Breaking the Grade

$9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore

Josh Chernikoff

Most education founders don’t fail because of bad ideas.

They fail because they lean too hard on “AI-powered” buzzwords, skip the research-to-practice proof buyers demand, and don’t form the partnerships that give them credibility and attract the right leads.

That’s the cycle YourWay Learning set out to break.

Back in January, at the IFE Conference in Monterrey, Mexico, I sat down with Jaime Palés, co-founder and president of Yourway Learning, with 20+ years of global experience scaling educator training and AI-driven learning models— and Michael Golden, Vice Dean of Innovative Programs and Partnerships and Executive Director of Catalyst at Penn GSE and ex-Microsoft exec

At the time, YourWay was still early—focused on building with intention, grounding in research, and designing tools teachers would actually use.

Fast forward: they’ve raised $9 million and launched a partnership with Penn GSE turning credibility and strategic alignment into a pipeline of opportunities.

This episode takes you back to that conversation—before the headlines—showing how YourWay built the foundation that turned momentum into investments and qualified leads.


5 Big Takeaways for Education Founders

1️⃣ AI Isn’t the Differentiator—Your Approach Is
Buzzwords don’t close deals. Clear, outcome-driven solutions do and they attract schools, districts, and buyers actively looking to invest.

2️⃣ Research to Practice = Credibility
Buyers don’t want “feel good” workshops. They want evidence your AI or EdTech solution drives measurable classroom impact—your strongest lead-generation tool.

3️⃣ Your DNA as a Founder Matters
Persistence, humility, and community separate ventures that scale from those that fade—especially in the long sales cycles of education.

4️⃣ Partnerships Trump Solo Play
The fastest path to traction is aligning with research institutions, accelerators, and trusted partners who validate your model—and bring you in front of qualified buyers.

5️⃣ Mission + AI + Partnerships = Long-Term Wins
Quick cash grabs don’t last. Buyers back founders who balance innovation with credibility and sustainability. 

YourWay’s story proves that when vision, credibility, and timing align, momentum turns into millions. The lesson is clear: lead with outcomes, use AI with intention, and anchor growth in partnerships that last.


📩 DM me “Momentum” and I’ll show you how to structure your growth story so buyers and investors notice—and respond.

📤 Know a founder chasing buyers with AI hype but no real partnerships?
Send them this episode. It might save them from losing deals before they scale.

✍️ Love the show?
Subscribe on Apple Podcasts and Spotify so more education founders can turn AI innovation + strong partnerships into consistent sales growth.

#EdTechSales #FounderLedGrowth #AIinEducation #PartnershipsThatScale #ResearchToPractice #SalesStrategy #GrowthStrategy #BreakingTheGrade #EdSales



People on this episode