Breaking The Grade podcast

26:18

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 & Partnerships at Penn GSE . These two educational innovators share their insights from the frontlines of EdTech and higher education. They reveal the critical mistakes businesses make when implementing AI without a solid partnership strategy, and what it actually takes to build impactful collaborations. We also dive into how AI and partnerships can solve real problems for education businesses, from attracting students to scaling operations. This episode is for you if you're wondering how to navigate the AI landscape and forge partnerships that deliver results. Tune In to Hear: The common pitfalls of AI adoption: Why simply implementing AI won't guarantee growth, and what crucial steps businesses often overlook. How strategic partnerships amplify AI's impact: The specific ways collaboration can solve challenges that AI alone can't address. The key elements of successful EdTech partnerships: What education leaders and founders must focus on to build collaborations that drive sustainable growth. Why a clear understanding of your business needs is crucial before investing in AI: How to avoid the trap of chasing trends without a solid strategy. The practical steps to attract more students and scale impact using AI and partnerships: Real-world examples and actionable advice for education businesses. What decision makers need to know to make AI adoption a success. If you run an education business, this episode is a must-listen. #EdTech #AIinEducation #StrategicPartnerships #BreakingTheGrade #LeadGeneration ------ Josh Chernikoff LinkedIn EdSales Elevation Experience…

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Why Most Startups Get Investment Wrong—and How to Fix It 21:07

17 days ago21:07

21:07

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 you’re actually ready for investment, and why a strong lead generation system is a must before you even think about bringing on investors. If you're debating whether to seek investment or go it alone, this episode will help you figure out the right next step. Tune In to Hear: The warning signs that you’re pitching too early — and what investors really want to see. How to tell if your business needs more capital — or just a better sales strategy. Why funding isn’t always the answer — and what might be holding you back instead. The hidden costs of taking investment: What no one tells you about giving up equity and control — and how to make the right call. Why so many education entrepreneurs chase investment too soon — and what to focus on instead to grow sustainably. Why more money won’t fix a broken sales pipeline: The crucial step education founders must take before seeking investors. Chapters 00:00 - Introduction to Funding vs. Bootstrapping 02:59 - Understanding the Pros and Cons of Investment 10:00 - Identifying the Right Time for Investment 15:09 - Bootstrapping Strategies for Growth 21:59 - Preparing for Investment: Key Benchmarks 26:47 - Final Thoughts and Call to Action Links Josh Chernikoff Josh Chernikoff LinkedIn…

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Before You Hire a Sales Team...The Steps Founders Can’t Skip 18:33

6 weeks ago18:33

18:33

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 without the growing pains, this episode has the answers you need. Tune in to hear: The hidden risks of scaling your sales team too quickly — and the strategy to scale with purpose and precision. How to ensure your first sales hire is the right one for your business — without wasting time and money. Why premature hires can slow down your sales cycle — and how to know when you're truly ready to scale. How understanding the difference between a founder’s sales role and a sales team’s role can transform your revenue potential. Chapters 00:00 When to Hire a Sales Team 07:59 The Importance of Founder-Led Sales 13:48 Leveraging LinkedIn for Founders and Sales Teams 21:23 Key Takeaways and Final Thoughts Links Josh Chernikoff LinkedIn Edsales Elevation Experience Masterclass The 2025 Annual Sales Planner…

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Secrets behind unlocking 7-figures in sales...How this seasoned entrepreneur transformed his sales process. 26:23

8 weeks ago26:23

26:23

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 networking can shift your business, and the role LinkedIn plays in connecting with decision-makers. If you're looking to grow your business in a competitive market, this conversation is full of strategies you won’t want to miss. Tune in to hear: The one tool that transformed Ernie’s business and unlocked 7 figures in proposals setting him up for a successful 2025 - and how you can too! The power in re-evaluating your business model and setting yourself up to thrive. Why rejection can be the key to uncovering your biggest business breakthroughs. The game-changing power of selling year-round—and how to make it happen. Why being able to start delivery of your program at any time of the year (instead of just the start of the school year) can open you up to big sales opportunities. The power of a strong LinkedIn presence—and why it’s essential for building meaningful connections. Chapters 00:00 - Introduction to Beyond Technology Education 05:56 - Navigating Marketing Challenges in Education 11:55 - Understanding the Education Sales Cycle 18:14 - Future Aspirations for Ernie and Beyond Technology Education Links Ernie Delgado Beyond Technology Education Edsales Elevation Experience Masterclass…

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From One-Off Sales to Repeatable Revenue...How Future Makers Transformed Their Business 34:49

