From Stuck Deals to Simple Wins: How to make education buyers say yes

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 [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Elevation Experience [https://www.linkedin.com/company/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 [https://www.linkedin.com/in/johngamba], Entrepreneur-in-Residence at Penn GSE, joins on his birthday on Wednesday for a breakdown of Moneyball [https://www.rottentomatoes.com/m/moneyball] by Michael Lewis [https://michaellewiswrites.com/] (and the film it inspired)—and why it matters for every education founder.  They explore why the smartest founders stop chasing flashy opportunities and start building proof that compounds over time. Winning companies don’t outspend everyone. They find overlooked opportunities—and let proof do the work. This episode is about sales strategy—but also resilience, entrepreneurship, recovery, and staying in the game long enough to win. WHY THIS MATTERS Too many education founders are trying to hit home runs before they’ve proven they can consistently get on base. They chase: * giant districts * conference hype * vanity metrics * long-shot opportunities * buyers with no urgency Meanwhile, the best founders focus on: * implementation * speed * relationships * feedback * proof of effectiveness * repeatable outcomes John references his favorite line from Moneyball that captures the entire philosophy: “We pay you to get on first, not to get thrown out at second.” It is a reminder that sustainable growth doesn’t come from chasing home runs—it comes from building proof, stacking small wins, and creating momentum that compounds over time.. KEY STRATEGIES & MENTAL MODELS 1️⃣ Small Districts Are Not Small Opportunities Smaller districts often provide faster decisions, stronger access, and quicker implementation cycles than massive systems. 2️⃣ Proof Compounds The most valuable thing an early-stage company can build is evidence that the solution works. Not hype. Not impressions. Proof. 3️⃣ Compress Contact-to-Contract Founders waste years chasing deals that never move. Momentum comes from shortening the distance between conversation and implementation. 4️⃣ Clarity Beats Flash Conference buzz and “interesting conversations” don’t build businesses. Urgency, fit, timing, and measurable outcomes do. 5️⃣ Winning Isn’t Always Loud Sometimes winning is: * showing up * recovering * learning * improving * staying in the game long enough for the proof to compound WHO THIS EPISODE IS FOR * Founders chasing big districts but struggling to close * Early-stage EdTech companies under $2M ARR * Sellers confusing pipeline activity with traction * Entrepreneurs feeling pressure to “look bigger” NEXT STEP Before chasing your next “huge opportunity,” ask yourself: Do we actually have proof this works consistently yet? The best founders find overlooked value, build proof, and let it compound. Text “TARGETING” to 771-333-4233 🔁 SUBSCRIBE & SHARE Follow EdSales Edge and share this with a founder who keeps chasing home runs… …when the real breakthrough is learning how to consistently get on base. Connect with Josh Chernikoff Founder, Edsales Elevation Experience Host, Edsales Edge Show 🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/ [https://www.linkedin.com/in/joshuachernikoff/] 📘 Facebook: https://www.facebook.com/joshua.chernikoff [https://www.facebook.com/joshua.chernikoff] 📸 Instagram: https://www.instagram.com/joshuadcdc/ [https://www.instagram.com/joshuadcdc/] 📩 Email: Jc@joshchernikoff.com [Jc@joshchernikoff.com] Join the Edsales Entourage Get closer to the conversations, strategies, and operators inside the ecosystem: 👉 https://www.skool.com/entourage [https://www.skool.com/entourage]

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 [https://www.michaellewiswrites.com/#top] 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 [https://www.linkedin.com/in/billy-bean-90594735], 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, and more conversations. But the best founders don’t grow by chasing more. They grow by mining deeper inside the right opportunities already around them. In this episode of EdSales Edge, Josh Chernikoff [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Elevation Experience [https://www.linkedin.com/company/edsales-elevation-experience] breaks down how education founders can apply the Moneyball mindset to uncover hidden revenue inside their pipeline, relationships, and existing conversations. Using examples from leaders like Brooke Olsen-Farrell [https://www.linkedin.com/in/brooke-olsen-farrell-1837a953], Wayne Bovier [https://www.linkedin.com/in/waynebovier], Paul King [https://www.linkedin.com/in/paul-king-30b0ab96], Rose Hastreiter [https://ca.linkedin.com/in/rhastreiter], and Kathryn Adabonyan [https://www.linkedin.com/in/k-adabonyan], Josh explains why smaller, overlooked opportunities often create more momentum than the obvious “big wins” founders chase. Also—after being on the injured list following triple bypass surgery, Josh is stepping up to the plate again. Thank you for all the support and well wishes. This episode is about learning how to recognize hidden value before everyone else does. WHY THIS MATTERS Most pipelines don’t fail from lack of leads. They fail from lack of clarity. Founders confuse activity with momentum: more emails, more calls, more outreach. But real growth comes from seeing where revenue already exists. This episode is for founders stuck chasing leads with no traction, busy pipelines that don’t convert, and teams struggling to recognize real opportunities before everyone else does. KEY STRATEGIES & MENTAL MODELS 1️⃣ Stop Resetting. Go Deeper Most founders leave opportunities too early. Top sellers revisit conversations and environments until real revenue shows up. 2️⃣ Mining Beats Hustling Amateurs chase everywhere. Pros look for patterns before they act. Better targeting = better pipelines. 3️⃣ Signal vs. Noise Not every “interest” matters. Mining means knowing what actually converts into revenue. 4️⃣ Pattern Recognition Is the Edge Billy Beane didn’t win with more players. He won by knowing what signals mattered—and acting on them. NEXT STEP Before you chase more leads, ask: Am I missing revenue already inside my pipeline? Text “TARGETING” to 771-333-4233 for the framework to see opportunities more clearly. 🔁 SUBSCRIBE & SHARE Follow EdSales Edge and share this with someone still chasing more leads… when the real win is learning how to mine the revenue already in front of them. Connect with Josh Chernikoff Founder, Edsales Elevation Experience Host, Edsales Edge Show 🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/ [https://www.linkedin.com/in/joshuachernikoff/] 📘 Facebook: https://www.facebook.com/joshua.chernikoff [https://www.facebook.com/joshua.chernikoff] 📸 Instagram: https://www.instagram.com/joshuadcdc/ [https://www.instagram.com/joshuadcdc/] 📩 Email: Jc@joshchernikoff.com [Jc@joshchernikoff.com] Join the Edsales Entourage Get closer to the conversations, strategies, and operators inside the ecosystem: 👉 https://www.skool.com/entourage [https://www.skool.com/entourage]

