EdSales Edge Show

A superintendent is not a lead generation strategy. Neither is a curriculum director, a principal, or a dean. Those titles tell you who someone is. They don't tell you why they'd care about your solution right now. In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, compares two superintendents who look identical on paper. Superintendent A just renewed a three-year contract, so nobody's pushing for a new solution. Superintendent B's board just made ...

You’re afraid that getting too specific about your perfect client will shrink your market. But what if it does the opposite? In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine and John Gamba, Entrepreneur-in-Residence at Penn GSE challenge education founders to rethink the way they define their target customer—and why “ideal client” may not be specific enough. “Schools” is a market. “K-12 schools” is more specific. But what happens when you keep narrowing...

What if your best customer isn't actually your perfect client? Josh Chernikoff learned this lesson while building his second business, an afterschool enrichment company. At first, he pursued schools that didn't have enrichment programs. They wanted a program—but they didn't necessarily need one. The difference changed everything. When Josh started working with schools that genuinely needed a program, he understood their problems, spoke their language, and could see the world from their perspe...

You can love your solution and still make it incredibly hard to buy. Because your school buyer is wondering what happens to them if they say yes and you are wrong. The Department of Education just released new guidance on responsible technology use. And buried inside it? Five questions every education founder should probably be able to answer before walking into their next sales conversation. That’s why, in this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Mac...

AI can research the district. It can write the email. It can prepare the meeting, summarize the conversation, draft the proposal, and even write the follow-up. So what exactly are you bringing to the sale? In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, challenges education founders and teacherpreneurs to rethink how they use AI in their sales process. This isn't anti-AI — Josh uses it every day. The problem is convenience quietly making strategic dec...

You found the competition. You looked at the application. Then you told yourself: "We're not ready." And maybe you're right. But what if that's exactly why you should apply? In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, challenge one of the most common excuses education founders and teacherpreneurs make: waiting until they feel ready before putting their business in the arena. Because compe...

An education company almost always starts with one person: a founder, a teacher, or a practitioner who saw a problem and decided to solve it. Then something strange happens. The very person who built the solution disappears behind logos, fonts, taglines, company pages and carefully polished messaging. Meanwhile, buyers are asking a much simpler question: "Who are you, and why should I trust you?" That's where deals are won or lost. You don't need a better logo. You need more conversations. Yo...

"We're going to stick with what we have." Every education founder has heard those words. Usually right after their strongest pitch. Usually after a great conversation. Usually after showing hard proof that the thing works. And that's exactly what makes it sting. Most education founders think they lost to another company. They didn't. In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, dig into on...

You built the product. You know the problem. You know your solution works. So why should you have to be the one selling it? For many teacherpreneurs and education founders, the answer seems obvious: hire a salesperson, find a reseller, or bring in someone with the right connections to get your solution to schools. But there's a problem with handing off sales too soon. You may be trying to delegate something you haven't learned yet. In this episode of EdSales Edge, Josh Chernikoff, founder of ...

AI has made it faster than ever to find prospects, research school districts, write personalized emails, create LinkedIn messages, and build follow-up sequences. Education founders can now do in minutes what used to take hours. Yet many are still hearing the same thing: silence. The problem isn't AI. It's expecting AI to do the one job it was never meant to do—build relationships. In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, En...

Many teacherpreneurs and education founders work hard to build credibility. They earn certifications, highlight partnerships, showcase awards, and perfect their product. Yet sales conversations still stall. Buyers understand what they built, but never connect with why they built it. Without that connection, trust takes longer to build, sales conversations lose momentum, and revenue becomes harder to generate. In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Mac...

Every teacherpreneur and education founder starts with the same belief. If I create something that genuinely helps students, schools will want it. It sounds reasonable. But education businesses don't grow on value alone. They grow when buyers trust the founder, partners strengthen credibility, and the right people help create momentum around the solution. That's the real conversation in this episode. Originally recorded live at IFE in Monterrey, Mexico in April 2025, Josh Chernikoff, founder ...

Teacherpreneurs often believe growth will follow once they create something that works. It won't. A strong solution is the starting line, not the finish line. The hard part is figuring out who needs it, how to talk about it, and how to create demand around it. In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine (previously EdSales Elevation Experience) sits down with Grace Pokela, founder of The Lesson Laboratory. Grace built a digital curriculum and instr...

The school year may be ending, but the work of building a business doesn't stop. For teacherpreneurs, summer creates something rare: space. Space to think, plan, and improve the business while the pace of the school year slows down. But the lesson extends beyond teacherpreneurs. Every education business owner faces the same challenge: using quieter seasons to strengthen the business instead of simply reacting to it. In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales...

