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

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

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

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

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!

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!

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

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.