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.

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.

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.

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 learners.

• The Emotional Toll: Jess discusses the very real teacher guilt associated with leaving the classroom and how she navigated the feeling that she was abandoning her students to prioritize her own growth.
• Redefining Just a Teacher: How Jess overcame the stigma that ECE educators are babysitters and recognized that managing a classroom of four-year-olds requires elite-level project management and negotiation skills.
• Finding Your Tribe: The importance of finding an organization (like Frog Street) that shares your educational values so the transition feels like an evolution of your calling, not a departure from it.
• The Learning Curve: Jess shares her experience tackling the corporate learning curve—from mastering new software to understanding business travel—and why a teacher’s figure-it-out attitude is the ultimate corporate superpower.
• Scaling Your Impact: A look at her role as Senior Director of Professional Learning and how she uses her classroom experience to design training that actually respects and engages educators.

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 where almost everyone is a teacher.
• The First Step: Why Maggie’s transition began with an entry-level "Sales Support Assistant" role and the importance of being open to learning new corporate skills (like Excel!) from the ground up.
• Your New Classroom: How a teacher's "nurturing" quality is a powerful and directly transferable skill for supporting and enabling internal teams.
• Empathy as a Strategy: Maggie explains why she intentionally built relationships with other departments—from the field sales team to the warehouse—to understand their challenges and become a more effective partner.
• Learn By Doing: A look at her current role at Carnegie Learning and how they support teachers with professional development that puts educators in the student's shoes.

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 Conversation:

• What is YouScience? Ivey explains how the platform uses gamified, aptitude-based assessments—not just interest inventories—to provide students with a robust profile of their natural talents and connect them to fulfilling career paths.
• The Power of Strengths: The conversation highlights the profound impact of helping students understand what they’re naturally good at. This approach can build confidence, provide hope, and empower them to make intentional decisions about their future.
• An Unconventional Path: Ivey details her decision to leave her role in college counseling, take a "gap year" to explore different paths (including becoming a certified thermographer!), and how that period of discovery ultimately led her to YouScience.
• Following Your Intuition: A key theme is the importance of listening to your gut. Ivey knew she needed a change and acted on it, eventually reaching out to YouScience because she felt a deep connection to their mission.
• Grounded Advice for a Career Change: Ivey reminds listeners that "the grass isn't always greener." She advises teachers to explore their options but also to focus on "watering the grass where you are"—finding fulfillment and purpose in your current role while thoughtfully considering your next steps.

Resources Mentioned:

• YouScience: A game-based career assessment and guidance platform.
• Gallup Strengths (formerly StrengthsFinder): An assessment tool Ivey credits as a game-changer in understanding her own talents.

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 coaching teachers.

In this episode, you'll hear:

• The story of Laura's "principal pivot" and how the operational realities of the job—from stuck flags to broken bathrooms—led her to seek a change.
• Laura's core advice for educators: conduct a self-inventory to identify what truly drives you versus what weighs on you, and seek a role that aligns with that passion.
• How a chance encounter at an ISTE conference led to her first role in EdTech as a "Director of Teacher Happiness," highlighting the importance of networking and being open to opportunity.
• Insight into the variety of roles at an EdTech startup and how Laura’s position at LiveSchool allows her to impact everything from pre-sales and support to customer success.

The Always A Teacher podcast is for educators who are considering a transition from the classroom to the EdTech industry. Host Matt Gambino, founder of Propel Skills, the number one sales training firm serving EDU and EdTech businesses exclusively, taps into his network to bring you the stories, secrets, and skills you need to make the move.

Learn more about sales training for your EdTech team at propelskills.com.

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 successfully pivot her career.

In this episode, you'll hear:

• A breakdown of the "soft skills" that make teachers exceptional candidates, from managing diverse stakeholder expectations to the art of training.
• Practical, step-by-step advice for educators "noodling on the idea" of a change, including how to analyze job descriptions to identify key technical skills.
• The critical importance of learning how to "translate" a teacher's resume into a corporate one, with specific examples of how to quantify classroom achievements.
• Why informational interviews are a powerful, low-stakes tool for building your network and learning about different roles in the EdTech space.

The Always A Teacher podcast is for educators who are considering a transition from the classroom to the EdTech industry. Host Matt Gambino, founder of Propel Skills, the number one sales training firm serving EDU and EdTech businesses exclusively, taps into his network to bring you the stories, secrets, and skills you need to make the move.

Learn more about sales training for your EdTech team at propelskills.com.