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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
Stop Pitching: What Actually Gets a Superintendent’s Attention
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
The fastest way to lose trust is to try to earn it too quickly.
That's a difficult reality for education companies.
Dr. Jared Bloom sees it every day.
As Superintendent of Franklin Square School District in New York, Jared receives hundreds of emails every day from companies trying to get his attention. Most never get a response.
Not because the products are bad.
Because that's not how trust gets built.
In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine sits down with Jared for an unusually honest conversation about what actually gets a superintendent's attention—and why most education sales outreach misses the mark.
Jared explains why cold emails rarely stand out, why generic LinkedIn pitches feel transactional, and what separates a vendor from a true partner.
He also shares how districts evaluate new solutions and why some companies earn long-term trust while others never make it past the first conversation.
For founders, sales teams, and customer success leaders, this episode offers a rare opportunity to hear directly from the other side of the table.
WHY THIS MATTERS
Most education companies assume they have an outreach problem.
In reality, many have a trust problem.
When relationships are weak:
- Every sales conversation feels harder
- Follow-up becomes chasing
- Pilots stall
- Adoption slows
When trust exists:
- Conversations happen faster
- Feedback becomes honest
- Internal champions emerge
- Partnerships last longer
The strongest education sales strategies aren't built around volume.
They're built around credibility.
KEY STRATEGIES & MENTAL MODELS
1️⃣ Relationships Scale Better Than Outreach
The goal isn't more conversations.
The goal is stronger conversations with the right people.
2️⃣ Relationships Are Built In Real Conversations
Face-to-face interactions allow education leaders to understand who they're working with—not just what they're buying.
3️⃣ Start Small, Then Expand
Successful districts start with small pilots, gather evidence, and expand only after results are visible.
4️⃣ Teacher Buy-In Matters
Even the strongest product can fail if the people using it don't believe in it.
5️⃣ Partnership Continues After The Sale
The most successful companies stay involved, listen closely, and adapt based on district feedback.
WHO THIS EPISODE IS FOR
- Education founders struggling to break into districts
- EdTech sales teams relying heavily on cold outreach
- Customer success leaders focused on retention and adoption
- Companies looking to build long-term district partnerships
- Anyone selling into K-12 education
🚀 NEXT STEP
Ask yourself:
Are you spending more time increasing outreach...
or increasing trust?
Because schools rarely buy from strangers.
They buy from partners.
Text "RELATIONSHIP" to 771-333-4233.
🔁 SUBSCRIBE & SHARE
Follow EdSales Edge and share this with someone who thinks more outreach is the answer.
Sometimes the real answer is building better relationships.
Connect with Josh Chernikoff
Founder, Edsales Elevation Experience
Host, Edsales Edge Show
🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/
📩 Email: Jc@joshchernikoff.com
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