Stop Pitching: What Actually Gets a Superintendent’s Attention

The Summer Advantage: What Teacherpreneurs Should Build Before Fall

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 [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Revenue Machine, and John Gamba [https://www.linkedin.com/in/johngamba], Entrepreneur-in-Residence at Penn GSE, discuss why summer is one of the most important seasons for teacherpreneurs. Not because schools are buying more, but because founders finally have space to think, plan, refine, and prepare for what's next. The conversation explores common mistakes: forcing offers that no longer match buyer behavior, disappearing completely, or staying trapped in delivery work without improving the business itself. Josh and John share a practical framework for using summer intentionally. From clarifying offers and understanding buyer priorities to creating a focused 90-day plan, this conversation is about building a stronger fall before it arrives. WHY THIS MATTERS Growth problems don’t start when sales slow down. They start when founders stop checking what’s actually working. Most education businesses enter a new school year carrying the same problems: unclear messaging, weak positioning, inconsistent outreach, and broken sales flow. Summer is the window to fix it—before those issues get expensive. The founders who grow aren’t always the busiest. They’re the ones who use quiet seasons to sharpen their message, deepen relationships, and prepare for the next buying cycle. KEY STRATEGIES & MENTAL MODELS 1️⃣ Sell Where Demand Is Real Focus on buyers already showing interest instead of forcing conversations that aren't moving. 2️⃣ Clarify the Transformation Be able to explain who you help, how you help, and what outcome you create. If buyers can't repeat it back, your message isn't clear enough. 3️⃣ Build a 90-Day Plan Skip the giant annual strategy document. Focus on the next ninety days. Clear priorities create momentum. 4️⃣ Work on the Business Use summer to refine your offer, strengthen outreach, revisit goals, and prepare for the next selling season. 5️⃣ Understand What Buyers Care About Strong founders focus on the problems buyers are actively trying to solve. Summer is a great time to do that research. WHO THIS EPISODE IS FOR * Teacherpreneurs building education businesses * Educators turning classroom expertise into a business * Founders struggling with sales consistency * Operators building repeatable growth systems 🚀 NEXT STEP Ask yourself: If the fall started tomorrow, would your business be ready? The next season is built before it arrives. Text "90 DAYS" to 771-333-4233 Get the 90-Day Founder Challenge—a practical framework for your next 90 days. Teacher-founders: limited 1:1 planning sessions available. 🔁 SUBSCRIBE & SHARE Follow EdSales Edge and share this with a founder who plans to "figure it out" in September. The next school year gets built long before the first day of school. 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 Pitching: What Actually Gets a Superintendent’s Attention

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 [https://www.linkedin.com/in/jtbloom] 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 [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Revenue Machine sits down with Jared for an unusually honest conversation about what actually gets a superintendent's attention—and why most education sales outreach misses the mark. Jared explains why cold emails rarely stand out, why generic LinkedIn pitches feel transactional, and what separates a vendor from a true partner. He also shares how districts evaluate new solutions and why some companies earn long-term trust while others never make it past the first conversation. For founders, sales teams, and customer success leaders, this episode offers a rare opportunity to hear directly from the other side of the table. WHY THIS MATTERS Most education companies assume they have an outreach problem. In reality, many have a trust problem. When relationships are weak: * Every sales conversation feels harder * Follow-up becomes chasing * Pilots stall * Adoption slows When trust exists: * Conversations happen faster * Feedback becomes honest * Internal champions emerge * Partnerships last longer The strongest education sales strategies aren't built around volume. They're built around credibility. KEY STRATEGIES & MENTAL MODELS 1️⃣ Relationships Scale Better Than Outreach The goal isn't more conversations. The goal is stronger conversations with the right people. 2️⃣ Relationships Are Built In Real Conversations Face-to-face interactions allow education leaders to understand who they're working with—not just what they're buying. 3️⃣ Start Small, Then Expand Successful districts start with small pilots, gather evidence, and expand only after results are visible. 4️⃣ Teacher Buy-In Matters Even the strongest product can fail if the people using it don't believe in it. 5️⃣ Partnership Continues After The Sale The most successful companies stay involved, listen closely, and adapt based on district feedback. WHO THIS EPISODE IS FOR * Education founders struggling to break into districts * EdTech sales teams relying heavily on cold outreach * Customer success leaders focused on retention and adoption * Companies looking to build long-term district partnerships * Anyone selling into K-12 education 🚀 NEXT STEP Ask yourself: Are you spending more time increasing outreach... or increasing trust? Because schools rarely buy from strangers. They buy from partners. Text "RELATIONSHIP" to 771-333-4233. 🔁 SUBSCRIBE & SHARE Follow EdSales Edge and share this with someone who thinks more outreach is the answer. Sometimes the real answer is building better relationships. 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 Building Alone: Why Community Changes Everything

