
Always A Teacher Podcast
What happens when you decide to leave teaching and pursue the next chapter in your career? The Always A Teacher podcast provides teachers with insights and advice for breaking into the EdTech space. Hosted by Matt Gambino, the nation's top trainer of EdTech industry professionals, Always a Teacher features wide-ranging interviews with former teachers and administrators who share their stories about transitioning from the classroom to EdTech, and how they apply their unique skills and passion for students to a business setting.
Always A Teacher Podcast
#018 Jonathan Strout: Enterprise Account Executive
What does it really take to go from the principal's office to a top-tier role in an EdTech company?
Matt Gambino sits down with Jonathan Strout, a former high school principal who successfully transitioned into an Enterprise Account Executive role at Renaissance Learning. Jonathan shares an unfiltered look at his journey, from the personal "inflection point" that led him to leave a 24-year career to the nitty-gritty of succeeding in the corporate world.
In this episode, you'll learn:
- The single biggest mindset shift required when moving from a reactive school environment to a proactive sales role.
- Why leading with your "former educator" status can be a cringe-worthy mistake.
- How to leverage your deep knowledge of schools to become a trusted advisor, not just another salesperson.
This is a must-listen for any teacher or administrator looking for honest, actionable advice on breaking into the EdTech industry.
Thinking about transitioning? Explore your path with our EdTech Transition Checklist to get started!