The Brutal Math of Product-Market Fit with Gil Quadros Flores

On the Predictable Revenue Podcast, host Collin Stewart sat down with Gil Quadros Flores, founder and CEO of CoGrader, to unpack the messy realities of building an EdTech startup. From identifying teachers’ deepest pain points to navigating long sales cycles, Gil’s story is a case study in how founder-led sales and an experimental mindset drive real traction.

For early-stage founders, especially in education, the key takeaways are clear: prove the concept before chasing profit, build trust before scaling, and continue iterating as the market shifts.

The Founder’s Leap

Every founder faces the moment when stability must give way to conviction. In EdTech, that leap can feel even riskier. Long sales cycles, slow adoption, and entrenched habits make progress hard to measure. 

However, this is precisely why early discovery and founder-led sales are crucial.

Take CoGrader as an example. Its founder didn’t start in education. He came from a background in consulting and corporate work. What mattered wasn’t his résumé, but that he immersed himself in the teachers’ world, listened to their biggest frustrations, and built directly for them. The lesson: you don’t need to be the customer, but you do need to live close enough to feel their pain.

And in those early days, no one else could sell the product on your behalf. 

Founders are uniquely positioned to handle the first sales conversations, not because they’re trained sellers, but because they understand the problem more deeply than anyone else. If you skip that step, you risk outsourcing the very insight that shapes product-market fit.

The founder’s leap isn’t just leaving a job. It’s committing to owning the problem, living in your customer’s world, and proving, with your own voice, that the solution matters.

Identifying Real Pain Points

Startups don’t fail because they lack ideas. They fail because they solve the wrong problems. The quickest path to traction is finding a pain point so sharp your customer can’t ignore it.

For CoGrader, that wedge was clear: grading. Teachers were spending nights and weekends buried in stacks of papers. It wasn’t just inefficient; it was draining their energy for the very work they loved. That kind of pain doesn’t need a 20-question survey to validate it. You can see it in the frustration on a teacher’s face when they describe their workload.

And that’s the key for founders: 

Emotional validation often tells you more than data points. If your customer lights up when they hear your solution, or breathes a sigh of relief when you describe the problem, you’re closer to product-market fit than any spreadsheet will show.

Think of product-market fit not as a box to check, but a spectrum. At the weak end, customers say, “Interesting.” At the strong end, they say, “Where have you been all my life?” Teachers’ reactions to CoGrader landed firmly on that strong end, confirming that the company wasn’t just building software, it was relieving real pain.

Early Sales and Market Validation

In the earliest stage, sales isn’t about profit, it’s about proof. Your goal isn’t to maximize revenue; it’s to optimize learning.

CoGrader approached early adopters with flexible pricing. The point wasn’t squeezing budgets. It was designed to remove friction, allowing teachers to try the product. For founders, this is a reminder: pricing is a tool, not a law. In the beginning, you’re trading margin for insight.

What mattered more than the dollars was the signal. 

Were teachers relieved enough by the product to keep using it? Did they tell colleagues? Those are the leading indicators of market validation. Profit can come later, conviction comes first.

And it’s the founder’s job to run these early pre-sales conversations. Delegating too soon risks losing the raw feedback that shapes your product. As the Predictable Revenue Manifesto notes, you can’t outsource your way to the first million. Founders must hear objections, feel hesitation, and adapt on the fly.

Early sales aren’t about closing deals. They’re about opening doors to customer truth.

Navigating Sales Cycles in Education

If you’re selling into education, be ready for a marathon, not a sprint. Sales cycles in this sector are famously unpredictable. Sometimes a teacher can adapt quickly, other times a district decision drags on for months. Budgets, approvals, and academic calendars all slow the pace.

That’s why patience isn’t optional. It’s a strategy. The founders who survive long cycles aren’t the ones pushing harder on deals. They’re the ones building trust while they wait.

For the CoGrader, this meant building a community of teachers who could share experiences and support one another. When sales stalled, relationships carried momentum. Teachers trusted the product because they trusted the people behind it.

The takeaway for founders: 

In education, the sales process is less about closing and more about compounding. Each conversation adds credibility. Each early adopter strengthens the case for the next. Play the long game, and you’ll find that trust, not pressure, is the real accelerant.

AI’s Growing Acceptance in Classrooms

A year ago, bringing AI into classrooms was a risky pitch. Many educators worried it would replace teachers or undermine learning. But attitudes are shifting fast. Today, the conversation is less “Should AI belong in schools?” and more “How do we use it responsibly?”

For founders, this shift matters. 

Timing can make or break adoption. The CoGrader benefited from launching at the moment when teachers transitioned from skepticism to curiosity. By framing AI as a tool that gave teachers time back rather than taking control away, they positioned themselves on the right side of the narrative.

The lesson: when markets evolve, you don’t have to reinvent your product, you have to reframe it. Listen closely to how customers are discussing technology now compared to a year ago. If you can align your story with their new mindset, adoption accelerates.

In education, AI stopped being the disruptor teachers feared and became the assistant they wanted. Founders who recognize and ride those shifts early build momentum that latecomers can’t catch.

Lessons for Founders

CoGrader’s journey leaves founders with three clear lessons:

1. Product-market fit is felt, not just measured. Metrics matter, but emotions reveal the truth more quickly. When customers light up, sigh in relief, or say “I need this now,” you’re closer to a real fit than any spreadsheet can prove.
2. Early community is as valuable as early revenue. Revenue validates demand, but community fuels momentum. Teachers didn’t just use CoGrader. They talked about it, shared it, and built trust around it. That social proof helped smooth the long sales cycles that often kill many EdTech startups.
3. Keep an experimental mindset. Markets shift, adoption patterns change, and assumptions break. The founders who win aren’t the ones with the perfect plan. They’re the ones who keep testing, learning, and adapting without losing speed.

For early-stage founders, especially in education, these aren’t abstract principles. They’re survival tactics. Build for pain you can feel, lean on the community to outlast slow sales, and keep iterating until the market meets you in the middle.

Conclusion

CoGrader’s journey is more than an EdTech story. It’s a founder’s playbook: solve a sharp pain point, sell it yourself, and keep adapting as the market shifts.

For early-stage founders, especially in education, the challenge isn’t moving fast. It’s staying close to the customer long enough to build trust and real product-market fit. Do that, and the leap from idea to traction becomes less of a gamble and more of a process.

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