Always A Teacher Podcast
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.
Always A Teacher Podcast
#027 Jess Hammond: Senior Director of Learning and Development
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
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.
