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 do...
The Clarity That Came After the Pause
Every education founder eventually hits a point where their sales system has to evolve.
For Josh Chernikoff, founder of EdSales Revenue Machine, a forced pause and triple bypass surgery accelerated that shift.
It starts from a personal health moment, but this episode isn’t a medical story—it’s a sharper lens on how education companies build growth that actually lasts.
This episode introduces the EdSales Revenue Machine (formerly EdSales Elevation Experience): a rebuilt framework focused on speed, support, and implementation — not more information.
Josh breaks down a simple truth: more activity...
Getting on First Base: An Education Founder’s Guide to Sustainable Growth
Most education founders think growth comes from landing the biggest district.
Wrong.
In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Elevation Experience returns just 17 days after unexpected triple bypass surgery and gives an update to the community on his recovery and the long road ahead.
John Gamba, Entrepreneur-in-Residence at Penn GSE, joins on his birthday on Wednesday for a breakdown of Moneyball by Michael Lewis (and the film...
What I Wish More Education Founders Knew About Their Leads
Some of your best opportunities aren’t missing.
You’re just looking in the wrong places.
In Moneyball, Michael Lewis told the story of how the Oakland A’s competed against richer baseball teams without the same budget or star players. Instead of chasing obvious talent, Billy Beane, GM of the Oakland A’s team used data and pattern recognition to spot undervalued players other teams overlooked.
That shift changed baseball.
And it holds a powerful lesson for education sales.
Most founders think growth comes from more leads, more outreach...
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, John Gamba, Entrepreneur-in-Residence at Penn GSE, steps in at the wheel as Josh Chernikoff, founder of the EdSales Elevation Experience and host of the EdSales Edge continues recovering after a successful surprise triple bypass surgery. Josh is doing well, resting, and on the mend, with John—his best friend and co-host—carrying the conversation forward until he returns.
Joined by Celine Xu, founde...
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 spending time on the wrong ones.
In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Elevation Experience breaks down the shift most education founders avoid:
Not every opportunity deserves your time.
Warren Buffett built his investing philosophy on this, he doesn’t chase every opportunity, he filters for w...
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 EdSales Elevation Experience and John Gamba, Entrepreneur-in-Residence at Penn GSE break down a hard truth: adding more makes your offer weaker.
Most education founders try to win by doing more—more features, more options, more ways to say yes. But buyers want the opposite: clarity, focus, and a clear outcome.
Deals don’t fall apart at the end—they fall apart the moment your offer...
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 Alex Hormozi school of business: deals don't die at the finish line; they die the second you introduce a weak offer.
Most education founders are busy tweaking pitch decks and chasing leads, but they’re ignoring the Hormozi fundamental: creating a "Grand Slam Offer" so good that people feel stupid saying no. In education sales, your offer doesn’t stop with you—it has to make sense when your buyer r...
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 episode of EdSales Edge dives into the real reason why: stalled deals aren’t about follow-up, they’re about clarity. When your message isn’t clear, it doesn’t travel. And in education sales, your buyer isn’t the final decision-maker, they’re the one carrying your message into rooms you’re not in.
Josh Chernikoff, founder of the EdSal...
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 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 1,000+ training options, Edwin built a clear Signature Solution his...
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 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 can replace systems, why outreach stalls even with responses, how to know if you’re ready for structure, and what makes 3E di...
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 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 district contracts, including work in juvenile detention facilities.
The episode breaks down the “Raise Your Hand” framework. Not scripts, a mindset: lead with curi...
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 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 succeed because of preparation, curiosity, and thoughtful questioning.
Josh shows how those same principles...
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 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. Almost none listen.
They arrive with s...
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, 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 readiness by lowering risk.
Education buyers rarely say “no.”
They delay.
They stay...
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 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 when she stopped leading with her résumé and started leading with her...
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 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 treating LinkedIn as a conversion funnel, Josh shows how to use it as a long-term credibility system built on...
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 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 Rachel in a live interview recorded at FETC in Orlando to break down how education buyers actually evaluate credibility — and why...
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 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 gaming the algorithm.
It’s about understa...
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 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 tools and start enroll...
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 sales.
For early-stage founders (
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 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 Perfect Client.
If you’re stuck chasing prestige logos while momentum stalls, this conversation will help you r...
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 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 the outcome.
In this...
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 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 Clarity.
You were tired of guessing who the decision-maker actually is.You were...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 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 conference strategy does.
From DC Star...
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 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 Leon...
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 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 relationships and ecosystem buy-in drive both impact and revenue.
In this c...
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, 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 partnerships implode. Because behind every funding round or fast scal...
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 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 Residence and Director of Innovative Programs at Penn GSE, broke down how...
The Gratitude Episode: 22 Guests, 63 Countries, and a Community That Turned 2025 Into Our Most Meaningful Year Yet
Most founders rush to the next metric, the next meeting, the next milestone.
But the truth is: you can’t scale what you don’t stop to appreciate.
This episode is different.
It’s the last show of 2025.
It’s the Thanksgiving episode.
And it’s the moment we zoom out, breathe, look at the year we built together, and acknowledge every founder, leader, innovator, and listener who carried this show to its biggest year yet.
This isn’t a highlight reel.
It’s a gratitude letter.
To...
The Headline Mistake: How eight words on LinkedIn unlocked a $100k repeatable pipeline.
Most education founders think their LinkedIn headline is just a formality.
A place to drop their title. List their company. Maybe add “passionate about education.”
But here’s what they’re missing: your headline is where credibility begins. Where confidence starts. Where clarity is born.
And when you nail those three? Everything else follows. Your LinkedIn sharpens. Your offer becomes clear. Your messaging finally lands with the buyers you’ve been chasing.
