EdSales Edge Show
EdSales Edge is the strategy podcast for education founders, consultants, operators, and leaders selling into education.
For years, this show was known as Breaking the Grade, a space to challenge the status quo in education and think differently about how change actually happens. That mission hasn’t changed.
But the work has.
Over time, one thing became clear:
Education founders don’t just need inspiration.
They need clarity.
They need real strategies for selling into schools.
They need predictable ways to generate leads.
And they need to understand how trust is built in a system that doesn’t move fast, and doesn’t give many second chances.
EdSales Edge was rebuilt to match that reality.
Hosted by Josh Chernikoff, a two-time education founder who’s built and exited companies in this space, the show breaks down how selling into education actually works—across B2C, B2B, B2B2C, and B2E—always through the lens of how education institutions really make decisions.
This is not a show about hacks, shortcuts, or quick wins.
Education doesn’t work that way.
On EdSales Edge, you’ll hear:
- Real strategy for selling into education systems
- Conversations with education decision-makers who explain how buying actually happens from the inside
- Stories from founders, CEOs, and operators who’ve built real traction selling into schools—what worked, what didn’t, and what actually moved deals forward
- Teachings from the EdSales Elevation Experience, the system used to help education founders move from unclear and invisible to trusted and in demand
You’ll learn how to:
- Define your Perfect Client
- Pull the right credibility lever
- Move from being hidden… to trusted… to building a real lead engine
Josh is joined by his good friend and mentor, John Gamba—Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, and a former education founder who’s led companies through real growth and successful exits. John brings the institutional lens, shaped by years inside districts, universities, and education systems, seeing how decisions get made when the doors are closed and what earns trust over time.
Together, they sit on both sides of the table, the builder side and the system side, so the show stays grounded in reality, not sales theory.
If you sell into education and you’re tired of guessing,
guessing who to talk to,
guessing how decisions get made,
guessing why interest doesn’t convert—
this show is built for you.
EdSales Edge
Clarity. Credibility. Real traction.
If you sell into education, this is where you earn your edge.
EdSales Edge Show
What is Breaking the Grade?
The future of the world’s classroom is falling into our hands. How can we help shape the next generation to learn more and live better than we do today?
This type of change won’t come from repetition. We need to BREAK the education industry if we want its EVOLUTION to take place.
That's why we’re working to Break the Grade.
The future of the world's classroom is falling into our hands. How can we help shape the next generation to learn more and live better than we do today? This type of change won't come from repetition. We need to break the education industry if we want its evolution to take place. That's why we're working to break the grade. Hello, breakers and difference makers. I'm Josh Chernikoff, host of How I Broke That, and a two-time entrepreneur in the education industry that has successfully exited both companies. I've experienced my share of big breaks in life, and I'm bringing my signature approach into the open as we begin breaking the grade. I'm embarking on this journey alongside my good friend and mentor, John Gamba, entrepreneur in residence and director of innovative programs at Penn's Graduate School of Education. In our podcast, you'll hear from emerging business owners in the education space who are working to shape brains for the better. From art to tech, finance to science, we'll listen to powerful, personal stories from experts in every corner of learning. Tune in as we hear about industry trends, unique methods, and tools, and the attempts that have and haven't worked for our grade-breaking guests. How is technology being used for the better? Our gamified program's the key to student engagement. Is project-based learning all it takes to ensure our lessons stick around for real-world use as the years go on? What about good old hard work and honesty? Where do those traits fall into play? We'll share behind the desk details of every idea, failures, and successes alike. And last and certainly not least, we'll provide you with the inspiration and motivation you need to go out and make a change of your own in this space. So, fellow entrepreneurs and educators, what do you think? Are you ready to dive in as we break the grade, changing the learning world for the better with every single step we take together?
