Investing in Decagon: Rigor, Speed, and a New Concierge Model for Customer Experience

I first met Jesse Zhang in person last summer in Decagon’s San Francisco office. Instead of the usual pitch deck, Jesse showed up with two of his senior sales leaders and a pair of live cases they wanted to work through together. What followed was a focused, hands-on session that moved quickly from context to decisions and next steps.

That meeting was my first glimpse into how Jesse operates as a founder and CEO. He’s direct, execution-focused, and disciplined in his approach to problems. He moves quickly, but with attention to detail, and expects the same of the people around him. He’s big on what he calls “clock speed” – moving fast without lowering standards – and it shows up in how he runs meetings, sets priorities, and follows through.

Jesse’s co-founder, Ashwin Sreenivas, shares many of the same values. Like Jesse, he prioritizes high ambition and high velocity. The two share a similar background. Both grew up competing in math and science Olympiads. Both have already built and exited companies as solo founders – Jesse with Lowkey, a social gaming app acquired by Niantic, and Ashwin with the computer vision startup Helia, acquired by Scale AI – and they regularly draw on those past experiences as they build Decagon together.

When Jesse and Ashwin decided to work together, they didn’t start with a predetermined product idea. Instead, they spent months talking directly with operators – sending cold LinkedIn messages, interviewing hundreds of executives, and studying how service teams actually function day to day. Their goal was to understand where existing tools fall short and what could realistically be automated without compromising quality or trust. Those early conversations shaped Decagon’s product direction from the beginning and grounded it in real operational constraints.

Today, that approach shows up in how customers use and talk about the product. Teams at Affirm, Chime, Avis Budget Group, and Quince describe a platform that turns them into AI architects to deliver what Decagon calls concierge customer experiences at a global scale. Instead of relying on the old configuration-based paradigm, Decagon is creating a new paradigm that moves the world from customer relationship “management” to just giving customers the experience they rightly deserve. (You can read more about Decagon’s approach and technology here.)

While we’re still in the early innings of enterprise AI adoption, customer enthusiasm points to something much bigger. Customer service remains one of the largest and most entrenched software categories, with spend historically concentrated in legacy platforms built around ticketing and manual workflows. Salesforce Service Cloud alone generated over $8 billion in revenue in 2024. As companies push to improve both customer experience and efficiency, interest in AI-native systems that move beyond scripted automation continues to grow.

For Decagon, customer service is an entry point rather than an endpoint. The underlying technology supports a broader set of customer interactions, including proactive engagement. For example, Rippling is already using Decagon’s call insights and analytics to identify upsell opportunities with existing customers.

Turning a vision like that into a reality takes the right team. What we hear again and again from customers is what drew us to Decagon in the first place: this group is special. We are thrilled to co-lead Decagon’s $250 million Series D and to welcome Jesse, Ashwin, and their team to Index. The opportunity ahead is massive, and we love how they’re approaching it with rigor, humility, and a commitment to never stop learning.