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
From “Great Pitch” to Signed Contract: Paul Vallas on the Buyer’s Lens That Closes Education Deals
What happens when you finally land the big meeting… and walk out with nothing but “We’ll think about it”?
It’s the growth killer most founders don’t see coming—your pitch isn’t aligned with how education buyers actually make decisions.
That’s why this live Breaking the Grade episode from ASU-GSV (the edtech conference each April in sunny San Diego) is such a win: I sat down with Paul Vallas——nationally recognized education leader, former superintendent of Chicago, Philadelphia, and New Orleans, CEO of the Recovery School District after Hurricane Katrina, and co-founder of both Vallas Group Inc. and Global Educator
And here’s why his perspective can change your sales game:
✅ He’s overseen multi-billion-dollar budgets and made the final call on which solutions get funded.
✅ He’s rebuilt entire school systems in crisis and driven record student gains in districts with 80%+ poverty rates.
✅ He’s been pitched thousands of times—and knows exactly why most vendors fail.
And here’s the kicker: Paul isn’t just sharing his story. He’s pulling back the curtain on the decision-making framework education buyers actually use before they say “yes.”
If you’re chasing deals in the education market, this conversation shows you how to go from “great product” to “signed contract.”
5 Big Takeaways for Education Founders
1️⃣ The 3-Point Test Every Buyer Uses
Quality, fit, scalability—miss one, and the deal dies.
Know where you stand before you pitch.
2️⃣ The Core Priorities Every Buyer Protects
Every buyer looks for certain fundamentals—curriculum strength, data use, interventions, support, time on task.
Tie your solution directly to these.
3️⃣ Why Misaligned Products Get Cut First
Misaligned programs are the first to go in a budget cut.
Position yourself as mission-critical, not optional.
4️⃣ How to Make Your Offer Budget-Proof
Solutions tied to measurable outcomes survive funding shifts.
Prove your link to results that matter most.
5️⃣ The Right Way to Start the First Conversation
Your opening determines whether you move forward or get brushed off.
Use approaches that earn a real next step.
If your deals keep stalling at “interested,” this episode gives you the buyer’s-eye view you need to close smarter and faster—straight from one of the most respected education leaders in the U.S.
📩 Want help structuring your pitch so education buyers say “yes”?
DM me “Close” and I’ll walk you through it.
✍️ Love the show?
Subscribe on Apple Podcasts and Spotify so more founders can close bigger, better deals.
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