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 [https://www.linkedin.com/in/johngamba], Entrepreneur-in-Residence at Penn GSE, steps in at the wheel as Josh Chernikoff [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Elevation Experience [https://www.linkedin.com/company/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 [https://www.linkedin.com/in/celinex7766], founder of AskSia [https://www.linkedin.com/company/asksia-inc], an AI-powered learning platform serving over 2 million users across 120+ countries, the conversation dives deep into the real driver of growth: targeting. They break down how AskSia went from almost no traction to global scale—not by expanding faster, but by narrowing sharper. From high-stakes learners to international expansion, John and Celine unpack why growth doesn’t come from reaching more people—it comes from reaching the right people. If growth feels inconsistent, this episode will make it obvious why. WHY THIS MATTERS This isn’t just a startup story—it’s a targeting lesson most education founders need right now. Many founders think growth comes from: More content. More ads. More visibility. But growth starts with clarity. When targeting is unclear: • Messaging stretches • Conversion drops • Growth depends on luck When targeting is sharp: • Users understand faster • Adoption feels easier AskSia accelerated once the audience became clear. Not because the product changed. Because the targeting did. KEY STRATEGIES & MENTAL MODELS 1️⃣ Urgent Users Drive Early Growth Start with people who deeply need the solution. 2️⃣ Build Inside Familiar Markets Early traction came from a market they understood well. 3️⃣ Narrow Beats Broad Focused segments create faster adoption than wide reach. 4️⃣ Local Context Matters Global expansion only worked with cultural understanding. 5️⃣ Systems Beat Virality Social spikes fade. SEO and AI indexing create consistency. WHO THIS EPISODE IS FOR • Founders struggling to convert attention into users • Teams targeting too many audiences • Builders with unclear positioning • Anyone fixing marketing instead of targeting NEXT STEP Before your next growth decision, ask: Are we chasing more people… or finally targeting the right people? Because targeting clarity turns effort into scale. Text “TARGETING” to 771-333-4233 SUBSCRIBE & SHARE Follow EdSales Edge and share this with someone trying to grow faster… …when the real unlock is better focus, not more reach. Connect with Josh Chernikoff Founder, Edsales Elevation Experience Host, Edsales Edge Show 🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/ [https://www.linkedin.com/in/joshuachernikoff/] 📘 Facebook: https://www.facebook.com/joshua.chernikoff [https://www.facebook.com/joshua.chernikoff] 📸 Instagram: https://www.instagram.com/joshuadcdc/ [https://www.instagram.com/joshuadcdc/] 📩 Email: Jc@joshchernikoff.com [Jc@joshchernikoff.com] Join the Edsales Entourage Get closer to the conversations, strategies, and operators inside the ecosystem: 👉 https://www.skool.com/entourage [https://www.skool.com/entourage]