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 s...

A lot of education founders wear independence like a badge of honor. Figure it out yourself. Push through. Keep going. Until one day you're carrying every decision, every problem, and every hard conversation by yourself. That's usually when growth starts feeling heavier than it should. In this episode, Josh Chernikoff, founder of the EdSales Revenue Machine and John Gamba, Entrepreneur-in-Residence at Penn GSE talk about something most education founders underestimate: the impact of having th...

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 sp...

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 it inspired)—and why it matte...

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 ...

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 a...

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 d...

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 ...

“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 ...

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 y...

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...

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 22 guests. To thousa...

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...

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. ...

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 p...

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 fou...

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 b...

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 int...

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 desp...

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 l...

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 toda...

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 m...

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 eac...

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 educa...

What happens when you finally land the big meeting… and walk out with nothing but “We’ll think about it”? It’s the growth killer most founders don’t see coming—your pitch isn’t aligned with how education buyers actually make decisions. That’s why this live Breaking the Grade episode from ASU-GSV (the edtech conference each April in sunny San Diego) is such a win: I sat down with Paul Vallas——nationally recognized education leader, former superintendent of Chicago, Philadelphia, and New Orlean...

What if your biggest lead gen problem isn’t visibility — but the fact that your offer isn’t clear enough to close? Most EdTech founders think they have a marketing problem. Some think it’s a sales problem. But what they actually have is this: ❌ An offer that’s vague ❌ A proven model that’s undefined ❌ And no document that makes buyers say “yes” on the spot We first aired this episode on March 4, 2024 — and the response was so strong, we’re bringing it back. Because the Signature Solution isn’...

Most founders think their growth problem is sales. But Jolene Levin, entrepreneur, innovator and founder of NorvaNivel proved it’s the other way around: your sales reveal your growth problem. Jolene founded a classroom furniture company in Australia, scaled it across schools, and then brought it to the U.S. Three months after launching in the U.S., she closed $10M in deals. No sales team. No systems. No safety net. Just conviction, urgency—and operational chaos catching up fast. And two years...

Most EdTech demos fall flat because they focus on product—not pain. They walk through features—but skip the funding strategy. They sound polished—but feel disconnected. And when the call ends? No buy-in. No follow-up. No deal. That’s where John Gamba changes the game. John isn’t just an expert in EdTech innovation—he’s coached thousands of education entrepreneurs through founder-led sales. As Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, he’s helped founders...

What happens when your billion-dollar success story ends—and the market forgets your name? Robert Martellacci knows. And he didn’t quit—he reinvented. This episode isn’t just about resilience. It’s about the bold mindset shift it takes to reclaim relevance, rebuild trust, and restart traction when everything you built gets wiped off the board. Robert Martellacci—founder of MindShare Learning—joins me LIVE from the Education Research & Development Institute (ERDI), one of the most influent...

Here's the Messaging Fix You Didn’t Know You Needed If your EdTech offer sounds “nice” but never gets past your perfect client to respond… this episode is your wake-up call. Carlos Zapata, founder of Unicorn Academy, joins me live from the IFE Conference in Monterrey, Mexico — and pulls back the curtain on the exact moment his company stopped stalling and started closing. And here’s the kicker: it wasn’t the product that changed. It was the pitch. Carlos went from selling English upskilling a...

Let’s get one thing straight: September doesn’t start in September. It starts now—in June, July, and August. Because the biggest mistake founders make in summer isn’t taking a break. It’s confusing rest with silence. You can recharge and still generate leads. But most EdTech founders go dark. They hunker down. Rebuild ops. Tweak product. And completely disappear from LinkedIn. Then they roll into Q4 hoping “back to school” will bring the momentum. Spoiler: It won’t. In this episode of Breakin...

Most EdTech founders are still chasing views. Anissa Bouderraoui is closing pilots. She didn’t wait to go viral. She showed up consistently—with clarity, credibility, and the kind of messaging school leaders actually respond to. The result? No gimmicks. No funnels. Just a pipeline built on trust. Bolstered by LinkedIn consistency. 🎯 When Anissa started posting on LinkedIn, she wasn’t playing the influencer game. She was speaking directly to curriculum directors, bilingual program leads,...

Most education founders treat traction like a treadmill. When the leads slow down, they don’t stop to ask why—they sprint faster. More posts. More emails. More calls. More grind. But here’s what most founders miss: 📉 Motion ≠ Momentum 📉 Hustle ≠ Clarity 📉 Activity ≠ Conversion In this episode, Josh goes solo to unpack a hidden truth in EdTech sales: Your burnout might be bottlenecking your lead gen. He shares a real story from inside the EdSales Elevation Experience—Ken Spiegel, founder of Lo...