But getting your headline right? That’s the hard part.
It seems simple, just 220 characters, right? But distilling y...
Hesitation Is a $250K Mistake: Dr. Tamara Minott on How Education Founders Close Deals With Confidence
Most education founders don’t lose deals because their product isn’t good enough.
They lose them because they hesitate, overthinking the pitch, second-guessing decisions, and waiting for “perfect” when progress is all they need.
That hesitation kills more deals than rejection ever will.
And if you’ve ever felt imposter syndrome creeping in before a big call or proposal, you already know how fast confidence cracks under pressure.
Dr. Tamara Minott, PhD, “Dr. T”, knows that feeling well.
Before becoming the Director of College & Career Readiness at Coney Isl...
You Crushed the Demo—But Still Can’t Close: The $100K Mistake Education Founders Keep Making
You crushed the demo.
The buyer smiled. They nodded. They even said, “This is exactly what we need.”
And then… nothing.
That silence isn’t harmless. Every “We’ll be in touch” costs you weeks of follow-up, lost momentum, and deals that should already be on your books.
In Part 1, “Your Demo Is the Problem” with John Gamba, Entrepreneur in Residence and Director of Innovative Programs at Penn GSE, Josh and John exposed a hard truth: most EdTech demos fail before they even start. Founders pitch products, not pain. They confuse polish for persuasion. Head n...
From Betrayal and Courtroom Battles to Closed Deals: Robespierre Reyes on Rebuilding Credibility, Team Alignment, and Education Deals That Close
Robespierre Reyes had funding, traction, and a winning idea.
Then came the lawsuits, burnout, and partners who betrayed him.
Four companies, three failures, one courtroom showdown. His confidence, credibility, and pipeline of leads were all at risk.
Most founders would quit. Rob didn’t.
Instead, he rebuilt everything that actually drives qualified leads and closed deals, team alignment, credibility, and trust, with radical honesty, clear boundaries, and a repeatable playbook for education founders.
Josh met Rob at the IFE Conference in Monterrey, Mexico. After sharing a panel, th...
From Confusion to Clarity: JD Mosley-Matchett on the Message Shift That Turns Unclear Offers into Scalable, Trust-Building Growth for Education Founders
Most education founders and EdTech leaders think their problem is marketing.
But sometimes, the real issue is something more critical: Clarity
If your message isn’t clear, your market stops listening, no matter how brilliant your solution is.
That was the hard truth J.D. Mosley-Matchett, PhD had to face.
As the Founder & CEO of InforMaven.AI, JD’s mission was bold: help underfunded, overregulated colleges and universities harness the power of AI to operate more efficiently.
But even her biggest supporters couldn’t answer the qu...
The Mindset Reset: Mitch Weisburgh On How Education Founders Can Master Mindset, Beat Burnout, and Close Strong Deals
You’ve got the product, the drive, and the skills, but when pressure hits, your mindset starts to crack.
Suddenly, deals stall, momentum fades, and even your warmest prospects go quiet. The harder you push, the less it seems to move forward.
Most education founders panic. They double down on demos, CRMs, late nights, and new pitches, thinking more effort will fix it.
🚫 Big mistake.
When your mindset cracks, hesitation costs contracts, fatigue kills momentum, and fear turns every objection into self-sabotage.
That’s why this episode of Brea...
Stop Delegating Sales: Why Education Founders Must Sell Their Solution First Or Watch Their Pipeline Die
Most education founders think the next rep, agency, or AI tool will solve their sales problem. It won’t.
Here’s the truth: if you can’t sell your own offer clearly, no one else can. Every lead you hand off too early is wasted time, lost money, and a pipeline headed for collapse. Every day you delay founder-led sales is another day your growth stalls and another day your competition pulls ahead.
In this episode of Breaking the Grade, you’ll hear the reset education founders don’t want but desperat...
From Lost Leads to Locked Contracts: Paul King on Niche Focus, Pilots That Convert, and Closing Education Deals
What happens when you stop trying to serve every school and start solving one urgent problem for the right schools?
It’s the positioning shift most founders resist—but it’s the exact move that transforms “just another vendor” into a mission-critical partner.
That’s why this episode of Breaking the Grade is essential listening: Josh sits down with Paul King—Founder & Director of Neighborhood Educational Partners (NEP) and Founder of King Education, who pivoted from one-on-one tutoring to landing public school contrac...
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, an...
The Guarantee Shift: Karim Kuperhause on How Education Founders Build Trust and Win Qualified Leads Without Sounding Desperate
What happens when a superintendent or a higher ed leader—looks you in the eye and asks:
“What happens if this doesn’t work?”
For most education founders, that’s the deal-killer moment. They freeze. They dodge. They hide behind buzzwords. And the buyer walks away unconvinced.
But here’s the truth: In today’s market, whether it’s K–12 districts or higher ed institutions, leaders don’t buy hope—they buy guarantees.
That’s why this episode of Breaking the Grade could be one of the most important we’ve ever released. I sat...
From Invisible to Irresistible: Michael Campbell on Using Research and Proof to Build Trust, Generate Leads, and Drive Education Growth
Every education founder, EdTech CEO, and school leader wants growth. But here’s the mistake almost everyone makes: they chase revenue before they’ve earned trust.
In education, trust is the real currency—it turns a pitch into a meeting, and a meeting into a deal.
In this episode, I’m joined by Michael Campbell, president of Advancing Global EDU, Inc., Chief Executive Officer of Dual Bridges Academy and Advisory Board Member at edWeb.net, LIVE from the ASU-GSV Summit (the edtech conference each April in sunny San Diego) —to unpack why rushing to hire sa...
