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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
The Guarantee Shift: Karim Kuperhause on How Education Founders Build Trust and Win Qualified Leads Without Sounding Desperate
What happens when a superintendent or a higher ed leader—looks you in the eye and asks:
“What happens if this doesn’t work?”
For most education founders, that’s the deal-killer moment. They freeze. They dodge. They hide behind buzzwords. And the buyer walks away unconvinced.
But here’s the truth: In today’s market, whether it’s K–12 districts or higher ed institutions, leaders don’t buy hope—they buy guarantees.
That’s why this episode of Breaking the Grade could be one of the most important we’ve ever released. I sat down with Karim Kuperhause— former teacher, founder of 3 tutoring centers + 32 satellite programs, and now CEO of HierSales, the company helping education organizations build outcome-based guarantees that change the game.
Karim isn’t just talking theory. He’s building the future. Because the future of education sales—from classrooms to campuses—is guarantees. Superintendents, districts, universities, and decision-makers at every level won’t keep gambling on “maybe.”
They want confidence.
They want results.
They want partners willing to shift the risk.
And guarantees are how you deliver it.
🔑 5 Big Takeaways for Education Founders
1️⃣ Why Founders Lose Deals They Could Win
Ducking the “failure” question signals you don’t believe in your own product.
2️⃣ The 3-Part Framework for Guarantees
Outcome. Timeline. Safeguard. Build these in, and you win trust before you pitch.
3️⃣ Why Pilots Build Trust Faster Than Promises
Districts are risk-averse. A low-cost pilot proves you work and builds confidence without big commitments.
4️⃣ Guarantees Double as a Client Filter
A strong guarantee doesn’t just attract buyers—it shows you who’s serious. If they won’t even test, they’re not your client.
5️⃣ Why Guarantees Beat Demos
Demos impress no one. Outcomes and guarantees close deals.
If your deals keep stalling at “interested” but never closing, this is your wake-up call. Guarantees aren’t optional—they’re the future of selling in education.
📩 DM me “Guarantee” and I’ll show you how to structure offers that build trust and filter perfect-fit clients.
📤 Know a founder still hiding behind buzzwords instead of outcomes?
Send them this episode—it might save them from losing their next big deal.
✍️ Love the show?
Subscribe on Apple Podcasts and Spotify so more founders can close bigger, better deals.
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