EdSales Edge Show

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:

• Why so many education companies fail when selling into schools and universities.
• How to align your messaging with how institutional buyers think.
• Why confidence and clarity matter more than features and flash.
• The power of understanding governance, policy, and internal processes before you pitch.
• Global and local opportunities in education—whether you're working in underserved markets like Latin America or navigating school districts in the U.S., speaking the language of decision-makers is key.

Michael’s experience in education policy, innovation, and navigating complex institutions is a masterclass in how to sell smarter, not harder.

🎯 Even if you typically sell only to universities or only to K–12 schools, the strategies we explore in this episode apply across the board. Institutions may vary, but the approach to building trust and gaining traction is universal.

🎯 If you’ve ever walked into a district meeting or university pitch and felt like you weren’t speaking their language—this episode is for you.

Want traction? Stop selling. Start positioning yourself and listening.

#EdSales #EducationBusiness #LeadGeneration #InstitutionalSales #MessagingStrategy #BreakingTheGrade

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

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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.

Here’s the truth: Business cards aren’t contracts.

Education companies do this unsuccessfully for a long time. They go to education conferences expecting immediate ROI, but conferences don’t work that way. They’re a slow burn strategy.

💡 Slow burn strategies are the things businesses know they need to do, but don’t execute well. Like LinkedIn engagement, email outreach, or running a sales pipeline—conferences fall into the same category. They don’t deliver overnight wins, but they are the foundation for building long-term credibility, trust, and business relationships that actually close later.

The companies that win at conferences don’t just show up hoping to make deals. They go in knowing that this is the start of a conversation, not the end of a sale.

That’s exactly what we’re breaking down in this special Coach’s Corner episode, recorded after my time at IFE in Monterrey and ERDI in Palm Springs.

🎙️ Tune in to Hear:

🔥 How education businesses can strategically choose the right conferences.
🔥 Why networking at conferences is about listening, not selling.
🔥 How follow-up and engagement after the event determine ROI.
🔥 Why smaller, targeted conferences are often better than big, crowded ones.
🔥 How clarity in your messaging and ideal client makes conferences more valuable.

💡 If you just listen, people will open up to you. The companies that win at conferences aren’t the ones pushing their product the hardest. They’re the ones who go in with a plan, focus on real conversations, and build relationships that turn into future deals.

#EdSales #LeadGeneration #EducationBusiness #ConferenceStrategy #BreakingTheGrade

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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

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Josh Chernikoff LinkedIn

EdSales Elevation Experience

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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.

• 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.

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

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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.

✅  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!)

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

Matt Barinholtz

Future Makers

Edsales Elevation Experience

Masterclass

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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!

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage

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!

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
Host, Edsales Edge Show

🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/

📩 Email: [email protected]

Join the Edsales Entourage

Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage