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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
Why the Fastest “Yes” Beats the Biggest Budget — with Dr. Brooke Olsen-Farrell
Selling into education rewards clarity, not size. Long cycles, layered decisions, and committee-based buying can quietly drain a founder’s runway, especially when growth is tied to landing “big name” districts.
In this episode of EdSales Edge, Josh sits down with Dr. Brooke Olsen-Farrell, a nine-year Superintendent at Slate Valley Unified School District and a national policy leader. Together, they unpack why traction in education doesn’t start with the biggest budgets, it starts with the Perfect Client.
If you’re stuck chasing prestige logos while momentum stalls, this conversation will help you rethink where real growth actually comes from.
WHY THIS MATTERS
Most education founders don’t struggle because their solution isn’t strong.
They struggle because they’re selling into systems that move slowly — while their business can’t afford to wait.
Chasing large districts often feels strategic, but in reality it introduces long procurement cycles, diluted ownership, and endless “almosts.” This episode reframes growth around speed, belief, and influence, not size.
KEY TAKEAWAYS FROM THIS EPISODE
1. Perfect Client isn’t the biggest district, it’s the fastest mover
Traction comes from leaders who can decide, test, and implement quickly. Smaller or mid-sized districts often provide the proof points and revenue founders need to survive and scale.
2. Research beats relevance every time
Dr. Brooke shares the simple filter she uses when evaluating outreach: did the founder take time to understand her district’s goals? Generic pitches get deleted. Contextual ones get opened.
3. Stop selling finished products, start co-creating
Superintendents don’t want to be sold to. They want to partner. Positioning your offer as something they can help shape lowers resistance and builds trust faster than polished decks ever will.
4. One right pilot can unlock an entire state
A successful implementation with the right leader doesn’t stop at one district. Brooke explains how she shares trusted partners across networks like AASA, turning one “yes” into many.
5. Early-stage resilience is an asset, not a liability
Being transparent about where you are, and showing responsiveness, can outperform large publishers. Leaders value partners who listen and adapt, not vendors who lecture.
A MOMENT THAT STOOD OUT
One of the most telling moments in this conversation is when Brooke explains why she deletes dozens of cold emails a day, not because the ideas are bad, but because they ignore her reality. The founders who stand out aren’t louder or flashier; they’re prepared, curious, and aligned.
WHO THIS EPISODE IS FOR
This episode is for:
- Education founders and CEOs
- Consultants and operators selling into districts or education institutions
- Leaders navigating long cycles and high-trust buying environments
If you want traction without burning the runway, this conversation will resonate.
NEXT STEP
If this episode helped you rethink who you’re actually selling to, you don’t have to sort that out alone.
You can DM TRACTION to learn how founders inside the EdSales Elevation Experience identify, co-create with, and close their Perfect Clients, without chasing prestige or waiting on the “big yes.”
Details are in the show notes.
SUBSCRIBE & SHARE
If you found this episode valuable:
- Follow or subscribe to EdSales Edge
- Share it with another education founder who’s stuck chasing big districts and getting nowhere
Clarity compounds when it’s shared.
