Launching oakpool.ai

Why we’re building for the AI Search era

Today, we’re introducing oakpool.ai, a sister company built to help brands understand how they show up inside generative search environments. This has been a long time coming. Link to Press Release Here.

Over the past year, it became obvious that the ground under digital marketing was shifting faster than most teams realized. A recent Adobe study found that 77% of U.S. ChatGPT users now treat it like a search engine and more than a quarter of Gen Z starts their search on ChatGPT before Google. That’s not a trend line. It’s a reset in how people form trust, discover products, and make decisions.

At oakpool, we’ve always built for durable systems and real-world outcomes. We work across consumer goods, outdoor performance, hospitality, technology, cultural institutions, and multi-brand operating groups. We’ve supported brands like Goslings Rum, GORE-TEX, Parlor Skis, Chittum Skiffs, Hydrolift, Zum, The Mina Foundation, Caesars Entertainment, Pandion Creative, MIT Sloan, and private holding companies like Chenmark and Beaumont Products. The variety has given us a clear view into how quickly search behavior is evolving and how hard it is for teams to track their presence across the new engines.

Generative engines aren’t ranking pages. They’re pattern-matching across the open web. They read sentiment, press signal, expert commentary, product clarity, documentation, awards, podcasts, reviews, and all the little traces a brand leaves behind. They reward evidence.

Most teams don’t know how they’re actually appearing inside these models. That’s the gap oakpool.ai fills.

oakpool.ai is the measurement layer and strategy engine for AI Search Visibility and Generative Engine Optimization. It gives brands a structured baseline on how often they surface in ChatGPT, Gemini, Claude, and Perplexity, and what those engines say. It shows where the gaps are and how to close them. And it pairs that with services built specifically for these engines.

• oakpool and oakpool.ai will operate side by side.
• oakpool continues to lead digital marketing, go-to-market builds, team design, and growth execution.
• oakpool.ai focuses on visibility, proof, and relevance inside generative search.

We’re fortunate to have a world-class advisory network around this work. People like Bharat Mediratta (former CTO of Dropbox and long-time Google engineering leader), Bardia Pourvakil (Co-Founder & CTO of GC AI), Carter Nicholas (IAS and DoubleClick), Alex Sandoval (Allie, Rappi), and Matthew Ford (IBM Innovation Consultant). They’ve shaped how we’re thinking about this shift, and continue to act as thought & strategy partners on the endeavor.

This is also our first in-house software plus services launch as a firm. Dan Zazworsky, our GM and Partner, and Grant Cowan, our Lead AI Consultant coming off Cornell’s internal AI programs, are driving the initiative with me.

The free visibility tool is live now at oakpool.ai. It gives any brand a simple starting point: here’s how you appear across the major engines, here’s which competitors are showing up, and why. From that starting point, we work with brands to create and implement a tailored AI Search Optimization strategy and deliver that alongside a real-time dashboard that gives clients visibility into how they are improving and what tasks our team is working on at any given time.

AI Search is becoming the front page of the internet. The brands that take it seriously now will be the ones still winning ten and twenty years from today. Our job is to help them get there.