10 weeks ago34:49

34:49

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, your strategy just stops working. So how do you navigate these challenges and come out stronger? In this week’s episode, Matt shares exactly how he transformed Future Makers and set it up for success. Whether you’re building from scratch or looking to scale, Matt’s story is packed with actionable insights to thrive no matter what’s thrown your way. Tune in to Hear: ✅ How to navigate big challenges in your business (like pivoting!). ✅ The biggest challenge Matt faced in pivoting his business —and how he overcame it. ✅ Why Matt’s messaging shifts made it easier than ever to spot—and attract—the perfect fit clients (and how you can too!) ✅ The surprising truth about building relationships at scale (it’s not what you think!) ✅ The exact steps Matt took to build a powerful lead generation system so that he could scale —and how you can do it too! And if you’re ready to build your lead generation system then join my FREE Masterclass: How to get more leads and sales on repeat (without paid ads or creating endless content that no one sees!) Chapters: 00:00 - Introduction: Setting the Stage 03:01 - The Importance of Having a System 05:54 - Building Relationships for Success 08:20 - Challenges in Creating a Signature Solution 12:09 - The Role of Listening in the Sales Process 14:01 - The Implementation Process: Highs and Lows 17:54 - Measuring Impact and Growth 22:40 - Evolving the Signature Solution 28:12 - Communicating Value and Building Credibility 30:44 - Trusting the Process and Embracing Iteration 34:06 - Closing Thoughts on Growth and Business Evolution Links Matt Barinholtz Future Makers Edsales Elevation Experience Masterclass…

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Mastering Sales Planning in the Education Space 31:29

13 weeks ago31:29

31:29

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 momentum now for the year ahead. Tune in to hear: ✅ How to set yourself up for success and hit the ground running in Q1, so you can crush your sales goals! ✅ What you must do during the low seasons, to make sure you're selling during the high seasons... ✅ How to maximize your time in December to set yourself up for success and why waiting until January puts you at a disadvantage ✅ Why waiting until January puts you at a disadvantage ✅ Strategies to stay ahead in a competitive, seasonal sales cycle ✅ And what you need to be focusing on each month with specific actionable steps - to crush your sales goals in 2025! Timestamps: Introduction to the Episode (00:00:00) Importance of Pre-Planning (00:01:35) Sales Cycle Breakdown (00:03:19) Maximizing the Sales Window (00:05:04) Budgeting Conversations (00:06:47) Active Outreach Strategies (00:07:43) Creating Awareness (00:08:49) Generating Leads (00:10:29) Overcoming Fear in Sales (00:11:05) Setting Actionable Goals (00:12:45) Benefits-Driven Messaging (00:14:13) Goal Setting for Sales (00:15:30) Nurturing Leads in Summer (00:17:55) Sales Cycle Dynamics (00:19:56) Rejection and Resilience (00:21:05) Building Relationships in Sales (00:22:54) Understanding Market Readiness (00:23:39) Nurturing Leads (00:24:33) Effective Follow-Up Strategies (00:25:07) Tracking Outreach Efforts (00:25:25) Taking Action on Lead Generation (00:29:00) Closing Thoughts for 2025 (00:30:14) Links Planning Document Edsales Elevation Experience…

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Mastering the Education Sales Cycle & Secrets to Staying Top of Mind and Closing Deals 18:07

15 weeks ago18:07

18:07

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 and tough competition, this episode reveals why patience and strategy are your best tools. But be warned—it's not all about playing it safe. Discover what it really takes to thrive as an entrepreneur in education. The answers might not be what you expect. Tune in to hear: Why focusing only on selling is losing you sales and what you need to do instead... if you want to have sales coming in all year round. The one tool you’re probably not using that will boost your outreach and keep prospects engaged. My best tip to handle objections and turn them into your biggest opportunities . The secret to staying top of mind so schools reach out to you! Chapters 00:03-01:36 Introduction: The Warrior's Mentality 01:36-02:51 The Complex Sales Cycle in Education 02:51-04:52 Multiple Stakeholders and How to Navigate Them 04:52-07:07 The Story of Overcoming Data Privacy Obstacles 07:07-09:25 Managing the Long Sales Cycle 09:25-11:32 Identifying and Engaging Your Ideal Client 11:32-13:31 Building Momentum with Strategic Follow-Up 13:31-15:46 Personalized Outreach and Staying Engaged 15:46-17:27 Overcoming Resistance to Change 17:27-19:11 Patience and Persistence in the Long Sales Cycle 19:11-20:33 Success Story: Lafayette Elementary 20:33-22:59 Managing Multiple Leads and Opportunities 22:59-End Conclusion: Patience, Persistence, and Pleasantness Want more help getting leads and sales? 👉 ✨ Book a FREE strategy call with me. Together we'll look at your entire lead gen system and see where you need to focus to start bringing in high-quality, high-converting leads!…

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Why Waiting to Sell in the Education Sector Can Cost You...& when’s the right time to start selling 17:30

