#20 Tyler Post: Account Executive

What happens when you achieve a leadership position in education, like a school principal, only to find that the path forward isn’t sustainable for you? How do you pivot from a role at the heart of a school building to a new career in the EdTech industry?

On this episode of Always A Teacher, Matt sits down with Tyler Post, who made that exact transition. Tyler shares his journey from teaching middle school social studies to becoming a Dean of Students and Principal, and ultimately, to his current role as a successful Account Executive at CrowdComfort, a real estate technology company serving K-12 and higher education.

In this episode, you'll hear:

• The candid reasons why even successful school administrators consider leaving the profession, from the emotional toll of the role to the need for better work-life balance.
• Tyler’s deliberate, year-long strategy for making the career change, including the crucial role of a career coach, deep self-reflection, and networking.
• How core teaching skills—like distilling complex topics and being aware of different learning styles—are directly transferable to effective sales conversations.
• The surprising shift in how he leverages his background—moving away from leading with his title to letting his deep understanding of school operations build credibility organically.

The Always A Teacher podcast is for educators who are considering a transition from the classroom to the EdTech industry. Host Matt Gambino, founder of Propel Skills, the number one sales training firm serving EDU and EdTech businesses exclusively, taps into his network to bring you the stories, secrets, and skills you need to make the move.

 Learn more about sales training for your EdTech team at propelskills.com. 

Thinking about transitioning? Explore your path with our EdTech Transition Checklist to get started!