From Teacher to Product Manager
By: Amber Orenstein
Tags: Education Technology, Career Change, Teaching And Learning, Product Management, Career Advice

Shortly after the beginning of the COVID-19 pandemic I began receiving messages from educators across the country seeking to leave the classroom for a career in ed-tech. More specifically, I have been on the receiving end of this question — How do I transition from the classroom to a career in product management?

In this article, I will seek to answer this question to the best of my ability. Things to keep in mind:

1) Changing careers is a deeply personal decision.

2) I am one person sharing one perspective on a complex topic.

3) This is not a discussion about pathways to promotion in the K-12 education system. That is a very different conversation best saved for another day.

It is an honor and privilege to teach our children. A mentor teacher said that to me on my first day in the classroom, and while it may sound corny or contrived, I wake up every day and quietly remind myself that at the center of my daily work is the trust of a family expecting that I will do everything in my power to help their child succeed.

Twelve years ago, that meant greeting 25 students with a handshake, high five, or hug every morning. Today, that means millions of students will log into the digital products I lead as a Director of Product Management. I cannot stress enough that what I do today is neither more important nor more impactful. It’s. Just. Different.

Those days are gone, at least for now.

As educators, we all remember our first year of teaching vividly and reflect upon that formative year with something between sepia-toned nostalgia and post-traumatic stress. That first year in the classroom teaches each of us invaluable lessons about who we are and arms us with magic tricks we reliably deploy for the rest of our teaching careers.

For me, those magic tricks were largely related to classroom management — coordinating surprise visits from grandma, writing songs to help students commit the order of operations to memory, asking an unruly 7th grader to spit their gum into an outstretched post-it note. If there was a known hack to supporting student achievement, I implemented it daily.

COVID-19 has challenged educators to the core and brought master teachers back to square one. Every teacher is a now, once again, a first-year teacher.

Is it luck or hard work?

At the end of each installment of the How I Built This podcast, host Guy Raz asks game-changing entrepreneurs like Sarah Blakely and Alexis Ohanian to reflect upon the combination or intersection of luck and hard work that propelled their success.

Like those entrepreneurs, I am lucky to lead Product Management for a digital product portfolio that reaches millions of students. My current position is the result of both hard work and luck. I have certainly benefitted from being in the right place at the right time. I’ve had the unique fortune of encountering mentors who took an interest in my professional growth along the way. But I’ve also had to work late nights and weekends to stretch myself as a learner in ways I never even considered while I was in the classroom.

Product careers are not linear and ultimately there are aspects within one’s locus of control (hard work) and outside of that locus of control (opportunities, contacts, timing) that open doors to a career in Product.

Tip #1: Commit to continuous learning.

Product Management lives at the intersection of business, design, and technology. You do not have to be highly technical to succeed, but you do need to have some technical skills.

Read this fantastic newsletter from Gibson Biddle for some expanded insights on how to succeed as a non-technical Product person.

While I was able to secure my first Product role because I spoke fluent “educator” and “7th grader”, I very quickly realized that to succeed in Product I had to become conversational in “businessperson” and “engineer”.

Today, my squad of product managers at Imagine Learning is committed to improving their craft every day. This means that they are voracious readers of thought leadership and continue to develop technical skills such as SQL and advanced user interview techniques. They are open to feedback and coaching, and as a result of their openness to growth and willingness to put in the work they get stronger every day. When hiring a new PM, one of the most important traits I screen for is a candidate’s drive to learn new things. Since this field is always evolving, it’s the lifelong learners who are ultimately the most successful.

Interview Tip: Ask any hiring manager about how they approach professional learning and coaching, including what they are doing to grow themselves. Of course a senior product person should have a high level of mastery, but if they aren’t committed to growing themselves, don’t expect them to invest in your growth either.

For me, professional learning has meant completing a full-stack coding boot camp, earning certifications from the Scrum Alliance, and amassing a not altogether small library of books on design, business, engineering, and human behavior. I take a lot of walks and trips to the dog park with a soundtrack courtesy of Audible.

If you are looking for a reading list, here are some of my favorite resources:

Books: Inspired by Marty Cagan, The Lean Startup by Eric Ries, Sprint by Jake Knapp, Escaping the Build Trap by Melissa Perri, and The Product-Led Organization by Todd Olson.

Thought Leadership: Pragmatic Institute, Product School, Steve Johnson — Under 10 Consulting, and Gibson Biddle.

And, if you are specifically interested in the ed-tech space, be sure to regularly visit Ed Surge and Digital Promise. I am particularly obsessed with the equity-driven design practices outlined in this 2020 publication from the latter.

Tip #2: Follow your north star.

In 2004 as a college freshman at the University of Illinois at Chicago, I registered for an Urban Planning course because it fit my schedule — it changed my life. That course opened my eyes to the deep relationship between public policy, taxation, educational equity, and my own privilege.

As a result of that course and what I learned in it I have spent half of my life dedicated to addressing educational inequity in our country. I am also certain that I will spend the rest of my life committed to making the promise of our democracy, that each child will have access to an excellent education, a reality.

I’ve chased this problem into the classroom and through mostly happenstance meandered into ed-tech — this does not mean that you have to replicate that path. I cannot stress enough how there are other avenues outside of Product Management to make an impact on this issue.

If you are thinking about leaving the classroom, I encourage you to consider the following:

Why did I become a teacher? Is this rationale still relevant to me personally today? Am I fulfilled as a professional? What do I need in order to feel fulfilled by my daily work? What is the problem I want to solve in our society? Is education still the issue I am most passionate about?

Having clear answers to these questions will help inform your next steps and support powerful responses to any questions from a potential hiring manager.

Tip #3: You are already a leader.