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.

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

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!

In this episode, Matt speaks with former 7th-grade teacher and higher ed instructor Chelsea Avirett, now the founder of Skip.

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