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.
Episodes
111 episodes
Targeting That Scales: How the Right Audience Changes Everything
Every growth story looks like it’s about marketing on the surface.But underneath, it’s almost always about one thing: who you’re actually building for.In this episode of EdSales Edge,
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Stop Funding the “Maybe” Trap: You’re Losing $50K in Contracts to Wrong Leads
Ever feel like you’re doing everything right…but your pipeline still isn’t working?You’re having conversations. People respond. It looks promising.And yet… nothing moves.It’s not that you need more leads.You’re spendin...
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When More Kills Deals: Why Simpler Offers Win in Education Sales
More services. More customization. More flexibility.Sounds like value—but it’s often why deals stall.In this live episode of EdSales Edge, Josh Chernikoff, founder of the ...
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From Stuck Deals to Simple Wins: How to make education buyers say yes
“If you have to sell hard, your offer sucks."Josh Chernikoff, founder of the EdSales Elevation Experience, opens this episode with a truth bomb inspired by the
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From Confusion to Clarity (The Offer That Makes People Say “I Need That”)
Deals stall all the time, even after strong conversations. In the education space, this happens every day with superintendents, principals, university presidents, and decision-makers who are interested, but don’t move forward.This live e...
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Why Deals Stall (And How To Keep Them Moving)
If your deals keep stalling after great conversations… it’s not your follow-up.It’s your clarity.In this episode of EdSales Edge, Josh Chernikoff (founder of
Stop Guessing, Start Thriving: Unlocking Clarity in Education Sales
Most education founders think sales success comes from bigger networks or constant activity. In this episode of EdSales Edge, Josh Chernikoff, founder of the
Listen More, Sell More: From $25K Pilots to $100K Partnerships
Many founders in education sales assume success comes from a sharper pitch, a polished deck, or a stronger demo. In this episode of The EdSales Edge, Josh Chernikoff and Paul King reve...
Miss the Signals, Lose the Deal: What Happens When You Don’t Ask and Align
Most founders know listening matters in education sales. But few understand how to structure their questions to uncover real tensions and build trust before pitching. In this episode of EdSales Edge, Josh explains how the dis...
Listen First. Win Later: How Listening Saves Pilots From Failing
Most founders believe winning districts comes down to a stronger pitch.Better deck. Sharper demo. Stronger proof.But in this episode of EdSales Edge, a senior education leader reveals a different problem:Most ...
Listening Beats Pitching in Education (Why Trust Markets Don’t Respond to Noise)
Most founders selling into education think they need more leads.More visibility.More meetings.More activity at the top of the funnel.In this episode, Josh explains why traditional lead generation breaks down in education, ...
How Education Buyers Evaluate Credibility (Why Credentials Alone Don’t Build Trust)
Credibility in education isn’t earned through credentials alone — it’s earned through alignment and believability. In this episode of EdSales Edge, Josh sits down with
Why Most LinkedIn Advice Fails Education Founders (And What Actually Works)
LinkedIn is filled with confident advice about growing audiences and turning posts into sales. But most of that advice was built for fast-moving industries, not for education.In this episode of EdSales Edge, Josh explains why so many edu...
Building Trust with Education Buyers: Why Silence Isn’t Rejection
Rachel Edoho-Eket, President of the Maryland Association of Elementary School Principals, understands that in education, credibility isn’t earned through noi...
Why Chasing “Likes” Keeps You Stuck (How Education Buyers Actually Decide)
Most education founders assume LinkedIn isn’t working because no one is engaging.Posts get views but no likes.Thoughtful ideas land quietly.Weeks go by with no visible signal that anything is happening.In this episode of <...
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Why Selling Software Keeps You Stuck, and Selling Peace Moves Deals
Most education founders would celebrate landing one pilot.Sam and Michael landed nine.In this episode of EdSales Edge, Josh sits down with Samuel Rabkin ...
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Why “What You Do” Isn’t Why Education Leaders Buy
Why is Apple more innovative than everyone else? It’s not better technology; it’s a different way of communicating.In this episode of EdSales Edge, Josh applies Simon Sinek’s "Start With Why" framework directly to education sa...
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Why the Fastest “Yes” Beats the Biggest Budget — with Dr. Brooke Olsen-Farrell
Selling into education rewards clarity, not size. Long cycles, layered decisions, and committee-based buying can quietly drain a founder’s runway, especially when growth is tied to landing “big name” districts.In this episode of EdSal...
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The Perfect Client Paradox: Why Chasing More Leads Isn’t the Answer
Most education founders think they have a lead problem. You want more emails, more demos, more top-of-funnel activity.But here is the hard truth: You don't have a lead problem; you have a perfect client problem. If you are chasing the...
Breaking Up with Breaking the Grade (and Why It Was Time)
We built Breaking The Grade to challenge the status quo. We spent four years inspiring you to think differently about education. We interviewed visionaries, we debated policy, and we celebrated the "idea" of change.But here is t...
Best of 2025: How Education Founders Can Turn Any Conference or Summit Into a Sales Engine That Builds Trust, Authority, and Pipeline
Some episodes don’t just inspire, they show you what execution really looks like.This one’s a real-time playbook in action.Originally LIVE from the University of Toronto at the Canadian EdTech Summit on 3...
Best of 2025: Karim Kuperhause & Rose Hastreiter on Why Education Founders Must Sell First, Master Objections, and Build a Repeatable Process Before Delegating or Scaling
Some episodes can't just be missed… this one is one of them. Why? Because it shifts how education founders think about sales, delegation, and building predictable pipelines. Originally streamed as a LinkedIn Live in Octo...
Best of 2025: Robert Martellacci on How Education Founders Stuck Chasing Sales Can Turn Relationships, Setbacks, and Partnerships Into Scalable Credibility and Revenue Growth
Some episodes don’t just share insights, they show education founders how to turn relationships, strategy, and innovation into measurable results. This one did.Robert Mart...
Best of 2025: Jolene Levine on How Education Founders Can Turn Betrayal, Burnout, and Chaos Into a Blueprint for Credibility, Alignment, and Lead Flow That Converts
Some episodes don’t just start conversations, they shift how education founders think about credibility, leadership, and lead generation. This one did.When Jolene Levin,...
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Best of 2025: John Gamba on How Education Founders Can Rebuild Trust, Visibility, and Pipeline Through Authentic LinkedIn Strategy
Some episodes don’t just offer sales tactics; they redefine how education founders think about visibility, trust, and lead flow. This one did.When John Gamba joined Josh for a ca...
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