FREE ON-DEMAND SESSION

From classes to customers: Unlock your sales career in edtech

In this session, we demystify the world of edtech sales and show you how to leverage your unique teaching experience to land a rewarding, high-impact role.

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100% free. No spam, ever.

Stop "just applying" and start building your path.

If you feel stuck, underpaid, or that your skills aren't valued outside the classroom, this session is for you.

In this free session, you'll learn how to:

See yourself in sales: Understand the current edtech sales job market and why your educator skills are more relevant than ever.
Identify your superpowers: Pinpoint the transferable skills you already possess—like situational acuity, time management, and crisis management—that will make you a successful sales professional.
Target the right roles: Discover "low-hanging fruit" positions like Learning Technology Consultant, Education Specialist, and Curriculum Specialist that are a natural fit for transitioning teachers.
Analyze and qualify: Learn to dissect job descriptions to determine if a role is the right fit for you and how to qualify yourself as a top candidate.
Pitch with confidence: Master the art of pitching yourself, from crafting a compelling narrative to nailing the interview and winning the job.

This framework works. See for yourself.

"The week after Matt's training, I put his lessons into practice and it worked like a charm! As a former educator, I was so thankful for the ample practice and role-playing we did. It truly prepared me for the different avenues my conversations with customers could take. He’s also hilarious, so the whole day felt like fun!"

Natalie Kass

Former Middle School English Teacher

"As an educator, I know what a good presentation looks like, and Matt is one of those presenters who makes you want to pay attention. He breaks things down in a way that’s so relatable and easy to grasp. His style is informative without ever feeling like a lecture—you’re learning the whole time, but it’s so engaging you hardly notice."

Janna Tolleson, M.Ed.

Former Assistant Principal

"As a 20-year education veteran, I can confirm the effectiveness of Matt's approach from all sides. He delivered a session for our team that was engaging, informative, and highly effective. I can't speak highly enough about the content and his process."

Rick del Rosario

Former Director of University Admissions

Meet your guides

Matt Gambino

I’m Matt Gambino. My entire 25-year-career has been spent in two worlds: education and edtech sales.

I’ve been a salesperson, a sales leader, and a consultant, but the most talented, empathetic, and effective people I’ve ever worked with are all former teachers.

My podcast, 'Always a Teacher,' and my training are built on one simple truth: the skills you mastered in the classroom are exactly the skills you need to be a successful, trusted advisor in edtech.

Chelsea Avirett

Chelsea Maude Avirett is a former educator and the founder of Skip (edskip.com), the leading job board for educators transitioning into new careers.

After experiencing the frustration of the job search herself, she built Skip to connect teachers with opportunities that value their experience.

She has personally curated over 10,000 jobs, has nearly a decade of experience interviewing candidates, and is a sought-after speaker on edtech hiring trends.

Start your journey from the classroom to a career you love.

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