EdSales Edge Show
EdSales Edge is the strategy podcast for education founders, consultants, operators, and leaders selling into education.
For years, this show was known as Breaking the Grade, a space to challenge the status quo in education and think differently about how change actually happens. That mission hasn’t changed.
But the work has.
Over time, one thing became clear:
Education founders don’t just need inspiration.
They need clarity.
They need real strategies for selling into schools.
They need predictable ways to generate leads.
And they need to understand how trust is built in a system that doesn’t move fast, and doesn’t give many second chances.
EdSales Edge was rebuilt to match that reality.
Hosted by Josh Chernikoff, a two-time education founder who’s built and exited companies in this space, the show breaks down how selling into education actually works—across B2C, B2B, B2B2C, and B2E—always through the lens of how education institutions really make decisions.
This is not a show about hacks, shortcuts, or quick wins.
Education doesn’t work that way.
On EdSales Edge, you’ll hear:
- Real strategy for selling into education systems
- Conversations with education decision-makers who explain how buying actually happens from the inside
- Stories from founders, CEOs, and operators who’ve built real traction selling into schools—what worked, what didn’t, and what actually moved deals forward
- Teachings from the EdSales Elevation Experience, the system used to help education founders move from unclear and invisible to trusted and in demand
You’ll learn how to:
- Define your Perfect Client
- Pull the right credibility lever
- Move from being hidden… to trusted… to building a real lead engine
Josh is joined by his good friend and mentor, John Gamba—Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, and a former education founder who’s led companies through real growth and successful exits. John brings the institutional lens, shaped by years inside districts, universities, and education systems, seeing how decisions get made when the doors are closed and what earns trust over time.
Together, they sit on both sides of the table, the builder side and the system side, so the show stays grounded in reality, not sales theory.
If you sell into education and you’re tired of guessing,
guessing who to talk to,
guessing how decisions get made,
guessing why interest doesn’t convert—
this show is built for you.
EdSales Edge
Clarity. Credibility. Real traction.
If you sell into education, this is where you earn your edge.
EdSales Edge Show
The most powerful tool to connect with your ideal clients
Summary
In this episode, Josh Chernikoff discusses how to confidently start conversations with potential clients that lead to booking more calls. He addresses the challenge of initiating conversations and offers strategies for building rapport and making connections. Josh emphasizes the importance of offering value and following up with potential clients. He provides tips for opening conversations, such as starting with a warm personalized greeting and getting people talking about themselves. Josh also highlights the value of creating a supportive community and helping clients get comfortable with initial conversations. He invites listeners to join the Ed Sales Elevation Experience and emphasizes the transformative impact of starting conversations.
Takeaways
- Discover your most powerful tool to connect with your ideal clients in a natural and comfortable way.
- My #1 tip for initiating conversations that flow naturally and lead to results: like booking more sales calls and wanting to know how to work with you!
- Find out 5 things I do when reaching out to cold leads… that gets results.
- One tool you MUST have if you want to stay on top of your leads, build strong relationships and convert them into happy clients…
- PLUS hear real-life examples, like Katherine's story about how she finally felt confident to reach out and connect with an ideal client… that booked a sales call effortlessly.
Chapters
00:00 Introduction and the Challenge of Starting Conversations
02:21 Building Rapport and Making Connections
03:19 Offering Value and Follow-up
05:15 Tips for Opening Conversations
07:30 Creating a Supportive Community
08:28 Helping Clients Get Comfortable with Initial Conversations
09:28 Joining the Ed Sales Elevation Experience
10:07 The Impact of Starting Conversations
11:22 Conclusion and Call to Action
