Episodes 31
Avg. Duration 35m
Activity Declining
Since Apr 2023
Latest Episode Jan 2026

Publishing Details

Schedule
Every 2 Weeks
Format
Episodic
Consistency
27%
Hosting
rss.buzzsprout.com

About This 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.

Podcasting 2.0 Features

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Recent Episodes

S4E31 #031 Amanda Lanicek: Chief Technology Officer

Jan 25, 2026 38m

Is it possible to lead a district’s technology department without a background in networking or computer science?For Amanda Lanicek, the answer is a resounding "yes." In this episode, we explore her…

S3E30 #030 Courtney Johnson: Account Executive

Dec 15, 2025 27m

Can setting boundaries actually make you a better advocate for your students?For Courtney Johnson, the journey from Special Education teacher to District Administrator, and finally to edtech Account…

S3E29 #029 Susan Casey: Account Executive

Dec 02, 2025 26m

Is your curiosity the key to your next career chapter?For Susan Casey, the path to the classroom—and eventually out of it—was anything but traditional. Starting as a dedicated PTA volunteer before…

S3E28 #028 Laura Busch: Customer Success Lead

Nov 25, 2025 30m

Do you feel like your skills are limited to the walls of your classroom?For Laura Busch, transitioning from an 18-year teaching career to the corporate world was a strategic move. In this episode,…

S3E27 #027 Jess Hammond: Senior Director of Learning and Development

Nov 19, 2025 22m

Is the teacher guilt of leaving the classroom holding you back from your next chapter? For Jess Hammond, the decision to leave her Pre-K students was heart-wrenching, but it opened the door to a…

S3E26 #026 Maggie Fiorentino: Vice President of Product Marketing

Nov 03, 2025 28m

What does the journey from a Pre-K classroom to a Vice President of Product Marketing look like? For Maggie Fiorentino, it was a path defined by the core skills she built as an educator. In this…

S3E25 #025 Ivey Harrison: Senior Territory Manager

Oct 16, 2025 36m

In this episode, Matt speaks with Ivey Harrison, a former college administrator who successfully transitioned into the EdTech industry. Ivey shares her inspiring journey from college counseling to…

S3E24 #024 Laura Litton: Director of Success

Oct 09, 2025 37m

What happens when you reach a leadership role in education, only to find that the day-to-day work has pulled you away from your true passion? How do you pivot from a role like school principal to…

S3E23 #023 Caelan Boone: Customer Success Associate

Oct 03, 2025 21m

How do you turn a passion for teaching into a thriving career in EdTech? And what are the real, tangible skills that companies are looking for when they hire former educators?In this episode, Matt…

S3E22 #022 David Thomas: National Vice President of Strategic Partnerships

Sep 22, 2025 33m

Do EdTech companies really value classroom experience? How does a career dedicated to serving students in K-12 and higher education translate to a leadership role in a corporate environment?In this…

S3E21 #021 Marybeth Schultz: School Partnerships Manager

Sep 15, 2025 30m

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…

S2E20 #020 Tyler Post: Account Executive

Sep 04, 2025 41m

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…

S2E19 #019 Janna Tolleson: High School Sales Rep

Jun 24, 2025 43m

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…

S2E18 #018 Jonathan Strout: Enterprise Account Executive

Jun 07, 2025 31m

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…

S2E17 #017 Chelsea Avirett: Founder

May 28, 2025 48m

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…

S2E16 #016 Ciara Newby: Senior Director of Global University Partnerships

Nov 17, 2024 33m

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

S2E15 #015 Mike Cronley: Founder & CEO

Nov 08, 2024 35m

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

S2E14 #014 Lissa Johnson: Founder & CEO

Nov 04, 2024 29m

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

S2E13 #013 Kiana Porter-Isom: Chief Improvement Officer

Oct 22, 2024 39m

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

S2E12 #012 Cris Slotoroff: Manager of Client Partnerships

Oct 03, 2024 33m

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

Frequently Asked Questions

How many episodes does Always A Teacher Podcast have?

Always A Teacher Podcast has published 31 episodes since April 2023, covering topics in Business, Careers.

Is Always A Teacher Podcast still active?

Always A Teacher Podcast is currently declining with new episodes every 2 weeks. Average episode length is 35m.

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