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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 Education Founder’s Blueprint: Kevin Chavous on Turning Setbacks Into Proof Points, Credibility, and Growth That Lasts
Most education founders think buyers want the perfect pitch, the flashy product, or the right political connection.
But Kevin Chavous—national education reformer, bestselling author, and President of Stride, Inc. proves that none of those close deals. What does? Credibility, proof, and persistence.
This episode is extra special because Kevin was the very first guest we ever sat down with when we launched Breaking the Grade back on April 1, 2022. And his message then is even more relevant today for education founders, EdTech companies, and leaders chasing traction in a shifting market.
From losing a mayoral race in D.C., to leading one of the most influential school reform movements in the country, to shaping hybrid learning for millions—Kevin’s story is more than inspiration. It’s a blueprint for how to earn credibility, attract trust, and turn setbacks into traction.
Because here’s the truth: wins show your solution works, and setbacks—if you frame them right—make buyers trust you even more.
In this episode of Breaking the Grade, I sit down with Kevin Chavous and my co-host John Gamba, Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, to unpack the journey behind Kevin’s impact—and why it matters for every founder chasing traction in the education market.
This isn’t just an interview. It’s a founder playbook for turning obstacles into assets, building buy-in that accelerates deals, and creating solutions that students and teachers actually champion.
🔑 5 Big Takeaways for Education Founders
1️⃣ Credibility Comes From the Hard Parts
Kevin’s wake-up call came in a prison where a warden said educating inmates was a “waste of money.” That story became his credibility anchor. For founders, your toughest moments are your most powerful proof points—buyers trust scars, not slogans.
2️⃣ Setbacks Sell—If You Frame Them Right
Kevin’s failed mayoral run didn’t end his influence—it multiplied it. By framing setbacks as fuel, not failure, he turned doubt into trust. Founders who position setbacks as lessons, not failures, win more trust with buyers and partners.
3️⃣ Student Voices = Buyer Signals
“The most dangerous phrase is, ‘We’ve always done it this way.’” Kevin shows why aligning with student needs is the ultimate credibility test for founders.
4️⃣ Community Buy-In Is the Real Multiplier
D.C.’s reform worked because it was built with community voices, not imposed on them. For founders, the same principle accelerates sales: champions in your market generate warmer, faster-moving leads than cold calls ever will.
5️⃣ The One Yardstick That Closes Deals
Kevin’s mantra: “Will this help a child learn?” If you can answer that clearly and back it with evidence, you’ve already handled the biggest objection in the sales process. If not, your pitch stalls.
If you’re still treating setbacks as failures, this episode is your reset. Kevin proves they’re your strongest growth story—and that the first guest we ever hosted on Breaking the Grade back in April 2022 still has the blueprint founders need most today.
📩 DM me “Journey” and I’ll show you how to structure your setbacks into proof points that attract buyers, partners, and investors.
📤 Know a founder struggling to turn challenges into momentum?
Send them this episode—it might save them from quitting too early.
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