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Always A Teacher Podcast

Always A Teacher Podcast

Written 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.

© 2026 Always A Teacher Podcast
Careers Economics Personal Success
Episodes
  • #031 Amanda Lanicek: Chief Technology Officer
    Jan 25 2026

    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 success.

    • The Unlikely CTO: Amanda shares her journey of stepping into a highly technical leadership role by leaning on her instructional background and trusting her ability to learn the "nuts and bolts" along the way.
    • Teachers as Managers: We discuss why society overlooks the management prowess of educators. Amanda argues that if you can manage 22 students and a curriculum, you have the foundational skills for executive administration.
    • The "Alligator" Email: Amanda offers a valuable lesson for sales professionals on how to cut through the noise. (Hint: It involves humor and being human, not just another sales pitch).
    • Customer Success vs. Up-Selling: A candid look at what district leaders actually want from edtech partners—relationship-based support rather than aggressive sales tactics.
    • The Digital-Analog Balance: Why a CTO who loves technology still believes in the vital importance of handwriting, face-to-face communication, and soft skills in student development.
    • Shadow and Leap: Amanda’s practical advice for any teacher looking to transition: Find a mentor, shadow the role you want, and don't be afraid to ask for the opportunity.
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    38 mins
  • #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
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