The $50 Vertical Intelligence Revolution: How Flatfile Industrialized Pain-Based Segmentation

When Jordan first encountered David Boscovic at SaaStr and heard about Flatfile's AI-powered go-to-market system, he was immediately intrigued. As someone who's typically skeptical of "agentic" solutions that promise the world but deliver black boxes with zero observability, Jordan found himself genuinely excited about what Flatfile had built. Doug, meanwhile, had been predicting exactly this kind of evolution for months: companies that would systematize pain-based segmentation at enterprise scale.

When David joined us as a spot guest on our live stream (Doug was traveling through Germany at the time), we realized something profound: Flatfile has industrialized the core principles of the Cannonball GTM methodology at a scale that would make even the most ambitious growth hacker weep with joy.

What Flatfile has accomplished represents the natural evolution of pain-based segmentation, from manual implementation using prompts and elbow grease to a systematic, AI-powered machine that can simultaneously discover and exploit existential data points across hundreds of verticals.

And here's the kicker: they're doing it for roughly $50 per vertical.

The Cannabis Revelation: When $50 Beats Months of MBA Intern Work

Let us tell you about David's weekend cabin experiment, which changed everything for Flatfile's go-to-market strategy.

Picture this: David and his technical chief of staff, Leon, holed up in a cabin north of San Francisco for 48 hours, surviving on maybe four hours of sleep total. Their mission? See if they could use ChatGPT's new deep research capability to automate what previously required months of expensive consultant work.

They started with field services, a vertical they thought they understood. Within 30 minutes and a few dollars in AI tokens, they had a 40-page report that was so accurate and insightful that when David shared it with CEOs in that market (without telling them it was AI-generated), their response was: "David, where did you find this? We learned things we didn't know about our own industry."

But the real breakthrough came when they applied this to cannabis retail, a vertical where traditional ICP approaches had failed them spectacularly.