Breaking the Grade

Josh Chernikoff

Breaking the Grade is a thought-provoking podcast that follows entrepreneurs in the education space as they make their way to the top. Tune in for stories about breaking norms, introducing new ideas, and shaping our future society through every lesson let out.

  1. The Guarantee Shift: Karim Kuperhause on How Education Founders Build Trust and Win Qualified Leads Without Sounding Desperate

    1天前

    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 down with Karim Kuperhause— former teacher, founder of 3 tutoring centers + 32 satellite programs, and now CEO of HierSales, the company helping education organizations build outcome-based guarantees that change the game. Karim isn’t just talking theory. He’s building the future. Because the future of education sales—from classrooms to campuses—is guarantees. Superintendents, districts, universities, and decision-makers at every level won’t keep gambling on “maybe.” They want confidence. They want results. They want partners willing to shift the risk. And guarantees are how you deliver it. 🔑 5 Big Takeaways for Education Founders 1️⃣ Why Founders Lose Deals They Could Win Ducking the “failure” question signals you don’t believe in your own product. 2️⃣ The 3-Part Framework for Guarantees Outcome. Timeline. Safeguard. Build these in, and you win trust before you pitch. 3️⃣ Why Pilots Build Trust Faster Than Promises Districts are risk-averse. A low-cost pilot proves you work and builds confidence without big commitments. 4️⃣ Guarantees Double as a Client Filter A strong guarantee doesn’t just attract buyers—it shows you who’s serious. If they won’t even test, they’re not your client. 5️⃣ Why Guarantees Beat Demos Demos impress no one. Outcomes and guarantees close deals. If your deals keep stalling at “interested” but never closing, this is your wake-up call. Guarantees aren’t optional—they’re the future of selling in education. 📩 DM me “Guarantee” and I’ll show you how to structure offers that build trust and filter perfect-fit clients. 📤 Know a founder still hiding behind buzzwords instead of outcomes? Send them this episode—it might save them from losing their next big deal. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more founders can close bigger, better deals. #EducationSales #FounderSales #MessagingStrategy #HigherEd #K12 #BreakingTheGrade #ClarityConverts #GrowthStrategy #KarimKuperhause #HierSales

    45 分钟
  2. From Invisible to Irresistible: Michael Campbell on Using Research and Proof to Build Trust, Generate Leads, and Drive Education Growth

    9月7日

    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 sales stalls early growth—and how the smartest founders turn research studies, customer listening, and evidence-backed storytelling into trust that fills their funnels and converts prospects into paying clients. 💡 He even gets into hard numbers: why a $20K–$30K university research study might be the best marketing investment you’ll ever make—and how to turn it into white papers, videos, and proof points that fuel your pipeline. If you’re tired of stalled pitches and sales hires that underperform, this episode is your blueprint for turning evidence into revenue, trust, and consistent leads. 🔑 5 Big Takeaways for Education Founders 1️⃣ Invest in Evidence Invest in a structured research study to prove your solution works. Turn the results into white papers, videos, and other assets that double as lead-generation tools. 2️⃣ Proof = Pipeline Case studies, pilots, and research-backed evidence create credibility that fuels conversations, earns trust, and gets buyers to say yes. 3️⃣ Sales Isn’t Your First Hire Hiring a teacher or untested salesperson won’t magically create revenue. Validate your market and build proof first. 4️⃣ Slow Sales = Smart Sales in Education One-call closes are rare. Trust, referrals, and relationships are your real growth multipliers. 5️⃣ Courage + Consistency = Contracts Most founders quit before traction. Those who stick with research, realistic goals, and customer listening win contracts and sustainable growth. 📩Want to flip research into a repeatable lead-generation engine? DM me “Lead Gen” and I’ll walk you through the exact framework we use to help founders turn proof points into paying customers. 📤 Know an EdTech founder struggling to turn their proof into pipeline? Send them this episode—they’ll thank you later. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education leaders can turn research, credibility, and proof into measurable growth and leads. #EdTech #FounderSales #LeadGeneration #EdSales #EducationInnovation #ASUGSV #BreakingTheGrade #GrowthStrategy

