Always A Teacher Podcast

How do you translate a rich career as a teacher and administrator into a new role in EdTech, especially when you don't see yourself as a "salesperson"? Where do you find the confidence to take that leap?

In this episode, Matt talks with Marybeth Schultz, School and District Success Manager at Edpuzzle, who shares her inspiring journey from the classroom to a role she defines as a "relationship builder" and "thought partner." Marybeth’s story is a powerful guide for any educator who has felt that "inkling" for a change but is hesitant about leaving the world of education behind.

In this episode, you'll hear:
Why Marybeth reframes her role as "teaching every day" and how this mindset can help educators find an authentic fit in a business environment. 

• Actionable advice on how to build confidence and "practice using your voice" even before you leave your current school. 
• The importance of being patient with yourself, embracing discomfort as a path to growth, and accepting that the journey won't be linear. 
• How to leverage your professional network for support and mentorship to navigate the challenges of a career transition. 

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.

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. 

What does it really take to make a strategic move from the classroom to a rewarding EdTech sales career?

Matt Gambino sits down with Janna Tolleson, a former teacher with 30 years in education who successfully transitioned into a high-achieving sales representative role at Bedford, Freeman & Worth Publishers. Janna shares her honest insights, from the deliberate process of finding the right fit to mastering the art of consultative selling in the education market.

In this episode, you'll learn:

• How to conduct deep introspection and research to discover the EdTech roles that truly align with your strengths and passions.
• Why your classroom "situational acuity" is your ultimate superpower in understanding customer needs and building authentic relationships.
• The critical differences between education and corporate hiring timelines and sales cycles, and how to navigate them patiently.
• How to leverage your natural communication and problem-solving skills to become a trusted advisor, not just a salesperson.

This is a must-listen for any educator considering a career pivot, offering actionable advice on preparing for and excelling in the EdTech industry.

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.

Are you tired of endlessly scrolling through massive job boards, feeling like the right EdTech role is impossible to find? What if you could get a curated list of ideal jobs sent right to you?

Matt sits down with Chelsea Averitt, a former teacher and the founder of Skip, the go-to job board for educators transitioning into the remote workforce. Chelsea provides a candid, behind-the-scenes look at the current EdTech job market and shares the hard-won lessons she learned while building a platform that has helped thousands of teachers "skip" to their next career.

In this episode, you'll learn:

• The truth about the modern job search and why it now takes 3-6 months to land a role in EdTech.
• Why "spraying and praying" with your resume is the single biggest mistake you can make (and how a skills inventory can change everything).
• How to overcome the mental block many teachers have with "sales" and discover roles that are a natural fit for your experience.
• The real reason it's so hard to find quality EdTech jobs and how to navigate the hidden job market.

This is a must-listen for any educator who feels stuck or overwhelmed by the job search and wants a practical, proven strategy for finding their place in the EdTech industry.

In this episode, Matt speaks with former high school languages teacher Ciara Newby, now a Senior Director of Global University Partnerships at Cialfo.

In this episode, Matt speaks with former elementary school teacher Mike Cronley, now Founder and CEO of Class Composer.

In this episode, Matt speaks with former middle- and high-school science teacher Lissa Johnson, now Founder and CEO of Mosa Mack Science.

In this episode, Matt speaks with former middle school math teacher Kiana Porter-Isom, now Chief Improvement Officer with Reading Horizons.

In this episode, Matt speaks with former high school English teacher Cris Slotoroff now Manager of Client Partnerships with The Juice Learning.