The Idea: Jesse Zhang graduated from Harvard in 2018 and founded Lowkey, a gaming clip-sharing app that was eventually acquired by Niantic. It was during that first startup journey - manually handling customer support as a two-person team with no real tooling - that he built a deep empathy for just how broken the support experience was. When GPT-4 arrived and large language models suddenly became capable of genuine reasoning, Jesse saw the opportunity clearly. He teamed up with Ashwin Sreenivas, a Stanford CS grad who had previously founded Helia (sold to Scale AI), and the two met at an Andreessen Horowitz retreat in Utah where they started canvassing large companies about where AI could deliver real value. Customer support kept coming up. Every company was drowning in tickets, burning cash on BPOs, and watching customer satisfaction scores crater. This was the beginning of Decagon.

The Execution:

• August 2023: Jesse and Ashwin found Decagon with a simple thesis - enterprises don't need another chatbot, they need an AI agent that can actually reason through complex customer problems and take action on their behalf.
• June 2024: Decagon emerges from stealth with $35M in combined seed and Series A funding, already counting Duolingo, Notion, Rippling, and Eventbrite as customers. The round drew 5x more investor demand than capacity.
• October 2024: Decagon raises a $65M Series B led by Bain Capital Ventures, quadrupling its valuation in just a few months. Bilt reports that Decagon is handling 70% of their 60,000 monthly tickets, saving hundreds of thousands of dollars a month.
• February 2025: Decagon launches its Voice channel in partnership with ElevenLabs, extending AI-driven support to phone interactions - moving from chat and email into the call center itself.
• June 2025: A $131M Series C co-led by Andreessen Horowitz and Accel values Decagon at $1.5B - unicorn status in under two years. Chime reports a 60%+ reduction in contact center costs and a doubled Net Promoter Score after deploying Decagon's agents.
• November 2025: Deutsche Telekom announces a commercial pilot with Decagon alongside a strategic investment from T.Capital, signalling the company's push into global enterprise and telco.
• January 2026: Decagon closes a $250M Series D led by Coatue and Index Ventures, tripling its valuation to $4.5B. The company now serves 100+ enterprise customers including Avis Budget Group, Block, and Deutsche Telekom.

The lesson? Jesse and Ashwin were told not to enter the customer support space - too crowded, too much AI hype, too many fancy demos. They entered anyway because they saw something others missed: enterprises didn't need a better chatbot, they needed an AI agent they could actually trust. By obsessing over measurable outcomes, building transparency into every decision the AI made, and signing six-figure contracts before they had a full team, they turned the most boring category in software into a $4.5B company in 24 months. The market doesn't reward the first mover. It rewards the one who makes it work.