will ultimately benefit students. But at the same time, I’m also giving up the joys unique to teaching: inspiring a love for reading and writing, for engineering, for leadership; helping kids become better people; and more. Are you sure you’re ready to do the same?

One way to know is to move into a professional development role first. When I became a technology integrator, I worked primarily with teachers. I missed my kids and my classroom, but I enjoyed helping other teachers find ways to inspire students using technology. This experience made the transition into edtech--one more step away from the kids—less jarring.

3. Be scrappy in your search for openings

EdSurge’s job board and AngelList are invaluable. Get the free month of “Job Seeker Premium” on LinkedIn and make good use of InMail. “Cold call” emails are a great tool for finding openings that aren’t public and for soliciting referrals to other openings. If you identify companies that interest you, send a note asking to learn more about the company, and suggest that you’re conducting a job search. Even if they have no openings now, you’ll make some great new connections for the future. Maybe the founder of the company you love isn’t hiring, but he has a friend at another company who is. In fact, network as much as you can. Go to meetups, chat with well-connected people on Twitter, and ask for help. No one got to where they are on their own, and everyone loves an opportunity to pay it forward.

4. Learn how to sell yourself

Teachers add tremendous value to edtech companies. Once you identify a new opportunity, prepare your application strategy. EDpuzzle founder Quim Sabria, who I was fortunate enough to meet while networking over these past few months, explained his thinking in hiring teachers:

Every worker in EDpuzzle has ‘teacher DNA.’ Our parents are teachers or we have been teachers before. We have lived the challenges and needs in the classroom. Because it is in our DNA, we believe in our job and we work hard (really hard) to achieve our goals, no matter what.

Skills and knowledge can be learned, but the DNA is something really hard to change. For this reason, when we hire a new EDpuzzler, we make sure that their DNA will match with ours. If they have this bond with the project and have the skills to take EDpuzzle to the next level, we will empower them to have a real impact.

Edtech companies understand the value of your background. You’ve already demonstrated that you’re passionate about education; play that up as much you can, while convincing the company that you’re passionate about their mission and the role you might play in fulfilling it.

To be persuasive, you have to be genuine and well-informed. When you find openings, learn as much as possible about companies before you apply. What’s the company’s mission? How quickly have they grown? Are they funded? By whom? What’s their culture like? What sort of backgrounds do their current employees have? Startup employees are extremely passionate about what they do, just like teachers are. It’s risky to bring on another person, so they want to know that you’re as committed to the company as they are. If you don’t share their values or agree with their mission, then you shouldn’t apply.

Next, move from the macro to the micro and learn about the roles you could fill in the company. Sales, marketing, and product development are pretty unfamiliar to most teachers. Read The New Strategic Selling, Guerilla Marketing, and Inspired: How to Create Products Customers Love. Learn to talk the talk. You don’t need to be an expert, but you want to be able to identify what your strengths and weaknesses are. My new colleagues are eager to support me, but I also know what questions to ask. Just like a first-year teacher, you’ll get a lot of on-the-job training, but some targeted professional development goes a long way.

5) Be selective

Edtech is booming. It seems like every time Pearson or Houghton-Mifflin acquire a company, another three pop up.

Not all edtech companies are created equal, though. And it's essential that you hedge the risk of joining a startup by confirming that the company's mission and its leaders are on the same page as you.

Don’t be afraid to ask tough questions that you couldn't glean from Internet research in preparation for your interview. Ask how meetings with investors have gone and who is and has been interested. Ask the founders where they see the company in five years, ten years, twenty. Ask what their definition of success is. Ask where you’ll fall on the company organization chart. Trustworthy companies will be open and direct with their answers, and they’ll completely understand your prudence. In fact, they’ll appreciate it.

The switch from schools to an edtech startup was a stressful, exciting, and scary process, like any career move. I’m thrilled to have landed at a company with such enormous promise that also affords me an opportunity to grow. While I miss my students and colleagues, I am also certain I made the right decision.

If you’re considering launching a similar search, start now by putting in hours for another startup this summer. And in the spirit of paying it forward, feel free to reach out to me on Twitter so we can set up a time to chat.

Good luck!

Ben Stern (benstern0) is an Account Executive for Dropbox for Education.

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