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Always A Teacher Podcast

Always A Teacher Podcast

By: Matt Gambino
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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.

© 2025 Always A Teacher Podcast
Career Success Economics
Episodes
  • #030 Courtney Johnson: Account Executive
    Dec 15 2025

    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 work.

    • The Parent-Professional Bridge: Courtney shares the deeply personal story of her own daughter’s speech delay and how witnessing her child’s breakthrough using Age of Learning products solidified her belief in the solution she now represents.
    • The Power of No: We discuss the critical lesson of learning to say "no" without guilt. Courtney explains how establishing boundaries allowed her to protect her peace and, paradoxically, become a more effective leader and advocate.
    • Representation in Special Ed: Courtney dives into the importance of culturally relevant pedagogy and having providers who reflect the demographics of the students they serve, ensuring that "disability" isn't confused with "difference".
    • From Compliance to Community: How growing up in a daycare environment and understanding legal contracts helped Courtney navigate the complex world of Special Education compliance while keeping the focus on family needs.
    • The "Write It Down" Rule: Courtney’s simple but profound advice for any educator sitting on a big idea or a desire for change: Make the vision plain, put it on the fridge, and let it stare you in the face until you act on it.
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    27 mins
  • #029 Susan Casey: Account Executive
    Dec 2 2025

    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 development opened doors she never knew existed.

    • The "Accidental" Educator: Susan shares her unique journey from PTA President and classroom volunteer to a credentialed teacher, proving that it is never too late to step into your calling.
    • Curiosity as a Career Strategy: How Susan leveraged her natural curiosity—attending tech conferences and seeking out new certifications—to build a resume that made her undeniable to edtech companies.
    • From the Classroom to Employee #24: Susan discusses the leap from a structured school schedule to the chaotic, exciting world of an early-stage startup, and how she helped grow Pear Deck from the ground up.
    • Reframing Sales: If the word "sales" makes you cringe, Susan offers a new perspective: it isn't about pushing products; it’s about consulting, problem-solving, and helping districts align their budgets with their goals.
    • Look Local Before You Leap: Susan offers vital advice for teachers looking to leave the classroom but stay in education, suggesting that the perfect intermediate step might be waiting at your local County Office or Education Service Center.
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    27 mins
  • #028 Laura Busch: Customer Success Lead
    Nov 25 2025

    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 these teams.

    • The Player-Coach Model: Laura explains her dual role as a team leader and a hands-on Customer Success Manager, allowing her to mentor staff while maintaining the deep relationships with schools that teachers crave.
    • Defining Customer Success: We break down the difference between technical support and success. It is about ensuring schools get a return on investment and helping teachers find genuine value in their tools.
    • The Empathy Advantage: Business acumen can be learned, but the daily reality of a teacher cannot. Laura discusses how understanding shrinking budgets and teacher exhaustion gives her an instant connection with clients.
    • Navigating Corporate Instability: Laura gets real about the differences between tenure and at-will employment. She shares practical advice on how to research a company’s financial stability before signing an offer.
    • Overcoming Imposter Syndrome: A look at the mental block of feeling like you are just a teacher, and why skills like adaptability and problem-solving are high-value corporate assets.
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    30 mins
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