Breaking the Grade
Breaking the Grade is a thought-provoking podcast that follows entrepreneurs in the education space as they make their way to the top. Tune in for stories about breaking norms, introducing new ideas, and shaping our future society through every lesson let out.
Breaking the Grade
Best of 2025: Karim Kuperhause & Rose Hastreiter on Why Education Founders Must Sell First, Master Objections, and Build a Repeatable Process Before Delegating or Scaling
Some episodes can't just be missed… this one is one of them.
Why? Because it shifts how education founders think about sales, delegation, and building predictable pipelines.
Originally streamed as a LinkedIn Live in October 2025, this replay brings back one of the most tactical, mindset-shifting conversations of the year.
When Karim Kuperhause, CEO and Founder of HierSales, joined Josh for a candid LinkedIn Live conversation, later joined by Rose Hastreiter, founder and CEO of Leonty3C, the discussion went deeper than closing deals.
They explored the education founder’s role in early sales, how to uncover the real objections hiding behind “surface complaints,” and the steps to systematize sales so that growth isn’t reliant on the founder alone.
Karim, an experienced entrepreneur and education sales strategist, explained why it’s crucial for education founders to lead initial sales conversations, not just to close the deal, but to truly understand what prospects care about, what frustrates them, and why objections often mask the real barrier to saying yes.
Rose added critical insight on testing messaging, iterating offers, and embedding empathy into every sales touchpoint, showing how thoughtful sales processes build trust and open doors for scalable growth.
From learning how to read beyond objections to creating repeatable sales systems, this episode offers a masterclass in the mindset education founders need to confidently delegate, but only after the process is proven and repeatable.
🚨 Your sales team can’t close what you haven’t first validated yourself, and your next rep won’t succeed without a repeatable process.
What You’ll Learn in This Episode
1️⃣ Uncover the Real Objection
How to ask questions that reveal the underlying problem, not just the surface complaint. Objections are often emotional, not logical.
2️⃣ Selling Before Delegating
Why founders must lead the first sales conversations to validate offers, messaging, and target audiences before hiring a sales rep.
3️⃣ Build a Repeatable Process
The key to scalable sales is repeatability. You can train a team effectively, only after you’ve systematized success.
4️⃣ Test, Iterate, Refine
How to use campaigns, cold calling, and feedback loops to continuously refine your offer and messaging.
5️⃣ Empathy as a Competitive Advantage
How addressing objections thoughtfully and demonstrating understanding builds trust and positions your solution as aligned with client priorities.
If you’ve ever struggled to delegate sales, felt objections stopping deals, or wanted a process that actually scales, this episode will give you both mindset and tactical clarity.
📩 DM me “DELEGATE” and I’ll show you how education founders inside the EdSales Elevation Experience validate offers, systematize sales, and build pipelines that scale.
📤 Know a founder who’s stuck doing all the selling themselves? Share this episode, it’s the clarity they’ve been missing.
✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education founders can sell smarter, scale faster, and delegate confidently.
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