Okay, so the official title of this episode is “From The Principal’s Office to EdTech AE: How Jonathan Strout Redefined His Value,” and I have to admit, that doesn’t exactly roll off the tongue. We’ll work on it.
Regardless, I recently sat down with Jonathan Strout, a former high school principal who made the courageous leap into the EdTech industry and is now a successful Enterprise Account Executive at Renaissance Learning. I was thrilled to have him on the show because his perspective was a bit different than some of the other former educators I’ve interviewed.
This conversation is a must-listen for any school administrator or teacher weighing a similar path. Jonathan was refreshingly honest about the realities of the transition—from confronting burnout and “the guilt of leaving” to the surprising ways his educator skills translated (and didn’t) to the corporate world.
The Real “Why”: More Than Just a Career Change
While Jonathan loved his 24-year career in education, he reached an inflection point familiar to many school leaders. The role was a “nonstop 24/7, 365 job,” and the stress, amplified by the pandemic, was taking a toll. The decision to leave wasn’t just about a new job; it was about reclaiming his life.
“I got to an inflection point in my life where… I was saying how much more of my own kids’ lives am I going to miss? How much more stress am I going to be willing to endure? Do I have the transferable skills to be able to make this leap?”For Jonathan, the goal wasn’t just work-life balance, but work-life flexibility—the ability to be present for his three children and have more control over his schedule.
The Biggest Challenge: From Problem-Solver to Problem-Finder
One of the most profound shifts Jonathan experienced was in his daily workflow. As a principal, his world was reactive, fielding 250-300 emails a day and constantly solving problems that came over the transom. In EdTech sales, that dynamic completely flips.
“My email—I wish I got 250 to 300 emails a day! That was probably the biggest shift… going from constantly reacting to everyone’s issues or problems or challenges to going out to find them. I had to shift from being a problem-solver to a problem-finder.“
This is a crucial insight for any educator considering a sales role. The job isn’t about waiting for issues to arise; it’s about proactively seeking out challenges in the market and identifying where you can provide a solution.
How to Use Your Educator Credibility (Hint: It’s Not How You Think)
Perhaps the most valuable lesson from our conversation was Jonathan’s sophisticated take on “educator credibility.” Many former teachers believe leading with their past title is their biggest advantage. Jonathan admits he made the same mistake early on.
“I cringe sometimes when I think about my first year in sales and some of my first conversations and demos where I always led with… what my roles were and my titles are. It rarely comes up where I tell them what I did, unless they ask.”
He discovered that real trust isn’t built by giving the former-teacher secret handshake. It’s built by using his deep experience to genuinely understand a customer’s pain points. His background allows him to accelerate conversations, get to the root of a problem, and act as a true, authentic consultative partner—even if it means recommending a competitor’s product.
Jonathan’s Top Advice for Making the Leap
For those considering a similar transition, Jonathan offers three pieces of advice:
- Do Some Soul-Searching: Are you leaving because of a single recent incident, or a long-term feeling of overwhelm coupled with a belief you can succeed elsewhere? Get clear on your motivation.
- Become a Student: Once you identify a potential path (sales, customer success, etc.), consume everything you can. Learn the language, the challenges, and the key players so you can speak confidently when the opportunity arises.
- Be Unapologetically Assertive: Go after what you want with focus and determination.
This episode is packed with honest reflections and actionable advice for educators exploring what’s next.
Find Jonathan Strout on LinkedIn.
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