How Outset Turned AI Interviews Into a New Category

Outset (YC W23) is building an AI customer research platform used by companies like Google, Microsoft, and Nestlé. Its AI interviewers have now conducted millions of conversations, giving companies the scale and speed of a survey with the depth of a one-on-one interview. In this founder fireside, Outset co-founder and CEO Aaron Cannon sits down with YC's Harj Taggar to talk about building a product before the market was ready for it, how they helped create the category of AI-moderated research, and what comes next. Aaron shares how they're expanding beyond interviews with Outset's new Simulations Lab and Digital Twins, which let companies simulate their customers and get feedback on everything from messaging and pricing to new products. Apply to Y Combinator: https://www.ycombinator.com/apply Work at a startup: https://www.ycombinator.com/jobs Chapters: 00:00 — Intro 00:24 — What Outset Does 01:18 — Building a Category Before the Market Was Ready 06:31 — Landing the First Enterprise Customer 08:14 — How Better AI Models Changed the Product 12:57 — When the Market Finally Caught Up 14:45 — From AI Interviews to Customer Simulations 19:40 — Aaron’s Path to Becoming a Founder

Harj TaggarhostAaron Cannonguest

Aug 27, 202621mWatch on YouTube ↗

EPISODE INFO

Released: August 27, 2026
Duration: 21m
Channel: YC Root Access
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Outset (YC W23) is building an AI customer research platform used by companies like Google, Microsoft, and Nestlé. Its AI interviewers have now conducted millions of conversations, giving companies the scale and speed of a survey with the depth of a one-on-one interview. In this founder fireside, Outset co-founder and CEO Aaron Cannon sits down with YC's Harj Taggar to talk about building a product before the market was ready for it, how they helped create the category of AI-moderated research, and what comes next. Aaron shares how they're expanding beyond interviews with Outset's new Simulations Lab and Digital Twins, which let companies simulate their customers and get feedback on everything from messaging and pricing to new products. Apply to Y Combinator: https://www.ycombinator.com/apply Work at a startup: https://www.ycombinator.com/jobs Chapters: 00:00 — Intro 00:24 — What Outset Does 01:18 — Building a Category Before the Market Was Ready 06:31 — Landing the First Enterprise Customer 08:14 — How Better AI Models Changed the Product 12:57 — When the Market Finally Caught Up 14:45 — From AI Interviews to Customer Simulations 19:40 — Aaron’s Path to Becoming a Founder

SPEAKERS

Harj Taggar
host
Partner at Y Combinator and interviewer on YC’s Root Access.
Aaron Cannon
guest
Co-founder and CEO of Outset, previously head of product at Triplebyte.

EPISODE SUMMARY

In this episode of YC Root Access, featuring Harj Taggar and Aaron Cannon, How Outset Turned AI Interviews Into a New Category explores outset created AI-led customer interviews, then evolved into digital twins. Outset is an AI customer research platform that conducts human conversations at scale and then synthesizes results into actionable insights.

RELATED EPISODES