Behind the curtain of a $4.5b AI-native powerhouse
Ashwin Sreenivas · Co-founder, Decagon
Ashwin Sreenivas spent his childhood in India waking up at 5am and studying until 8:30 at night. History, geography, physics, chemistry, math. Every day, from 4th grade through 12th grade, through the Olympiads and the National Talent Search Exam. He says now, three years into building one of the most exciting AI-native companies in the world, that all of that is precisely why what he does today feels almost easy. “I get to come in here and there’s a lot of people and I’m having fun.”
That mode is what Decagon runs on. The company Ashwin co-founded with Jesse Zhang in 2023 is now valued at $4.5 billion, has crossed 450 employees in three years, and works with some of the largest enterprises on the planet. The path there has in some ways been simple: don’t theorize about where AI is going, talk to customers until the pain is unmistakable, build for that, ship, repeat. Decagon went from zero to $1 million in ARR with two co-founders and no employees.
In this conversation, Ashwin walks through what that means in practice. How Decagon operationalizes a single cultural priority: speed, even when it costs coordination. How they hire 450 people without breaking the bar. How AI has reshaped the IC engineer, the AE, and the VP of EPD. And why, after a year of running 6+ days a week, the thing he and Jesse would tell their earlier selves is: go faster.
Ashwin Sreenivas is the co-founder and CTO of Decagon, the AI customer concierge platform founded in 2023 that serves enterprise customers including Substack, Eventbrite, Duolingo, and Notion and is valued at $4.5 billion. Decagon Labs, the company’s in-house model development effort, now powers around 90% of Decagon’s model traffic. Before Decagon, Sreenivas co-founded Helia in 2019, an AI startup acquired by Scale AI a year later. He started his career as a strategist at Palantir Technologies in New York. Sreenivas holds a Bachelor’s degree (2017) and Master’s degree (2019) in Computer Science from Stanford University. Decagon raised $35M in 2024 and has scaled to over 450 employees.
The most quotable moments from Ashwin Sreenivas
In the early days, all we did was say the only thing that matters is what customers care about and what they're willing to pay for today. Everything else is downstream of that.
Great market, bad founder — market wins. Bad market, great founder — market wins. If you pick the right market, it will pull the problem and product out of the founding team.
You have to give somewhere, and we gave for speed. The pace of building has changed so quickly with AI: if it's two days instead of two weeks, there isn't that much time for coordination.
Use all the tools you have, but at the end of the day you are responsible for the code you push, and you should be prepared to defend it — not say 'the AI agent wrote it, that's all I know.'
Don't over-intellectualize, and listen to your customer. If you build something your customers care about, you can mess up everything else and it doesn't matter. Do everything else right but build something nobody cares about, and nothing else matters.
Every fast-growing company, probably without exception, has had a thousand fires internally. As you grow quickly in competitive markets, things are bound to go wrong. That's just how it is.
The red flag is that gut feeling of something being a little off. Every single time I've ignored it and tried to be clinical and objective, I have regretted that hire.