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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
$9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore
Most education founders don’t fail because of bad ideas.
They fail because they lean too hard on “AI-powered” buzzwords, skip the research-to-practice proof buyers demand, and don’t form the partnerships that give them credibility and attract the right leads.
That’s the cycle YourWay Learning set out to break.
Back in January, at the IFE Conference in Monterrey, Mexico, I sat down with Jaime Palés, co-founder and president of Yourway Learning, with 20+ years of global experience scaling educator training and AI-driven learning models— and Michael Golden, Vice Dean of Innovative Programs and Partnerships and Executive Director of Catalyst at Penn GSE and ex-Microsoft exec
At the time, YourWay was still early—focused on building with intention, grounding in research, and designing tools teachers would actually use.
Fast forward: they’ve raised $9 million and launched a partnership with Penn GSE turning credibility and strategic alignment into a pipeline of opportunities.
This episode takes you back to that conversation—before the headlines—showing how YourWay built the foundation that turned momentum into investments and qualified leads.
5 Big Takeaways for Education Founders
1️⃣ AI Isn’t the Differentiator—Your Approach Is
Buzzwords don’t close deals. Clear, outcome-driven solutions do and they attract schools, districts, and buyers actively looking to invest.
2️⃣ Research to Practice = Credibility
Buyers don’t want “feel good” workshops. They want evidence your AI or EdTech solution drives measurable classroom impact—your strongest lead-generation tool.
3️⃣ Your DNA as a Founder Matters
Persistence, humility, and community separate ventures that scale from those that fade—especially in the long sales cycles of education.
4️⃣ Partnerships Trump Solo Play
The fastest path to traction is aligning with research institutions, accelerators, and trusted partners who validate your model—and bring you in front of qualified buyers.
5️⃣ Mission + AI + Partnerships = Long-Term Wins
Quick cash grabs don’t last. Buyers back founders who balance innovation with credibility and sustainability.
YourWay’s story proves that when vision, credibility, and timing align, momentum turns into millions. The lesson is clear: lead with outcomes, use AI with intention, and anchor growth in partnerships that last.
📩 DM me “Momentum” and I’ll show you how to structure your growth story so buyers and investors notice—and respond.
📤 Know a founder chasing buyers with AI hype but no real partnerships?
Send them this episode. It might save them from losing deals before they scale.
✍️ Love the show?
Subscribe on Apple Podcasts and Spotify so more education founders can turn AI innovation + strong partnerships into consistent sales growth.
#EdTechSales #FounderLedGrowth #AIinEducation #PartnershipsThatScale #ResearchToPractice #SalesStrategy #GrowthStrategy #BreakingTheGrade #EdSales
