From Teacher to Product Manager

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.

You were picturing this.

As any Teach For America alum will tell you with an eerie level of consistency, teaching is leadership. As a teacher, you have the powerful ability to influence and invest stakeholders to drive measurable results. Have you developed a curriculum map or classroom management system that resulted in more than one year of academic growth during a school year? Congratulations, you are an effective leader with proven results.

The specific competencies related to influencing and motivating stakeholders are foundational to success in not only Product Management, but in any role from Marketing, to Sales, to Customer Success, the list goes on and on.

Resume tip: Less is more. Focus on a few powerful metrics rather than a slew of activities. Assume that a hiring manager will only look at a one-page resume and get ruthless with the available real estate.

Tip #4: Just get in the door.

Many folks often make the assumption that because product managers are individual contributors that the role of Product Manager is an entry level role — it is not.

Product Managers are responsible for developing the strategy that ultimately drives the profit and loss for a business. Thus, a role in product management is a serious leadership role, even if you are not managing people directly. As someone who has the privilege of recruiting, managing, and developing product managers, I recognize that every person I hire is a senior employee and take that work seriously.

When I first considered leaving the classroom, I was initially hesitant to take an entry-level role in ed-tech. After all, I was a leader and senior teacher, why should I be at the bottom of the corporate ladder?

As a wise man [Drake, that man was Drake] once said, “Started from the bottom now we here.” If you are here [principal, lead teacher, coach] the idea of starting from the bottom can feel somewhere between discouraging and demoralizing, I get it.

The truth is, there are very real differences between the day-to-day operations of educational institutions and ed-tech companies. While you certainly understand and empathize with users at a high level, you must also understand the business, market, and technology to succeed in Product.

If you are interested in transitioning from working in education to working in product management in ed-tech, understanding the business is truly essential, and this often means starting with an entry-level role in a department outside of product management.

Don’t be afraid, this is NOT a step backward! As long as you are open to learning new skills and asking questions along the way, you will quickly make up for any perceived loss. And of course, I say this with the caveat that the entry-level role will provide enough compensation to meet your basic needs.

(Mandatory image to warn you that a story is coming)

My first role in ed-tech was in Customer Success, aka entry-level account management. I was paid a teacher’s salary, with the bonus of being able to go to the bathroom whenever I wanted since I was working from home. I began eating lunches that weren’t Lean Cuisines, I adopted a puppy, and I designed and delivered PD too.

This might be a good time to confess that when I first left the classroom, I had never even heard of Product Management.

In that first non-teaching role, I interacted with teachers, administrators, and students in schools across the country. Through those interactions, I began to question aspects of our product’s design and how those design aspects might be impacting our users’ happiness, which would ultimately impact their fidelity of implementation, and our company’s bottom line.

Eventually, I had a manager who escalated those questions to our Product team. One of the product managers actually listened to my feedback and became not only a mentor but a friend. We partnered in research activities, and eventually, the day came when I got my PM wings — I had a chance to turn my research into product changes!

While I had a lot of personal knowledge about educator needs from being a teacher, working as a Customer Success Manager allowed me to develop a broader understanding that I would not have gained otherwise.

Product Management is about solving problems and addressing users’ pain points at a macro level through technology, and there is no way that I would be where I am today without the intermediate step of working in Customer Success. It was through a Customer Success role that I started to ask deeper questions, and asking great questions is at the center of what it means to be a Product person.

As you consider applying to ed tech companies, it is better to spear fish than to cast a wide net. Things to consider, most of which are totally obvious but probably worth stating:

Is there a specific ed tech product that you loved using in your classroom? What did you love about it? What improvements might you suggest?

Is there a specific type of ed tech product or market segment that interests you most? Do you love elementary math or Spanish language arts? Do you have a passion for Student Information Systems?

Does the company’s mission and vision align with your north star? Does their approach to education align with your own theory of change?

When I interview candidates I am not looking for subject matter expertise. I want to understand in specific terms what interested you about this role at our company. If you don’t take the time to dig in and learn about a company before an interview, it’s pretty reasonable to expect that a hiring manager would show that same level of interest in hiring you.

A note on subject matter expertise — if you are a deep subject matter expert in education or pedagogy, a role in Sales Enablement, Professional Development, Instructional Design or Learning Science might be a more satisfying path than Product Management.

Tip #5: Increased compensation does not necessarily equate to increased job satisfaction.

If you are considering leaving the classroom in order to increase your compensation, that’s both common and understandable. I’m sure it’s obvious, but there are many other paths to increasing your compensation in fields outside of ed-tech or product management.

Compensation alone is ultimately not the most important driver of job satisfaction. I suspect that for many teachers, compensation is a factor, but not the top factor, motivating their re-entry to the job market.

New York Times bestselling author Daniel Pink has long asserted that as long as people are compensated at a fair market rate that we are all motivated by three core drivers: mastery, autonomy, and purpose. There’s a whole lot we could say about the teacher compensation issue, but again, this is not that article.

Teachers have purpose in spades. I’m guessing that when you became a teacher, you didn’t do it while quietly saying to yourself, “I can’t wait to spend all of my money at Target.” Educators show up because they are relentlessly committed to their students. Period.

Pink asserts that autonomy is the most important of the three drivers, and I have to say that I agree wholeheartedly. There’s a high probability that I would have never left the classroom if I felt that I had the autonomy to shape school policies as a teacher.

If you are a school or district administrator reading this article, and you are afraid of losing staff to our current climate, I urge you to consider how you might act within your locus of control to expand that of the educators in your scope. How might you create opportunities and hold space for teachers to cultivate mastery and autonomy through high-quality coaching and professional learning?

Conclusion & Next Steps

Here’s our recap —

#1: Commit to continuous learning.

#2: Follow your north star.

#3: [Remember that] You are already a leader.

#4: Just get in the door.

#5: Increased compensation does not necessarily equate to increased job satisfaction.

To say that the last twelve months have challenged educators in an unprecedented way would be a disservice to the incredible work and dedication that school communities have exhibited. Teachers are heroes, they always have been, they always will be.

I am certain that among the lessons of this dark and challenging time will be a renewed appreciation for the selflessness of our educators who continue to show up each day to love each child as if they were their own. And I sincerely hope that this appreciation will turn into systemic policy changes that elevate this profession and compensate educators in a way that reflects our collective reverence and gratitude for their daily work. Again, this is not that article.

Thank you for serving our students in any and every way that you are able. We need your dedication, creativity, passion, and perseverance in this fight because we are in this together, for the long haul.

Teacher turned Product Leader. Obsessed with learning, exploring the outdoors, and my dog.