This Entrepreneur Raised $231 Million To Build A Conversational AI Platform That Empowers Enterprises To Provide An AI-Driven Concierge Customer Experience

In the fast-paced world of startups, Jesse Zhang stands out as a thoughtful builder who has learned from experience and applied it repeatedly. A repeat founder, he has navigated the messy early days and experienced the adrenaline of product-market fit.

Jesse now leads Decagon, one of the world’s fastest-growing AI customer experience platforms. He has recently raised a $131M Series C round co-led by Andreessen Horowitz and Accel. In this exciting interview, he talks about the challenges he faced when things didn’t progress as planned.

Jesse also discusses the importance of resilience, his experiences with selecting an industry that is booming, and what it means to ride the wave.

Listen to the full podcast episode and review the transcript here.

Growing Up with Curiosity

Raised in the intellectually rich environment of Boulder, Colorado, Jesse found himself drawn to problem-solving at an early age. Having spent time on both the East and West Coasts, he considers the environment in Boulder to be very different, teaching people to be independent.

“I did a lot of math contests,” Jesse recalls. That analytical mindset led him to Harvard to study computer science, where his passion for real-world applications evolved into a fascination with startups. He enjoyed applying skills like reasoning and systematic thinking to real-world problems.

Jumping In Early And Learning Fast

Eager to build, Jesse graduated early from Harvard and dove headfirst into startup life. That first venture landed him in Y Combinator and eventually brought investment from Andreessen Horowitz. But the path wasn’t linear.

“Things didn’t go as planned,” Jesse admits. “We chased the wrong ideas. We went on wild goose chases based on our assumptions instead of customer feedback.” In retrospect, he realizes that getting experience from working in a great company would have been advisable.

Initially, Jesse’s approach to building companies was not necessarily centered around a specific idea. He had some great ideas, but also pivoted constantly while trying to achieve the ideal product-market fit and finding something that resonated with the audience.

Jesse now believes in keeping an open mind and basing strategies on real customer experiences. At that time, he simply kept pushing in the face of challenges. That’s something that every founder has related to at some point.

Lowkey: The First Venture

That first venture was Lowkey, a performance video capture platform for gamers. When playing games, users can capture videos, edit them, and host them. Although the monetization aspect wasn’t clear early on, traction came fast.

“We just focused on growth and user engagement,” Jesse says. The result? A successful acquisition by Niantic in 2021. Jesse credits timing and market fit for the outcome, but also recognizes the danger of letting hype, not signal, steer the journey.

“You really need to talk to customers, not just once, but constantly,” Jesse says. He also credits the fantastic team that helped build out the social pillar of the product. Niantic was an excellent fit for Lowkey. The company was interested in investing in acquisitions, and the situation was just right.

Building Smarter the Second Time

After the exit, Jesse and co-founder Ashwin Sreenivas set out to do things differently with Decagon. The guiding principle was to be radically customer-driven from day one.

“We didn’t go in with a fixed idea. We lined up a ton of conversations with large companies and let the use cases emerge from those,” Jesse explains. Their objective was to identify what users would pay real money for.

What emerged was a deep and pressing need for enterprise-grade AI agents for customer service. And Decagon was born. Allowing the process to direct their path helped the co-founders block out the noise and maintain a laser focus.

Decagon’s product is a fully autonomous digital worker that handles everything from booking changes to loyalty point inquiries over voice, chat, email, and more. It sits in front of the company’s support operation or call center and interacts directly with its customers.

“It’s about efficiency for the company, but also about delivering a better experience for the customer 24/7, in any language,” Jesse says. Their product eliminates mundane, repetitive tasks for humans, allowing the workforce to focus on more valuable tasks.

Early Signal, Fast Scale

The signal came fast. “We had zero revenue, and still some Fortune 500 companies were willing to sign six-figure contracts,” Jesse says. Since they were trendsetters, Jesse and Ashwin had some reservations about working with big companies as a two-person team.

It turned out that not only did the companies lack alternatives, but they also believed the Decagon approach was correct. Within six months, Decagon had crossed seven figures in revenue. The co-founders realized that there were enough customers who cared about what they were doing.

As Jesse points out, Decagon has an edge and can get large contracts since the ROI is very clear. Companies can make a reasonable justification for investing in AI here because they can see that this is not only about incurring those costs; it is also about realizing benefits.

It’s also about improving their customer experience, which ultimately drives more revenue. Then again, the larger the deal, the longer the process was, and the more complex it became.

At Decagon, they have the approach of building long-term partnerships with customers. Jesse believes in demonstrating that they are good at what they do and reliable. That’s something he has learned when navigating the organization.

Building a Strong Team and Company Culture

While on the subject of relationships, Jesse emphasizes the importance of building a strong team and fostering a great company culture. Following contracts with large companies, a rapid growth period ensued, marked by an over 500% increase in headcount within 12 months.

Jesse points out that they are mindful about culture. Decagon currently operates in an entirely in-person environment. Jesse is now bringing on some of the senior sales personnel, either remotely or at the New York office. This move has made it easier for the culture to assimilate.

Jesse believes in choosing and hiring the right people who improve the culture and elevate the team. At Decagon, they are entirely customer-centric, and employees must understand how they conduct business and be “empathetic and caring of the customers.”

Jesse also reveals that they have instituted a certain level of intensity when creating a culture that drives a great reputation. People at Decagon are hard workers who take pride in outworking anyone else. Yet another crucial aspect is clock speed.