Most education companies don’t lose leads because their product is weak. They lose them because the message doesn’t land. They try to sound professional. Strategic. Smart. But polish ≠ presence. And clever ≠ clear. In this episode, Josh sits down with Mitch Weisburgh—a lifelong educator, EdTech veteran, and founder of MindShifting with Mitch—to unpack what really happens when education founders try to grow… without adjusting their communication to match their audience’s mindset. Mitch isn’t j...

Let’s start with a sitcom—and a truth bomb. In Seinfeld Season 5, Episode 22 ("The Opposite"), George Costanza hits rock bottom. No job. No love life. No confidence. So he flips the script. “If every instinct I have is wrong, then the opposite must be right.” And suddenly? He orders chicken salad instead of tuna. He tells the girl he’s unemployed and lives with his parents—and she’s into it. He lands a dream job with the New York Yankees. The world didn’t change. George did. Now, let’s ...

If you’re trying to grow your education business beyond where you started—this episode is for you. Because whether you’re moving from one country to another, or just one state to the next… The real challenge isn’t translation. It’s trust. In this episode of Breaking the Grade, I sit down with Denise Abulafia—EdTech founder, Penn GSE professor, and the visionary behind Educatina, a platform that scaled to over 6 million students in Latin America and earned traction across vastly different regi...

LinkedIn builds your credibility — Speaking amplifies it. In this episode of Breaking the Grade, I’m sharing how I went from avoiding stages entirely to speaking at in the last 13 months at Penn GSE, the University of Chicago, SXSW EDU, DC Startup Week, Education Research and Development Institute, XEdu, Institute for the Future of Education in Mexico, EdTech Institute of Chicago, and more. Not because I had the biggest platform—because I had the right message. Here’s the truth: I wasn’t afra...

You’re not afraid of hard work. You’ve put in the hours. You’ve sent the emails. You’ve done the demos. And still—no one’s biting. That was Ashton Tate. Founder of The Form Curriculum. Fitness coach-turned-EdTech founder. 500 cold calls deep… and still stuck. Then he changed one thing. He stopped selling—and started listening. In this episode of Breaking the Grade, Ashton shares the real story behind his pivot from “grinding” to getting real results—and how everything shifted when he joined t...

You think your sales process is tough? Try launching a brand new EdTech company during a global pandemic—while building trust with schools that aren’t exactly raising their hands. In this episode of Breaking the Grade, I sat down with Paul Moch, Founder of Camino 21 and now Vice Provost at Talisis, to break down what it really takes to build a scalable education business that gets acquired. Paul didn’t just build a product. He built trust. He didn’t guess what schools wanted. He asked. Listen...

You’re busy. But you’re not booked. You’re showing up on LinkedIn. You’re attending conferences. You’re tweaking your SEO. You’re following the playbook everyone told you to run. And still—your pipeline’s empty. In this episode of Breaking the Grade, Josh Chernikoff breaks down the silent mistake most education founders don’t realize they’re making: Mistaking motion for momentum. Mistaking activity for traction. Mistaking visibility for credibility.If you’re tired of doing everything “right” ...

Recorded live at IFE in Monterrey, Mexico, this episode features Beatriz Guillen, Executive Director at The Resource Foundation—a leader focused on strengthening education outcomes across Latin America. While her work centers on Latin America, the insights she shares here resonate globally—especially for education companies and founders navigating the U.S. market. This conversation is packed with real-world takeaways for education companies and founders navigating B2G, credibility-building, a...

Too many education founders build something incredible—only to realize they can’t sell it. They try to figure it out themselves… piecing together advice from free webinars, Twitter threads, and late-night YouTube binges. But without a proven system, the growth stalls—and burnout creeps in. In this episode of Breaking the Grade, I sit down with Nick Farrenkopf, CEO and founder of Wibly, who went from scrappy solo founder to sales-ready CEO. Nick didn’t come from a sales background—but when he ...

You’ve got the vision. The team. The momentum. So why does it feel like you’re sprinting on a treadmill with no finish line in sight? Here’s the truth: Most education companies don’t burn out because of a bad idea. They burn out because they’re trying to scale without a system. In this live episode of Breaking the Grade, recorded at IFE 2025 in Monterrey (Mexico), I sit down with Sergio Abramovich, CEO of Scala Learning, to unpack how fast-moving education companies can shift from burnout to ...