    29 分钟
  3. $9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore

    8月31日

    $9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore

    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 educator training and AI-driven learning models— and Michael Golden, Vice Dean of Innovative Programs and Partnerships and Executive Director of Catalyst at Penn GSE and ex-Microsoft exec At the time, YourWay was still early—focused on building with intention, grounding in research, and designing tools teachers would actually use. Fast forward: they’ve raised $9 million and launched a partnership with Penn GSE turning credibility and strategic alignment into a pipeline of opportunities. This episode takes you back to that conversation—before the headlines—showing how YourWay built the foundation that turned momentum into investments and qualified leads. 5 Big Takeaways for Education Founders 1️⃣ AI Isn’t the Differentiator—Your Approach Is Buzzwords don’t close deals. Clear, outcome-driven solutions do and they attract schools, districts, and buyers actively looking to invest. 2️⃣ Research to Practice = Credibility Buyers don’t want “feel good” workshops. They want evidence your AI or EdTech solution drives measurable classroom impact—your strongest lead-generation tool. 3️⃣ Your DNA as a Founder Matters Persistence, humility, and community separate ventures that scale from those that fade—especially in the long sales cycles of education. 4️⃣ Partnerships Trump Solo Play The fastest path to traction is aligning with research institutions, accelerators, and trusted partners who validate your model—and bring you in front of qualified buyers. 5️⃣ Mission + AI + Partnerships = Long-Term Wins Quick cash grabs don’t last. Buyers back founders who balance innovation with credibility and sustainability.  YourWay’s story proves that when vision, credibility, and timing align, momentum turns into millions. The lesson is clear: lead with outcomes, use AI with intention, and anchor growth in partnerships that last. 📩 DM me “Momentum” and I’ll show you how to structure your growth story so buyers and investors notice—and respond. 📤 Know a founder chasing buyers with AI hype but no real partnerships? Send them this episode. It might save them from losing deals before they scale. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education founders can turn AI innovation + strong partnerships into consistent sales growth. #EdTechSales #FounderLedGrowth #AIinEducation #PartnershipsThatScale #ResearchToPractice #SalesStrategy #GrowthStrategy #BreakingTheGrade #EdSales

    27 分钟
  4. From “Great Pitch” to Signed Contract: Paul Vallas on the Buyer’s Lens That Closes Education Deals

    8月24日

    From “Great Pitch” to Signed Contract: Paul Vallas on the Buyer’s Lens That Closes Education Deals

    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 Orleans, CEO of the Recovery School District after Hurricane Katrina, and co-founder of both Vallas Group Inc. and Global Educator And here’s why his perspective can change your sales game: ✅ He’s overseen multi-billion-dollar budgets and made the final call on which solutions get funded. ✅ He’s rebuilt entire school systems in crisis and driven record student gains in districts with 80%+ poverty rates. ✅ He’s been pitched thousands of times—and knows exactly why most vendors fail. And here’s the kicker: Paul isn’t just sharing his story. He’s pulling back the curtain on the decision-making framework education buyers actually use before they say “yes.” If you’re chasing deals in the education market, this conversation shows you how to go from “great product” to “signed contract.” 5 Big Takeaways for Education Founders 1️⃣ The 3-Point Test Every Buyer Uses Quality, fit, scalability—miss one, and the deal dies. Know where you stand before you pitch. 2️⃣ The Core Priorities Every Buyer Protects Every buyer looks for certain fundamentals—curriculum strength, data use, interventions, support, time on task. Tie your solution directly to these. 3️⃣ Why Misaligned Products Get Cut First Misaligned programs are the first to go in a budget cut. Position yourself as mission-critical, not optional. 4️⃣ How to Make Your Offer Budget-Proof Solutions tied to measurable outcomes survive funding shifts. Prove your link to results that matter most. 5️⃣ The Right Way to Start the First Conversation Your opening determines whether you move forward or get brushed off. Use approaches that earn a real next step. If your deals keep stalling at “interested,” this episode gives you the buyer’s-eye view you need to close smarter and faster—straight from one of the most respected education leaders in the U.S. 📩 Want help structuring your pitch so education buyers say “yes”? DM me “Close” and I’ll walk you through it. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more founders can close bigger, better deals. #EdTech #FounderSales #MessagingStrategy #EdSales #ChannelSales #EducationInnovation #BreakingTheGrade #ClarityConverts #GrowthStrategy

    24 分钟
  5. (Re-Air) The Signature Solution: Your Proven Blueprint to a Clear Offer That Generates Leads and Wins the Education Market

    8月17日

    (Re-Air) The Signature Solution: Your Proven Blueprint to a Clear Offer That Generates Leads and Wins the Education Market