Jesse calls it the speed at which people’s minds can move and adapt. Traditionally, companies have engineers as the brains of the organization, but at Decagon, they have genuinely smart people across the entire organization, including sales, marketing, and more.

That’s one of the things Jesse is most proud of in building the company.

Raising Funding for Decagon

Jesse reveals that they have raised a Series C round, which has brought Decagon’s total funding to $231M, with a valuation of $ 1.5B. The exponential interest in the market for products like the ones Decagon is building has contributed to its success, since they have executed it well.

With offers from many top-tier firms, Jesse stuck with those who had earned his trust: A16Z and Accel, both of whom had backed him before. These investors led Decagon’s seed round and series A round, respectively, and are currently doubling down.

Storytelling is everything that Jesse Zhang was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Peter Thiel, Silicon Valley legend (see it here), where the most critical slides are highlighted.

Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.

“In the early days, trust is everything,” Jesse says. “You want investors who will grind with you and not get in your way.” Jesse and Ashwin built great relationships with them, dating back to their last company.

Jesse concedes that at each growth stage and across the board, they are looking for people they can connect with and will benefit from the work they do at Decagon. He was keen on finding personalities they “genuinely liked and got along with.”

Decagon’s investors have brought valuable experience that has contributed to the company’s establishment and growth. Challenges never faze them, which has made Jesse and Ashwin happy to double down with their supporters.

Rethinking the AI Playbook

Decagon is now experiencing rapid growth, both in terms of customer base and headcount. The brand has established an excellent reputation, making customer acquisition and retention easier. Its product differentiation has also contributed significantly.

Decagon also has good speed differentiation, and its team is highly organized, allowing it to work effectively with customers. What makes Decagon different isn’t just its use of generative AI; it’s how it’s built. Jesse and Ashwin have adopted a unique approach that people empathize with.

“We developed an internal system we call AOPs or Agent Operating Procedures that are natural language-based and flexible,” Jesse explains. “That means non-technical users can configure and manage complex support flows without needing engineering resources.”

Jesse points out that, undoubtedly, there has been a lot of automation in their space earlier. For instance, contact centers, customer service, surveys, and customer experience that use chatbots and IVR. Then there are phone trees where callers select from a menu of options.

However, customers hate being put on hold and the delays in trying to connect with a human quickly. These issues have been addressed with the use of generative models, which enhance the customer experience.

Traditionally, the techniques used to build agents have been engineering-heavy, similar to the classic Salesforce playbook, where they’re trying to lock users into their language.

Its nontraditional approach gives Decagon a clear edge. It offers speed of deployment, adaptability, and reduced dependence on technical teams. Large workforces can quickly build and manage complex use cases, empowering the business and company.

Jesse is well aware that differentiation doesn’t last forever since competitors will eventually catch up. The key is to innovate constantly to maintain that edge and stay ahead of the curve.

The Long-Term Vision

Jesse envisions a world where every company, brand, and product has its own AI interface layer, as it can offer a significantly better and more efficient customer experience. He thinks that the very nature of customer experience is poised for a significant transformation.

More than just reactive support, Jesse sees these agents evolving into proactive companions or concierges that help users even before they ask. They process refunds and resolve basic issues since they can actually engage with customers.

AI agents can also interact with people before they become customers, introducing the new parts of the product and assisting with sales. Large organizations are now starting to recognize their AI agents as strategic differentiators for their own businesses.

They view it as a strategy to generate more revenue, rather than just a cost center where they’re trying to minimize their expenses. “It’s not just about replacing agents; it’s about rethinking what customer experience means,” Jesse says.

Advice to His Younger Self

Asked what he’d tell a younger version of himself, Jesse doesn’t hesitate: “Things work out if you just keep going. But be smart about how you spend your time. Don’t fall into the trap of building before you have real signal.”

Jesse believes in surrounding himself with good people and leaders who can come in and help with scaling the company. He spends a significant amount of time on the hiring side and leverages the expertise of other entrepreneurs and investors to help him choose the right team.

Final Thoughts

Jesse Zhang’s journey is one of thoughtful iteration and learning from the first company’s setbacks, taking the lessons, and building smarter the next time.

With Decagon, he’s proving that the combination of customer obsession, timing, product clarity, and a relentless team can turn a messy beginning into an exponential outcome.

Listen to the full podcast episode to know more, including:

• Jesse Zhang emphasizes starting startups with customer feedback, rather than fixed ideas, to avoid wasting time and effort.
• His first company, Lowkey, was acquired by Niantic after strong user growth, but it taught him the pitfalls of intuition-driven building.
• With Decagon, Jesse prioritized signal over hype, landing six-figure contracts before generating revenue.
• Decagon’s AI agents autonomously handle customer interactions, improving efficiency and experience across support channels.
• Jesse emphasizes the importance of selecting investors based on trust, drive, and long-term alignment.
• Building a fast-scaling team with a high “clock speed” culture has been key to Decagon’s execution and growth.
• His biggest advice: move fast, but only after deeply validating the problem and market with real customers.

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Keep in mind that storytelling is everything in fundraising. In this regard, for a winning pitch deck to help you, take a look at the template created by Peter Thiel, the Silicon Valley legend (see it here), which I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash. 

Remember to unlock for free the pitch deck template that founders worldwide are using to raise millions below.

 

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