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 [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Elevation Experience [https://www.linkedin.com/company/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 what fits his circle of competence. Saying yes to every school, every district, every “maybe” conversation doesn’t build momentum, it creates noise. Like Buffett avoiding investments he can’t understand, you should avoid opportunities you can’t predict. Because clarity—not volume—drives growth. WHY THIS MATTERS Here’s the part no one says: You can be working hard… and still going the wrong way. In education sales, activity looks like progress, until it doesn’t. If your buyers don’t already value what you do, everything feels heavy. Deals drag, conversations stall, and nothing really moves. When targeting is off, it’s hard. When it’s right, things click, faster decisions, easier conversations, a pipeline that actually makes sense.  KEY STRATEGIES & MENTAL MODELS 1️⃣ Stop Chasing “Potential” Just because something could work doesn’t mean it will. Look for alignment, not possibility. 2️⃣ Know Where You Actually Win Your best opportunities aren’t everywhere, they’re specific. Pay attention to where things have worked before. 3️⃣ Choose Clean Windows The best clients already believe in the outcome. You’re not convincing, you’re stepping into something that already exists. 4️⃣ Give Yourself Permission to Say No Every “yes” to the wrong opportunity slows you down. Filtering is what creates focus. 5️⃣ Look for Patterns, Not Random Wins The goal isn’t one good deal, it’s repeatable success. Find the environments where things consistently work. WHO THIS EPISODE IS FOR If you’ve ever thought: * “I have a lot of conversations, but nothing closes” * “My pipeline looks full, but it doesn’t feel strong” * “I don’t know which opportunities are actually worth it” This episode is for you. NEXT STEP Before you send your next message or book your next call, pause and ask: * Does this person already value what I do? * Do I understand how decisions happen here? * Or am I just hoping this turns into something? That one shift—from hoping to knowing—changes everything. If you want help getting that clarity, text “TARGETING” to 771-333-4233 🔁 SUBSCRIBE & SHARE If this episode made you rethink how you approach your pipeline, share it with someone who’s been working hard, but not seeing results. Connect with Josh Chernikoff Founder, Edsales Elevation Experience Host, Edsales Edge Show 🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/ [https://www.linkedin.com/in/joshuachernikoff/] 📘 Facebook: https://www.facebook.com/joshua.chernikoff [https://www.facebook.com/joshua.chernikoff] 📸 Instagram: https://www.instagram.com/joshuadcdc/ [https://www.instagram.com/joshuadcdc/] 📩 Email: Jc@joshchernikoff.com [Jc@joshchernikoff.com] Join the Edsales Entourage Get closer to the conversations, strategies, and operators inside the ecosystem: 👉 https://www.skool.com/entourage [https://www.skool.com/entourage]

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 [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Elevation Experience [https://www.linkedin.com/company/edsales-elevation-experience] and John Gamba [https://www.linkedin.com/in/johngamba], 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 creates confusion. Josh and John unpack how education buyers think, why “vitamins” don’t get funded, and how to position your solution as a true “painkiller” tied to real priorities. They also show why safety wins—and how pilots, proof, and clear outcomes beat polished pitches every time. If your deals feel stuck, the problem isn’t effort. It’s your offer. WHY THIS MATTERS In education, buyers aren’t just choosing a product—they’re managing risk. They’re thinking about: * Internal pushback * Budget constraints * Reputation with leadership and boards * Whether this will actually work When your offer feels complicated, unclear, or too broad, it increases perceived risk. And when risk goes up—decisions slow down or stop entirely. Simple, focused offers feel safer. And safer offers move faster. KEY STRATEGIES & MENTAL MODELS 1️⃣ Less Is More (The Offer Paradox) Adding more services, features, or flexibility weakens your offer. Clarity—not quantity—drives decisions. 2️⃣ Painkillers vs. Vitamins If your solution isn’t tied to a top institutional priority, it won’t get funded. Solve urgent pain—not “nice-to-have” improvements. 3️⃣ One Offer. One Transformation. Strong offers focus on a single, clear outcome for a specific buyer. Anything more creates confusion. 4️⃣ Safety Sells (SPP Framework) * Story → Show you understand the problem * Proven → Demonstrate measurable results * Precedent → Show repeatable success Buyers move when they feel safe—not when they’re impressed. 5️⃣ Clarity Over Customization Customization feels helpful—but it turns your offer into a menu. Menus create hesitation. Clear offers create action. WHO THIS EPISODE IS FOR * Founders adding more services but seeing fewer decisions * Sellers dealing with long, stalled sales cycles * Education entrepreneurs struggling to position their value * Anyone hearing “this is interesting” but not getting a yes NEXT STEP Before your next conversation, ask yourself: Is my offer simple enough to understand in one sentence—and strong enough to solve a real, urgent problem? If not, don’t add more. Strip it down. Text “SOLUTION” to 771-333-4233 Join: Skool.com/entourage Connect with Josh Chernikoff Founder, Edsales Elevation Experience Host, Edsales Edge Show 🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/ [https://www.linkedin.com/in/joshuachernikoff/] 📘 Facebook: https://www.facebook.com/joshua.chernikoff [https://www.facebook.com/joshua.chernikoff] 📸 Instagram: https://www.instagram.com/joshuadcdc/ [https://www.instagram.com/joshuadcdc/] 📩 Email: Jc@joshchernikoff.com [Jc@joshchernikoff.com] Join the Edsales Entourage Get closer to the conversations, strategies, and operators inside the ecosystem: 👉 https://www.skool.com/entourage [https://www.skool.com/entourage]