    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’t just still relevant in 2025—it’s required for founders who are booking calls but can’t consistently close. In this re-aired conversation, I go deep on the one tool that turned my “good pitch” into a clear, closeable, and irresistible offer to my perfect client — The Signature Solution. Before I had it? ❌ Closing deals felt like a coin toss. ❌ Prospects nodded… but didn’t buy. Now? 💥 Prospects instantly see the value, understand my model, and sign. 🎙️ This episode is your step-by-step reset to package your expertise, clarify your offer, and close more deals — without adding more calls, posts, or pitches. 🎯 3 Big Takeaways for Education Founders 1️⃣ The Confused Mind Doesn’t Buy Your buyers aren’t saying no—they’re saying “I don’t get it.” 👉 If your offer isn’t converting, it’s not what you’re selling — it’s how clearly you present it. 2️⃣ Framework > Features What sells isn’t your product’s capabilities—it’s your unique method. 👉 When you show your system, people lean in. Because clarity breeds confidence. 3️⃣ Your Offer Is Your Differentiator Most founders try to sound impressive. I chose to sound obvious—to the right audience. 👉 In crowded markets, the clearest offer wins. Not the loudest one. 🧠 This episode isn’t about cute frameworks. It’s a tactical reset for education founders ready to close smarter, faster, and more often—with a pitch that actually works. 📩 Want help building a Signature Solution that turns your expertise into a lead gen machine? DM me “Signature” and I’ll walk you through how we build one inside the EdSales Elevation Experience. 🚀 Or, grab my FREE Step-by-Step Lead Generation Blueprint and map out your own 90-day plan to consistently book 5–10 high-quality sales calls each week (without ads or content burnout). 👉 Download your FREE Lead Generation Blueprint here 📤 Know an education founder stuck in pitch mode? Send this episode before they burn another quarter on the wrong message. Because in EdTech, Clarity isn’t optional. It’s the close. #EdTech #LeadGen #FounderSales #MessagingStrategy #SignatureSolution #ClarityConverts #EdSales #SalesBlueprint #BreakingTheGrade

    17 分钟
  6. From $10M in Sales to Losing Her Company: What Education Founders Learn the Hard Way About Selling, Scaling, and Staying Aligned

    8月10日

    From $10M in Sales to Losing Her Company: What Education Founders Learn the Hard Way About Selling, Scaling, and Staying Aligned

    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 later? She was fired from the very company she built. 💥 Because when your backend can’t keep up with your bookings, you’re not scaling. You’re stalling at a higher speed. But here’s what makes this episode different: Jolene didn’t disappear. She didn’t burn out. She didn’t bow out. She doubled down on the mission—and came back sharper, stronger, and more strategic than ever. In this episode of Breaking the Grade, Josh sits down with Jolene Levin——to unpack what happens when you sell fast, scale hard, and survive the fallout. ✅If you're leading your own sales and chasing growth, this one shows you where most founders break—and how to rebuild smarter 🔑 5 Big Takeaways for EdTech Founders 1️⃣ Why Most Founder Pitches Fail Before They Start Jolene never “sold furniture”—she sold outcomes. And that mindset shift is the first step founders need to make to stop confusing buyers and start driving outcomes. 2️⃣ The Hidden Risk of Selling to the Wrong Buyer Not every school is your customer. Jolene explains how she identified who not to sell to—and why filtering for fit was key to her growth. 3️⃣ Why Understanding Buyer Motivation Beats Any Sales Script Jolene explains how she closed high-ticket deals by deeply understanding what school leaders cared about—and connecting her solution to those priorities, not her pitch. 4️⃣ Why Value > Volume in Sales Strategy Instead of chasing every contract, Jolene doubled down on districts who aligned with her mission. The result? Bigger deals with better outcomes. 5️⃣ The Real Cost of Frankensteined Funnels Disconnected CRMs, duct-taped follow-ups, and reactive workflows? Jolene’s story is a case study in what not to build—and how to reset. If your sales calls are stacking up—but your backend can’t keep up—this is your reset. 📩 DM me “Scale” and I’ll show you how to structure founder-led sales to grow without burning out. 📤 Know a founder chasing growth without a plan for scale? Send them this episode. It might save them from breaking what they’re building. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more founders can turn big sales into smart growth. #EdTechSales #FounderLedGrowth #SalesSystems #JoleneLevin#EducationInnovation #ScalingSales #GrowthStrategy #BreakingTheGrade #EdSales

    26 分钟
  7. (Best of) Your Demo Is the Problem: What Education Founders Must Do—and Stop Doing—to Close More Deals With Their Demos

    8月3日

    (Best of) Your Demo Is the Problem: What Education Founders Must Do—and Stop Doing—to Close More Deals With Their Demos

