Ep 159: Aaron Cannon Is Building the Leading AI Customer Research Platform; It's About to Upend a $140B Industry

Aaron Cannon is applying AI to solve one of the oldest and most important challenges in business: understanding exactly what customers want and need. Traditional consumer surveys often provide low-quality data, while one-on-one interviews are cost-prohibitive and not scalable. But AI unlocks profound new possibilities. How is Aaron using AI to conduct deep, insightful interactions at scale? What happens when organizations have always-on customer understanding? And what are the new opportunities for incorporating real-time feedback into product improvements?

Aaron Cannon is the co-founder and CEO of Outset, one of the fastest-growing, agent-led customer research platforms. Try it yourself here and help us improve American Optimist; we'll incorporate the top recommendations!

Prior, Aaron was the head of product at Untapped and Triplebyte and worked in senior product roles at Tesla, Pebble, and Monitor Deloitte. He launched Outset in 2022 after seeing an opportunity with large language models to fundamentally change how organizations learn from the people they serve. For this conversation, we're also joined by 8VC Partner Jack Moshkovich, who helped lead our investment in Outset.

We begin with Aaron’s path to founding Outset and the inefficiencies he saw in traditional customer research. Next, we explore how Outset’s AI-moderated interviews work in practice — from consumer studies to enterprise deployments at Microsoft, Google, and Uber. Learn how AI-led interviews can actually elicit more honest and in-depth responses than human-led conversations. Then, we dive into the explosive growth of the company — 8X revenue over the past year — and its “forward-deployed researchers" model. Finally, Aaron shares his vision for "self-driving research": AI that doesn’t just gather feedback but helps close the loop by identifying problems and even suggesting fixes — ultimately leading to improved products, experiences, and organizations.

00:00 Episode intro

01:10 Aaron’s entrepreneurial journey

06:00 How does AI-moderated research work?

09:25 Why people will talk to AI more than humans

13:40 How Outset landed Microsoft, Google & Uber

14:55 Are you replacing human jobs?

20:56 New possibilities for real-time product improvements

23:30 The pros and cons of synthetic research

28:00 Insane growth / how Outset 8X’d revenue

35:00 How AI is upending a $140B industry

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