17 weeks ago17:30

17:30

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 relationships that will pay off later. He shares actionable insights on how to engage with your ideal clients even before they’re ready to buy, building trust and awareness that makes your product or service their obvious choice when the time comes. If you’re ready to crack the timing code for education sales, this episode is for you. Takeaways: Why waiting for perfection is the fastest way to miss opportunities … and what you need to do instead to start generating leads now! What does a centuries-old shipwreck have to do with your business? How to handle seasonality in education sales and why it’s not as tricky as you may believe What lessons you can learn from 10-year-olds that will completely transform your sales approach Discover why getting in front of your audience sooner than later can actually speed up your sales cycle. Chapters: 00:00 - Introduction: The Challenge of Timing in Education Sales 03:05 - Why Waiting Until the Last Minute Can Cost You 06:47 - Building Relationships Before They’re Ready to Buy 10:21 - Aligning with the School Year and Budget Cycles 14:36 - Trust-Building Strategies that Pay Off Later 17:54 - Key Takeaways and Next Steps Want more help getting leads and sales? 👉 ✨ Book a FREE strategy call with me . Together we'll look at your entire lead gen system and see where you need to focus to start bringing in high-quality, high-converting leads!…

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A Better Approach to Sales Calls for Education Companies… How to sell without being salesy. 19:31

19 weeks ago19:31

19:31

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 sounding like just another salesperson. And here’s the kicker: he shares why the best salespeople aren’t just listening—they’re also storytelling in a way that hooks prospects and keeps them engaged. Want to know exactly how he does it? There’s only one way to find out. Listen now and see why this small tweak could completely change your results. Takeaways: Find out why focusing on features is costing you sales—and what to shift your attention to instead. The one move that's damaging your sales relationships—fix it, and watch sales flow effortlessly. Why most people struggle to sell on virtual meetings and how to instantly build trust and form strong connections… Discover the quick way to build instant trust and bust through objections without being salesy. Chapters: 00:00 - Introduction to Effective Sales Calls 02:48 - The Shift from Talking to Listening 05:52 - The Power of Active Listening 09:12 - Building Connection and Trust 12:03 - The Self-Identification Call 15:01 - The Importance of Storytelling 19:54 - Conclusion and Key Takeaways Want more help getting leads and sales? 👉 ✨ Book a FREE strategy call with me. Together we'll look at your entire lead gen system and see where you need to focus to start bringing in high-quality, high-converting leads! 🔗 www.joshchernikoff.com/call…

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The Better Demo Method To Sell More Education Services & Products 31:45

21 weeks ago31:45

31:45

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 between meetings to handling tough questions from tech experts, we’ll show you how to turn a demo that’s going off track into a win. If you’ve ever struggled with technical problems or pushback during a demo, this episode will give you practical tips to recover and close the deal with confidence. Key Takeaways: The surprising reason why your demos may fall flat—and how a strategic video sent at the right time could change everything. A simple technique to handle tough technical questions without derailing your sales momentum. Why demos go wrong more often than you think, and the key shifts that can turn a bad pitch into a win. The art of sending personalized demo follow-ups that show prospects you're truly listening—learn how to nail this crucial step. How to manage those "bad apples" in the room who seem determined to poke holes in your pitch—and flip the situation in your favor. This episode is a must-listen for any entrepreneur in the EdTech space looking to sharpen their sales approach and turn potential pitfalls into powerful selling points! Chapters: Introduction to the Episode (00:00:00) Guest Introduction (00:01:00) The Importance of Demos (00:01:17) Guided Conversations in Demos (00:03:29) Consultative Selling Approach (00:04:41) Benefits Over Features (00:06:01) Contextual Selling (00:07:01) Using Strategic Plans Effectively (00:07:56) Engaging with Prospects (00:10:08) Learning from Successful Demos (00:12:29) Demo Timing Considerations (00:16:39) Using Video for Demos (00:18:56) Listening to Client Needs (00:20:08) Personal Experiences with Demos (00:22:25) Lessons from Demo Failures (00:23:16) Understanding Security Concerns (00:24:19) Technical Preparedness in Demos (00:25:34) Utilizing Feedback Effectively (00:26:44) Handling Technical Questions (00:27:42) Staying Calm During Challenges (00:28:34) Post-Demo Follow-Up (00:29:36) Learning from Challenges (00:30:27) Importance of Practice (00:31:01) Closing Remarks and Community Engagement (00:31:26) Resources or Links: Connect with John Gamba: LinkedIn Interested in Growing Your Education Business? Book your FREE Strategy Call with Josh .…

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How This EdTech Company Transformed Their Sales Process And Went From Stagnation to Leads In Just 8 Weeks 31:07

