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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.
31 Episodes
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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 can be learned, the leadership and management skills forged in the classroom are the true drivers of district s...
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 Education and her personal experience as a mother to champion literacy and numeracy tools that actually wor...
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 scale. In this episode, Susan shares how staying curious and saying "yes" to professional developme...
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 Customer Success really means in edtech and why former educators are uniquely qualified to lead th...
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 landed a dream role at Frog Street, a company that perfectly aligns with her passion for little learn...
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 build a successful corporate career. A Family of Teachers: Maggie shares her deep roots in education, coming from a family...
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 mission and provides grounded advice for any educator considering a similar leap. Key Takeaways from the...
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 principal and, ultimately, to a fulfilling career in EdTech where she rediscovered her love for co...
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. Caelan shares her journey from the classroom to the corporate world, detailing the steps she took to su...
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 as an instructor and administrator in higher ed to his work in K-12 and his current executive role...
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 ...
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 cur...
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 l...
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 sing...
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 platfo...
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.
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