The leap from school administration to the world of EdTech sales can feel daunting. The skills that make a great principal—managing staff, supporting students, and putting out daily fires—don’t always seem to translate directly to a sales quota. But what if that perspective is the key to success?
In a recent episode of the Always A Teacher podcast, I spoke with Tyler Post, a former middle school principal who successfully navigated this transition to become an Account Executive at CrowdComfort. His journey from managing a school building to solving operational challenges for K-12 districts offers a powerful playbook for any educator considering a similar move. He proves that the most valuable asset you bring from your education career isn't your title—it's your deep understanding of the problems schools need to solve.
Laying the Groundwork: The Power of a Deliberate Transition
One of the most common fears for transitioning educators is the feeling of starting over. Tyler’s story counters this fear with a lesson in intentionality. Instead of rushing into the first available role, he approached his career change with the same thoughtfulness he would a new school year. He invested time in a structured process of self-discovery to ensure his next step was the right one. This deliberate approach, while it took time, built a foundation for long-term success.
"What I did is, is actually, I decided to work with a career coach. And for me, it was an excellent decision. It was a long process... there was a year, really, of laying the groundwork, a lot of introspection... a lot of... journaling and really thinking through what are the skills that I've developed, you know, what experiences have I enjoyed? You know, what could that potentially line up with?"
From Lesson Plans to Sales Plans: Translating a Teacher’s Toolkit
A veteran educator's greatest strength is their ability to make complex information understandable and relevant. Tyler found that this core teaching skill was not just helpful in EdTech sales—it was essential. When introducing a new technology solution to a district, he draws on his experience as a teacher, anticipating assumptions and breaking down concepts into digestible parts. This ability to educate the customer, not just pitch to them, is a powerful differentiator that builds trust and clarity.
"When you're teaching, you're always reminding yourself, you've got these kids in front of you... and it's really easy to make all these assumptions... about what they might be understanding... So I think, you know, trying to sort of distill concepts down, and keep them in understandable chunks, being aware of different learning styles and that this is something that people haven't seen before."
Beyond the Title: Earning Credibility by Solving Problems
Many transitioning educators believe their former title is their primary source of credibility. While it can open doors, Tyler learned that true trust is built by focusing on the customer’s reality, not your own resume. He shared a crucial evolution in his approach: he stopped leading with the fact that he was a principal and started focusing exclusively on identifying and solving his prospect’s problems. His background gives him the empathy to understand those problems deeply, but his credibility comes from his ability to offer a viable solution.
"It's funny, I used to bring it up almost right away, you know, because maybe it gives me a certain level of credibility... and then, you know, sometimes I don't bring it up at all honestly, anymore... I think it's more about the experience I've had and what I know about schools... Ultimately, it's selling. It's like you're identifying a problem somebody has and determining how you can support them with that problem."
Listen to the Full Conversation
Tyler’s journey is a masterclass in how to thoughtfully pivot from a career in school administration to a successful role in EdTech. His insights on preparation, skill translation, and building authentic credibility are invaluable for any educator looking to make a change.
Listen to our full conversation on the Always A Teacher podcast to hear more.
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