You’ve added decision-makers on LinkedIn. You’ve liked a few posts, maybe even commented. You’re showing up… but nothing’s turning into a call, let alone a contract. Sound familiar? That’s what I call the LinkedIn illusion—where activity feels like progress, but the results just aren’t showing up in your pipeline. Here’s the truth: If you're an education company trying to sell into institutions, LinkedIn isn’t about going viral. It’s about using consistency, clarity, and credibility to turn c...

Selling into education institutions—whether K–12 or higher ed—isn’t just about having a great product. It’s about understanding how those institutions work: how decisions are made, what roadblocks slow things down, and how to position yourself as a trusted partner—not just another vendor. In this special live episode recorded at IFE in Monterrey, Mexico, I sit down with Michael Fung, Executive Director of the Institute for the Future of Education at Tecnológico de Monterrey, to break down: Wh...

Does this sound familiar? You just spent thousands of dollars flying to ANOTHER education conference, setting up a booth, shaking hands with decision-makers. You collected a stack of business cards, had great conversations, and walked away thinking, this was a success. Two weeks later? It was the kiss of death for their conference strategy—no follow-ups turning into deals, no real sales pipeline, just a stack of business cards from people who seemed interested but have since disappeared. Her...

The education sector is buzzing with AI, but are schools and EdTech businesses truly leveraging it for sustainable growth? In this live episode, we cut through the hype to explore how AI, combined with strategic partnerships, can drive real impact. In this special live episode of Breaking the Grade, recorded LIVE from the IFE Conference in Monterrey, Mexico, I sat down with Jaime Pales, Co-Founder & President of Your Way Learning, and Michael Golden, Vice Dean of Innovative Programs &...

Summary When you're growing your education business, one big question always comes up—should you seek investment or bootstrap your way to success? In this episode, Josh Chernikoff breaks down the real challenges behind this decision. He shares lessons from his own journey, the mistakes founders make when chasing investment too soon, and what it really takes to build a business that attracts the right investors (if you even need them). We also get into smart ways to bootstrap, key signs that ...

Summary In this episode of Breaking the Grade, Josh Chernikoff tackles the big question: when’s the right time to bring on a sales team for your education-focused business? He shares why rushing to hire too soon can be a mistake and what you need to do first to make sure you're ready. Josh opens up about his own experiences, talking founder-led sales, how to refine your process, and the importance of building a strong foundation before scaling. If you're wondering how to grow your sales witho...

Summary In this episode of Breaking the Grade, I chat with Ernie, a seasoned leader who's been navigating the ever-changing education landscape since 2001. He shares valuable insights on how he completely transformed his sales system and unlocked 7-figures in proposals before the new school year started. Ernie shares all about staying adaptable, building relationships, and why rejection can be a powerful teacher. Together we dive into the unique challenges of selling in education, how networ...

Summary Nine years of building a business—and then, overnight, everything changes. Suddenly, you’re scrambling to keep things afloat, unsure of your next move. That’s exactly what happened to Matt Barinholtz, founder of Future Makers. When the pandemic hit in 2020, he had to pivot fast—shifting from offering services to selling products. The truth is, pandemic aside, business is always unpredictable—marketing trends shift, relationships fade as new players enter the scene, and sometimes, you...

Summary: In this episode of Breaking the Grade, Josh Chernikoff and Toni McMurray tackle the challenges of sales planning for education companies as the new year approaches. If you’re feeling overwhelmed by the tight sales window or struggling with staying top of mind with prospects, this episode is for you. We discuss the impact of inconsistent outreach and follow-ups, and how early planning and overcoming sales fears can set you up for success in 2025. Tune in to learn how to start building...

Summary: Sales in the education space can feel like an endless maze—long cycles, multiple decision-makers, and constant resistance. In this episode, Josh Chernikoff pulls back the curtain on the challenges EdTech founders face when selling to schools and districts. It’s not just about getting through the door; it’s about navigating complex decision-making processes and staying persistent when things don’t move as quickly as you'd like. If you’re feeling stuck or frustrated by slow progress a...

Summary: Wondering when you should really start selling in the education market? In this episode, Josh Chernikoff dives into the right timing and approach for effective sales in the education space. Spoiler: it’s not just about waiting until you have a perfect offer. It’s about understanding the specific buying cycles and decision-making processes that are unique to educational institutions. Josh breaks down why timing is key—and how positioning yourself early can build valuable relationshi...