    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 go from pitch mode to purchase orders—without sounding like a salesperson. On October 11, 2024, I sat down with John live at the height of demo season—and what he shared still hits just as hard today. 💥 And here’s the controversial truth: Most demos aren’t just ineffective—they’re repelling your buyers. EdTech founders are over-investing in decks and under-investing in clarity. And that disconnect? It’s killing conversion. I’m re-airing this episode because too many EdTech founders are still demoing like it’s 2013. Polished decks. Zero traction. With back-to-school chaos heating up, your demo can’t just look good. It has to convert. If your demo is polished but not converting, this episode will help you course-correct fast. 🔑 3 Big Takeaways for EdTech Founders 1️⃣ Flip the Script with the ABC Demo John’s high-converting framework flips the usual “features-first” pitch on its head. 👉 Start with the buyer’s priorities, link to real funding buckets, and frame your product as a strategic solution—not a wishlist of features. 2️⃣ Start a Conversation—Not a Pitch Top founders don’t pitch. They guide trust-building conversations. 👉 Use soft openers like “I may have this wrong, but…” to lower resistance and invite collaboration. That small shift? It can change everything. 3️⃣ The Demo Isn’t a Meeting—It’s a System John maps the whole journey—from when to drop a Loom video, to how to follow up after ghosting. 👉 Demos that close aren’t flashy. They’re structured and strategic. If your sales calls fade fast—or your “great pitch” keeps getting ghosted—this is your reset. 📩 DM me “Demo” and I’ll show you how to restructure your pitch using John’s proven ABC framework. 📤 Know an EdTech founder demoing features like it’s 2013? Send them this episode. It could save them a pipeline full of wasted calls. Because in EdTech, The clearest, most contextual message wins. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education founders can turn clarity into traction. Thanks for tuning in to Breaking the Grade. #EdTechSales #FounderLedGrowth #SalesStrategy #JohnGamba #EducationInnovation #DemoStrategy #BuyerAlignment #ClarityConverts #BreakingTheGrade #EdSales #PennGSE

    35 分钟
  8. From Collapse to Credibility: Robert Martellacci’s Blueprint to Win Back Influence and Close Deals in the Education Space

    7月27日

    From Collapse to Credibility: Robert Martellacci’s Blueprint to Win Back Influence and Close Deals in the Education Space

    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 influential gatherings of education decision-makers in North America, to unpack how he went from collapse to becoming one of the most trusted connectors in the EdTech space. And here’s what makes his story even more powerful: ✅ He worked alongside Kevin O’Leary (aka “Mr. Wonderful”) while helping develop Mattel’s EdTech products. ✅ He helped build Mattel’s EdTech division—before it was acquired for $3.6B. ✅ And today? He runs an ecosystem that keeps him booked, trusted, and closing high-leverage education partnerships. So if you’re a founder navigating market shifts—or trying to reposition your message so decision-makers say “yes”—this is your reset. 🎯 3 Big Takeaways for Education Founders 1️⃣ Reframe Your Edge Before the Market Does Robert didn’t wait to get picked. He pivoted, rewired his message, and claimed a niche that made him indispensable. 👉 In EdTech, traction belongs to the clearest communicator—not the loudest one. 2️⃣ Design a Business That Buys Back Your Life Revenue matters. But Robert built a company that also delivers access, margin, and freedom. 👉 If your calendar’s full but your tank is empty, this is your model for long-term wins without burnout. 3️⃣ Reinvention is a Sales Strategy From faculty hockey to boardrooms, Robert built trust by evolving, not retreating. 👉 Credibility isn’t claimed. It’s earned—one connection, one message, one reinvention at a time. If you’re in the messy middle of a pivot or chasing leads that don’t convert, this is your blueprint to shift fast and close smarter. 📩 Want help repositioning your offer so decision-makers say “yes”? DM me “Reinvent” and I’ll hop on a strategy call with you. 📤 Know an education founder stuck in pitch mode? Send this episode before they burn another quarter on the wrong message. Because in EdTech, Your leads follow your clarity. ✍️ Love the show? Subscribe on Apple and Spotify to help more education founders grow with purpose and precision. #EdTech #FounderSales #MessagingStrategy #Reinvention #EdSales #ChannelSales #EducationInnovation #BreakingTheGrade #ClarityConverts #RobertMartellacci #GrowthStrategy

    34 分钟

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Breaking the Grade is a thought-provoking podcast that follows entrepreneurs in the education space as they make their way to the top. Tune in for stories about breaking norms, introducing new ideas, and shaping our future society through every lesson let out.