Always A Teacher Podcast

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 fascinating pivot from the classroom to Digital Learning Coach, and eventually to the role of Chief Technology Officer (CTO) at Springtown ISD . Amanda proves that while technical skills ca...

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 Executive and Entrepreneur, wasn't just about climbing a ladder—it was about expanding her sphere of impact. In this episode, Courtney shares how she leverages her deep expertise in Special Educa...

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 becoming a credentialed teacher later in life, Susan has always followed her curiosity. Today, she is an Account Executive for Pear Deck Learning, where she continues to impact education on a massive sc...

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, Laura shares how she went from Instructional Technology Coach to Regional Customer Success Lead at Linewize, a global provider of student digital safety solutions. Laura pulls back the curtain on what C...

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 career where she now impacts thousands of classrooms instead of just one. In this episode, Jess opens up about the emotional reality of transitioning out of Early Childhood Education (ECE) and how she land...

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 episode, Maggie shares her story of transitioning into EdTech, starting with an entry-level sales support role and leveraging her teacher's mindset of "nurturing" and "empathy" to...

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 her current role at YouScience , a gamified career assessment platform that helps students discover their natural aptitudes. She offers powerful insights on aligning your career with your personal missi...

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 find a new path that realigns with what drives you? In this episode, Matt talks with Laura Litton , Director of Success at LiveSchool . Laura shares her powerful journey from instructional coach to school...

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 talks with Caelan Boone , a former secondary math and science teacher who is now a Customer Success Associate at Swing Education , an online marketplace connecting schools with substitute teachers. Cael...

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 episode, Matt talks with David Thomas , National Vice President of Strategic Partnerships at RethinkEd . David shares his remarkable journey through multiple facets of the education world—from his time...

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...

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 mid...

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...

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...

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 a...

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 .

In this episode, Matt speaks with former English teacher Donna McConnell, now an Account Executive with 95 Percent Group .

In this episode, Matt speaks with former art teacher Christine Hayes, now the Senior Director of Customer Success and Sales Enablement with Zūm .

In this episode, Matt speaks with former middle school social studies teacher Steve Guerriero, now the Chief Learning Officer with Litmus Learn .

In this episode, Matt speaks with former high school English teacher Gerard Dawson, now a Product Manager with Swivl.

In this episode, Matt speaks with former high school teacher Emily Peddle, now a Director of Professional Learning Programs and Partnerships with Southern New Hampshire University.