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 [https://www.linkedin.com/in/joshuachernikoff], founder of the EdSales Revenue Machine and John Gamba [https://www.linkedin.com/in/johngamba], Entrepreneur-in-Residence at Penn GSE talk about something most education founders underestimate: the impact of having the right people around you. Not a bigger network. Not another Slack group you'll never open. Real relationships with people who can challenge your thinking, share what they've learned, and help you see around corners. Drawing from their own experiences building companies, founder communities, and entrepreneurial programs, Josh and John explore why so many founders in the education space try to build alone—and what changes when they stop. One of the most powerful ideas in this conversation comes from Theo of Golden, the bestselling novel by Allen Levi [https://www.allenlevi.com/]—what he calls a murmuration. A flock of birds moving together as one. No single leader. No one carrying the weight alone. Just shared direction, shared motion, shared awareness. It’s a simple image—but it reframes everything about how founders think about growth. Because most people are still trying to be the one bird doing everything alone. WHY THIS MATTERS Building a business is already heavy. But doing it alone changes the weight completely. It slows your thinking, limits your perspective, and makes every decision feel bigger than it should. Most education founders don’t need more effort. They need better proximity—to people who’ve already seen what they’re trying to figure out. That’s what community actually solves. KEY STRATEGIES & MENTAL MODELS 1️⃣ Community Is a Growth Asset Strong communities create faster learning, better feedback, and stronger execution. 2️⃣ Stop Being the Bottleneck Whether you're building an EdTech product or leading education sales, growth gets harder when every answer depends on you. 3️⃣ Borrow Expertise You don't need every skill. You need access to people who bring different perspectives. 4️⃣ Vulnerability Builds Trust The most valuable founder conversations usually start with honesty, not expertise. 5️⃣ Momentum Is Collective Growth compounds faster when people move together than when everyone moves alone. 🎯 WHO THIS EPISODE IS FOR * Education founders carrying too much themselves * EdTech leaders building in isolation * Education sales teams stuck in growth plateaus * Operators seeking stronger accountability. 🚀 NEXT STEP Ask yourself: Where are you trying to grow alone when the right community could help you move faster? Community isn't a support system. It's infrastructure. Text "COMMUNITY" to 771-333-4233. 🔁 SUBSCRIBE & SHARE Follow EdSales Edge and share this with a founder in the education industry who feels like they have to carry everything alone... ...because growth gets easier when you stop building by yourself. 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]

The Clarity That Came After the Pause: A Triple Bypass, a Forced Stop, and a Fresh Start for My Business.

Every education founder eventually hits a point where their sales system has to evolve. For Josh Chernikoff [https://www.linkedin.com/in/joshuachernikoff], 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 does not fix a broken or immature sales system. In many cases, it just exposes the friction already there. Unclear positioning. Slow follow-up. Messy pipelines. Conversations that stall for reasons no one can explain. That friction is what quietly drains founders. Inside the new system, Josh walks through the 3E Method — Evaluate, Elevate, Engine — designed to move founders out of confusion and into execution. Not learning more. Building faster. At its core, this episode is about replacing business drag with repeatable movement. If you’re building an education business that needs to grow without constant strain, this episode shows what has to change first. WHY THIS MATTERS A lot of founders are carrying systems that quietly exhaust them. Unclear positioning creates longer sales cycles. Weak follow-up creates stalled conversations. Undefined buyers create heavier messaging and more complicated offers. The business keeps moving. But it does not actually get lighter. That is the danger. Founders normalize friction for so long that they start treating exhaustion like maturity. This episode challenges that completely. 🔑 KEY STRATEGIES & MENTAL MODELS 1️⃣ Motion Can Hide the Real Problem More activity often delays the harder strategic decisions. Busy founders can still be avoiding clarity. 2️⃣ Clarity Reduces Friction The faster buyers understand the problem, the safer the next step feels. Especially in education. 3️⃣ Systems Should Create Relief A business should not become heavier every time demand increases. Strong systems reduce operational drag. 4️⃣ Support Matters Between Decisions Most founders do not get stuck during inspiration. They get stuck during implementation. 🎯 WHO THIS EPISODE IS FOR * Founders exhausted by constant operational weight * Education companies stuck in unclear positioning * Teams confusing motion with momentum * Operators trying to build cleaner revenue systems 🚀 NEXT STEP Ask yourself: Where has your business become heavier than it needs to be? Growth should not depend on constant strain. Text “REVENUE” to 771-333-4233 to learn more about the EdSales Revenue Machine. 🔁 SUBSCRIBE & SHARE The strongest businesses are not always the busiest. They are the clearest. 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]

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]