23 weeks ago31:07

31:07

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 you've ever thought sales has to be pushy and you want a way to sell that feels good to you, then you're going to love this episode! Tune in to hear: My #1 tool for getting potential clients to open up and start talking to you ... How to build relationships that make selling easy and natural... Why most founders make a crucial mistake that can cost them months of wasted effort -- and what to do to avoid that. Why EdTech sales is different to other selling and how they overcame some big challenges in generating leads. PLUS, learn how to embrace objections, failures, and challenges as vital opportunities for growth in your business! Chapters 00:00 Introduction and Background 04:05 Challenges Faced by Rocket PD 09:42 The Coaching Process and Milestone Coaching 15:19 The Impact of the Signature Solution 22:32 Results and Successes 30:56 The Enjoyment of the Coaching Experience Here's how you can connect with RocketPD: Chris Dekmar LinkedIn Corey Murray LinkedIn RocketPD LinkedIn RocketPD Interested in Growing Your Education Business? Want my eyes on your business? Book your FREE Strategy Call here. JoshChernikoff.com EdSalesElevationExperience.com…

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How this EdTech Startup sharpened their message & went from struggling to selling! 23:33

27 weeks ago23:33

23:33

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 MyOwl off the ground. MyOwl is an app that brings student's homework assignments into one centralized dashboard. The average student today has to use more than 143 apps to get their homework done. Talk about a logistical nightmare! So, when Brent and his daughter told other parents about their idea, the parents couldn't wait to get their hands on it. But when he tried to get the app partners on board and schools on board, it felt like he was banging his head against the wall... Key Takeaways: Tune in to hear… Why having a great product wasn’t enough—and the game-changing move Brent made to get schools on board . The crucial shift in his messaging that turned MyOWL from a “ maybe ” to a “ must-have. ” The surprising power of community —how being part of a group of other education founders gave him the breakthrough he needed. AND… hear all about his experience inside the 3E EdSales Elevation Experience. Chapters 00:00 MyOWL: Revolutionizing Homework Management 05:30 The Impact of the Ed Sales Elevation Experience 10:55 The Power of the Mastermind Group 13:46 Networking and Support for Education Entrepreneurs 21:09 Join the Homework Revolution with MyOWL Resources/ Links: Connect With Brent Newton: Brent Newton | LinkedIn Go to MyOwl Website: myOwl | Homework Managed Interested in Growing Your Education Business? Book your FREE Strategy Call. Learn More about the 3E Edsales Elevation Experience: Join the waitlist for the next cohort here.…

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How this EdTech founder got clarity on his ideal client & product... making selling easier! 26:29

29 weeks ago26:29

26:29

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, focusing your message, and attracting the right clients. Sam’s story is a must-listen for anyone looking to transform their approach to business and achieve long-term success. Key Takeaways: The game-changing realization Sam had about why his first product wasn’t selling —and how you can apply the same insight to your business . How Sam’s pivot to a new market led to a dramatic increase in quality leads and sales —find out the strategy behind it. The exact steps Sam took to simplify his product and make it irresistible to his ideal clients—learn how to do the same. How joining a cohort-based program transformed Sam’s sales strategy and what you can gain from similar opportunities. Why having a long-term vision is crucial for entrepreneurial success and how Sam’s perspective shift helped him thrive. Don’t miss this episode packed with actionable advice and real-world insights that can transform your approach to entrepreneurship! Chapters: 00:00 Introduction and Background 03:08 Aligning Sales Approach with Values 06:26 The Power of Focusing on One Product 14:36 The Value of Feedback and Cohort-Based Programs 19:24 Pivoting to a New Product 21:16 Building a Roadmap and Confidence Resources or Links: Connect with Sam Saarinen: LinkedIn, Quizius Learn More about the 3E Edsales Elevation Experience : Join the waitlist for the next cohort here. Interested in Growing Your Education Business? Book your FREE Strategy Call with Josh . Tune in to discover how focusing on the right strategies can lead to extraordinary results!…

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3 Powerful Systems To Grow Your Education Business With More Ease 26:57

31 weeks ago26:57

26:57

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 important to embrace imperfection and learn from them. Takeaways Implementing systems is crucial for scaling and growing an education business. A repeatable and scalable offer is essential to attract and retain clients. Having a lead generation system helps automate the process of attracting and nurturing ideal clients. A delivery system ensures client success and automates tedious tasks. Embrace imperfection and learn from mistakes along the way. Chapters 00:00 Introduction and Importance of Systems 08:18 The Offer System 12:40 Lead Generation and Sales System 20:20 Delivery System and Client Success 23:25 Embracing Imperfection and Learning from Mistakes…

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3 Essentials To Grow Your Business: Lessons I Learned From Starting, Scaling, and Selling Flex Academies 21:29

33 weeks ago21:29