I’m obsessed with validating product-market fit before writing a single line of code. Studying Ryan Glasgow’s journey as founder and CEO of UserLeap — a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster — sharpened my own playbook for testing demand early and de-risking execution.
Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat). That operating rigor shows up in how he navigated the pre-build phase — a period I pay particular attention to when coaching teams through product discovery.
I rewind the clock to the 6-month period before launch, when I’m validating the idea and assessing a crowded market. This is where segmentation and early customer conversations do the heavy lifting. I make the target user painfully specific, probe for desired outcomes, and pressure-test willingness to pay. Just as importantly, I avoid common product/market fit mistakes: over-indexing on feature requests, conflating enthusiasm with intent, and skipping a clear hypothesis about the job-to-be-done.
From there, I frame the first version of the product as the smallest coherent solution that proves the value thesis. I outline how to think about adding new features — through evidence-based prioritization, not wishlist drift — and how UserLeap’s 3 product principles can guide day-to-day product decisions so the roadmap compounds rather than sprawls.
As a self-described “product guy,” I taught myself founder-led sales, including the specific tactics that made the biggest difference and how I’ve refined my approach into a repeatable playbook. That means running tightly scoped discovery calls, qualifying ruthlessly, using problem-centric demos, and turning every objection into a testable learning.
There’s also a simple question I always ask in customer meetings that unlocks clarity: “What would make this an absolute no-brainer for you in the next 30 days?” It anchors the conversation in outcomes, timelines, and trade-offs — the raw material for reliable product-market fit signals.
For the curious builders, here are the books that have most influenced my approach to product discovery, roadmapping, and founder-led GTM: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services by Anthony Ulwick; You Can’t Teach a Kid to Ride a Bike at a Seminar by David Sandler; and User Story Mapping: Discover the Whole Story, Build the Right Product by Jeff Patton.
You can follow Ryan on Twitter at @ryanglasgow.
If you’re navigating product-market fit right now, use these tactics to sharpen segmentation, run higher-signal customer conversations, and build a first version that earns traction fast — then scale with a repeatable founder-led GTM motion.
Inspired by this post on First Round.
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