Summary: Are your sales calls feeling like one-way pitches instead of real conversations? In this episode, Josh Chernikoff uncovers a simple yet powerful shift that could change how you approach every sales call moving forward. Spoiler: it’s not about selling harder or pushing your offer more aggressively. It’s about tapping into a skill most salespeople overlook. Josh dives deep into how listening can transform your calls, build trust, and help you uncover your prospects' true needs—without ...

Summary: Selling to schools and districts is more than just having a good product—it’s about really understanding the specific challenges and needs of the education market. In this episode, Special Guest: John Gamba (Entrepreneur in Residence at the University of Pennsylvania Graduate School of Education) and I talk about how to deliver better sales demos, especially when technical issues or multiple decision-makers are involved. From using Loom videos to keep the conversation going bet...

Join me as I sit down with Chris and Corey from Rocket PD to talk about how they revamped their entire sales process to feel more natural and focused on building relationships with their ideal customers. Chris and Cory have years of SaaS experience under their belt and they know a lot about marketing and selling software, but selling to schools felt like a whole different ball game. And so we worked on building out their sales process together to fit them, their business and their clients. If...

Summary Imagine a tool that could revolutionize how students manage their homework—built not by some big tech company, but by a parent and a 12-year-old visionary. Curious? In this episode, we're diving into a startup story that's as unique as it gets. A co-founder whose biggest challenge wasn’t just building the tech but navigating the labyrinth of the education market... Join me as I interview Brent Newton, founder of MyOwl, about the challenges he and his daughter faced in getting...

Summary: Starting a business with the goal of solving complex educational problems is a tall order. But Sam Saarinen, founder and CEO of Edapt Technologies, embraced this challenge head-on. In this episode, Sam shares his entrepreneurial journey—one marked by ambitious starts, hard-learned lessons, and a game-changing pivot that led to remarkable business growth. If you’re an entrepreneur struggling to find your footing, this episode is packed with actionable insights on refining your product...

In this episode, Josh Chernikoff discusses the importance of implementing systems in order to scale and grow an education business. He highlights three powerful systems: offer system, lead generation and sales system, and delivery system. He emphasizes the need for a repeatable and scalable offer, a lead generation system to attract and nurture ideal clients, and a delivery system to ensure client success. Josh also acknowledges that there will be glitches and mistakes along the way, but it's...

In this episode, Josh Chernikoff shares his experiences and challenges in growing his second business, Flex Academies. He discusses the importance of finding the ideal client, pivoting the business model, and building a strong offer. He also emphasizes the need for a lead generation system and the importance of surrounding oneself with experts. Josh highlights the significance of systems in scaling a business and shares his own journey of continuous learning and improvement. Takeaways: Find...

In this conversation, Josh Chernikoff interviews Kathryn Adabonyan, the founder and CEO of Go Pursue, a company that helps high school students explore career options and connect with professionals in those fields. They delve into Kathryn's journey as an entrepreneur, a testament to her resilience in overcoming sales and marketing challenges. Kathryn shares how the EdSales Elevation Experience helped her reframe her mindset about LinkedIn and establish herself as a thought leader in her indus...

In this conversation, Josh Chernikoff discusses his nine-step process for building lead generation machines that produce high-quality and high-converting leads on repeat. He addresses the common challenge of not knowing how to get leads and emphasizes the importance of founder-led sales. Josh shares his own experience of starting a tutoring business without any sales experience and explains how he overcame obstacles to become successful. He breaks down each step of his process, including gett...

Don’t miss the Catalyst at Penn GSE Innovation Summit on June 21st at the University of Pennsylvania. It’s a must-attend event for entrepreneurs in the education sector, filled with insights on advancing your business. Register now at https://mailchi.mp/gse.upenn.edu/catalyst-summit-2024 Rose, a successful entrepreneur and educator, shares her experience with the Ed Sales Elevation Experience. She discusses the challenges she faced in growing her business in education and how the program hel...

Don’t miss the Catalyst at Penn GSE Innovation Summit on June 21st at the University of Pennsylvania. It’s a must-attend event for entrepreneurs in the education sector, filled with insights on advancing your business. Register now at https://mailchi.mp/gse.upenn.edu/catalyst-summit-2024 Welcome to today’s episode where we delve into the world of lead generation within the education industry. We'll explore a variety of strategies from quick social media ads to the slow and steady wins of SEO...

In this episode, Josh discusses the importance of identifying the main stakeholders in the education space and how to sell to them effectively. He shares case studies of Brent and Katherine, who faced the challenge of determining who to sell to and how they overcame it. Josh emphasizes the need to focus on the benefits and transformation your solution can provide to the main stakeholder while also considering the benefits for other stakeholders. He also mentions the EdSales Elevation Experien...