Decagon's Jesse Zhang On Sales Battles, AI 'Wrapper' Revenge, And Making Agents Work

The CEO of $4.5B valued Decagon talks speed and sales in a hyper-competitive market, holding off OpenAI, and a new standard for AI agents on The Upstarts Podcast.

When it comes to calling customer support, startup CEO Jesse Zhang knows your pain.  ”It’s just a very frustrating experience, because you’re stuck in a loop,” he says.

In 2023, he and co-founder Ashwin Sreenivas launched Decagon to solve the problem with powerful new technology: AI agents. Today, customers like Avis Budget Group, Duolingo and Fanatics all work with Decagon, helping it reach a $4.5 billion valuation.

But as AI unlocks new possibilities in support, Zhang faces serious competition from more established and better-funded rivals. We’ve written about this race and how Sierra, led by former Salesforce co-CEO and OpenAI chairman Bret Taylor, has leaned on enterprise ties to carve out its own space in the market, alongside others like Intercom and Forethought, recently acquired by Zendesk.

And on The Upstarts Podcast, Zhang was candid about that competitive battle, sharing how Decagon values speed and “go-to-market execution” as “advantages,” but not “long-term differentiators.”

He also shared his take on why OpenAI and Anthropic won’t move in on Decagon’s business; how he’s using two layers of agents to solve customer problems through a system called Duet; and why he envisions this category moving from support to other conversations through an AI concierge.

Plus, he shares his Upstart Moment: how he and the team scrambled to win an uphill sales battle by converting “red dot” skeptics into “green dot” buyers.

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This season of The Upstarts Podcast is presented by Mercury.

Chapters:
00:00 Introduction
02:38 Why support was still a problem
05:34 Jesse Zhang’s founder story
15:23 Three pillars of startup strength
16:20 A 10x name and first customers
19:24 Winning with speed and scale
24:20 Jesse’s Upstart Moment in sales
31:35 Why you need to be 10x better
33:43 Revenge of the AI ‘wrapper’
37:17 Long-running agent ‘duets’
40:44 Your future concierge

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Just looking for the highlights? As always, we break down four top startup lessons from the episode for paid subscribers below. Unlock all of our paid posts by taking advantage of our first birthday sale: 25% off an annual subscription.

1. Three founder traits for a free-for-all

2. How to win hyper-competitive sales

3. How AI ‘wrappers’ can hold off the labs

4. Use agents to improve your agents