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Description
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.
106 Episodes
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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 EdSales Elevation Experience) breaks down why deals don’t die at the end, they fall apart at the beginning, when your offer isn’t clear enough to survive without you. He’s joined by Edwin Blanton, Ph.D., Assistant Vice Provost at The University of Texas at San Antonio, who shares the shift that changed everything. Instead of offering 1...
Most education founders think sales success comes from bigger networks or constant activity. In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Elevation Experience (3E), flips that assumption. He shows why clarity about who you serve, what you solve, and the results you deliver drives consistent, high-converting sales. Josh answers common questions from founders in 3E, a program designed to build repeatable, clarity-driven sales systems. He breaks down whether networks ...
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 reveal a different truth: strategic listening beats persuasive talking. Paul King, Founder of Neighborhood Educational Partners (NEP), shares how shifting from explaining to understanding transformed his business. By listening first, he increased confidence, turned pilots into year-round partnerships, and opened new...
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 discipline of journalism — inspired by Terry Gross, host of NPR’s Fresh Air since 1975 — became the foundation for his education companies and the Raise Your Hand campaign, now used by hundreds of education vendors. Terry Gross isn’t loud or flashy. Her interviews succ...
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 vendors never ask what the system actually needs. Josh sits down with Ryan Donaghy, Deputy Minister of Government, New Brunswick, Canada. Ryan is pitched constantly — AI tools, tutoring platforms, and “transformational” solutions. Yet one pattern appears again and again. Vendors talk....
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, and introduces Raise Your Hand as a different kind of lead generation strategy built for trust-based markets. Instead of chasing calls or pushing urgency, Raise Your Hand is designed to generate voluntary buying signals from decision-aware leaders. It filters for readine...
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 Dr. Tara Williams, Founder of Innovative Collegiate Consultants, Inc. to explore a positioning shift most education founders avoid: When you share your struggles clearly and intentionally, people trust you more. Dr. Tara holds a PhD, earned tenure, and built programs at the college level. But her credibility accelerated w...
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 education founders feel frustrated and stuck on LinkedIn, even when they follow all the popular strategies. He breaks down how education buyers actually evaluate credibility and why likes, comments, and visibility rarely translate into real influence. Instead of...
Rachel Edoho-Eket, President of the Maryland Association of Elementary School Principals, understands that in education, credibility isn’t earned through noise or constant visibility — it’s earned through consistent, observable behavior over time. As a principal and state-level education leader, Rachel has seen founders and vendors make the same mistake repeatedly: talking too much, posting too often, and confusing activity with trust. In this episode of EdSales Edge, Josh sits down with Rach...
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 EdSales Edge, Josh explains why that silence isn’t rejection — it’s evaluation — and introduces two mental models that change how founders understand credibility in education: the Conference Model and the Gym Model. This episode isn’t about posting more, going viral, or g...
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 and Michael Mahoney, co-founders of Mediator Spark, to unpack how clarity around their Perfect Client led to a sharper Signature Solution—and why that clarity turned stalled conversations into fast-moving pilots. This isn’t a story about selling software or education theory. It’s a case study in what happens when founders stop explaining to...
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 sales. For early-stage founders (<$2M revenue), school leaders aren't just buying software or curriculum. They are buying you. They are buying your judgment, your conviction, and your belief. This episode explores why clarity of belief is the fastest rout...
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 EdSales Edge, Josh sits down with Dr. Brooke Olsen-Farrell, a nine-year Superintendent at Slate Valley Unified School District and a national policy leader. Together, they unpack why traction in education doesn’t start with the biggest budgets, it starts with the Per...
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 wrong person, no amount of lead gen will fix your revenue. It just gives you more conversations that don't convert. Traction comes from the "Clean Window" strategy. Instead of trying to convince skeptics to care, you need to target the buyers who already value ...
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 the hard truth I finally had to face: Inspiration does not pay your payroll. Over the last 12 months, I listened closely to what you, the founders, the sales leaders, the operators, were actually asking me in private. You didn't need more "inspiration." You needed Clar...
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 30th October, 2025, Josh breaks down exactly how education founders can stop wasting time and money at conferences, and start turning them into revenue-driving machines. After two decades in education and sales leadership, Josh has learned one thing: conferences don’t grow your business, a c...
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 October 2025, this replay brings back one of the most tactical, mindset-shifting conversations of the year. When Karim Kuperhause, CEO and Founder of HierSales, joined Josh for a candid LinkedIn Live conversation, later joined by Rose Hastreiter, founder and CEO of Leo...
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 Martellacci, founder and president of Mindshare Learning Media, has spent 25 years shaping Canada’s EdTech ecosystem, mentoring leaders, and creating opportunities for companies to scale. From launching Kevin O’Leary’s school division to moderating the Canadian EdTech Summit, Robert has seen firsthand how trusted relation...
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, entrepreneur, innovator, and founder of NorvaNivel, shared how she built a global company, scaled too fast, got fired from her own business, and rebuilt from the ground up, it became one of the most replayed and quoted episodes of the year. Her story hit home for education founders who’ve seen their pipeline stall or partner...
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 candid LinkedIn Live conversation, it wasn’t just another talk about personal branding; it was a deep dive into how education founders can turn an authentic online presence into real-world partnerships, pipeline, and predictable revenue. John, entrepreneur, investor, long-time education innovator, and Entrepreneur in R...
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