Jesse Zhang On Raising $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’s latest venture, Decagon, has secured funding from top-tier investors like Andreessen Horowitz, A* and BOND Capital, Bain Capital Ventures, and Accel.

In this episode, you will learn:

• 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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About Jesse Zhang:

Jesse Zhang has a background in engineering (primarily web and AI/ML) and math. He studied Computer Science at Harvard and also interned at places such as Citadel, Google, HRT, Intel, Kensho, and EDO.

After college, Jesse founded Lowkey, a startup backed by Andreessen Horowitz and Y Combinator and acquired by Niantic at the end of 2021. Afterwards, he worked on the Social team at Niantic.

Jesse is also involved in some funds via Sequoia Scouts and Neo, and has started angel investing. Currently, he is working on a new company.

In his free time, Jesse likes writing math contest problems (like for the AMC 10 and AMC 8), playing basketball, watching tennis, playing board games, and certain video games (Grandmaster in Teamfight Tactics).

Connect with Jesse Zhang:

• LinkedIn
• Crunchbase
• JesseZhang.org
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty, hello everyone, and welcome to the DealMaker Show.

Jesse Zhang: Thank you.

Alejandro Cremades: Today we have with us an amazing founder — a repeat founder. We’re going to be talking about what it looks like when the journey doesn’t go as planned, and how to keep pushing. Also, how to think about picking markets and picking ideas.

Jesse Zhang: Thanks for having me.

Alejandro Cremades: They’re actually announcing a recent financing round. I think they’ve picked an industry that is really booming, and they’re definitely riding that wave. It’s going to be quite an exciting conversation — building, scaling, financing, exiting — all of the above. So brace yourself for a very inspiring conversation. Without further ado, let’s welcome our guest today, Jesse Zhang. Welcome to the show. So, originally born and raised in Boulder, Colorado — give us a walk down memory lane. What was life like growing up for you?

Jesse Zhang: Thanks for having me.

Yeah, I really liked growing up in Colorado. Boulder is a little bit of a separate environment from either of the coasts. I’ve spent time on the East Coast and the West Coast since then, and Boulder kind of feels like a whole different world. It’s quite nice — it allows you to be a bit more independent.

There are a lot of academic-minded people there, and it’s also just a beautiful place to grow up.

Alejandro Cremades: So tell us about getting into computers and problem solving, because you ultimately went to Harvard and studied computer science. What got you on that path?

Jesse Zhang: When I was little, I did a lot of math contests. That’s when I first started, and I really enjoyed doing math. I discovered what I was good at, and it was a good fit for what I wanted to do career-wise.

Once I got a bit older, I started looking into the applications of math, and computer science was one of the most obvious ones. A lot of my older friends at the time were interested in the same things — they were going into quant trading or startups. For me, startups seemed much more exciting.

You’re applying some of the same skills — reasoning, systematic thinking, and so on — but to real-world things. The real world is obviously messier, but you get to reap the benefits of any results you get.

Alejandro Cremades: Talking about results — you wanted results from college quite early. In fact, you graduated early so you could pursue your startup. Tell us about that.

Jesse Zhang: Yeah, at the time, it just felt like there was no time to waste. I had a great time in college. I met my wife there, made a lot of really good friendships, and just wanted to get going. So I graduated early to get started. At that time, I didn’t know anything about starting companies.

We actually did YC that year. It was a learning experience. There’s not really any way to learn it besides just trying it. We made a lot of mistakes and didn’t really know how to do many things.

In my opinion, when I talk to grads, I say that if you have enough desire or belief that you want to do it eventually, it’s just better to get into it.

If you feel like you’re not quite ready, then don’t rush it — try to get some experience first from a good company.

Alejandro Cremades: Why did you get so excited about this first company? What was it about the idea that made you feel like, “We’ve got to do this”?

Jesse Zhang: My approach to companies is that I don’t think you necessarily start with a specific idea in mind. That’s actually quite dangerous for most people. Sometimes it works out, but in general, it’s risky because before you actually start building, shipping, and having customers, you don’t have any signal on whether your idea is good. Maybe you think it’s good — but most of the time, it’s not.

We had some ideas, but the ideas kept changing because we realized they weren’t good. That’s been true in both companies. In my opinion, the best way to start is to have a very open mind and base your ideas on what you’re actually seeing from customers.

Alejandro Cremades: Now with this first company, you guys did the whole Y Combinator. You raised from Andreessen Horowitz. You really did the whole thing. However, you also experienced that things typically don’t go as planned. But you kept pushing. You kept going. What were some of the lessons that you took away from that?

Jesse Zhang: The biggest one is it’s super easy to get overexcited and start building in a direction that isn’t the right one. Or you don’t think things through and rely too much on your own intuition instead of customer experiences or real feedback.

That led us on a bunch of wild goose chases. We were building things and putting a lot of effort into it, working really hard — but at the end of the day, it wasn’t something that resonated with the market.

I’m sure every founder has experienced this at some point. It’s just part of the journey, and you have to get good at changing direction — or pivoting.

That was the biggest learning: you can’t overthink the first stage. You can’t make it too cerebral and try to solve the problem of “What is the right idea?” in a vacuum.

The only way to solve it is by getting as much signal as possible. You have to do the work, talk to customers, and really get into what people are willing to pay for — what they actually care about.

That was the biggest learning. And by the way, it’s a very common piece of advice, but it’s hard to know how deeply you need to do it until you try. Everyone knows you should talk to customers. But even after talking to customers, it’s easy to trick yourself into feeling like you’ve found an idea.

And then, six months or a year later, after grinding your butt off, you realize it was a waste of time.

Alejandro Cremades: With Loki — what were you guys ultimately doing? What was the monetization model?

Jesse Zhang: We were essentially doing performance video capture for video games. People were playing video games and having great digital experiences — especially during COVID when gaming really took off.

You could use Loki to capture videos, edit them, and host them. Honestly, monetization wasn’t top of mind at the time. It was all about getting users. We grew the user base quite fast, and that’s what mattered then.

What we’re doing now is very different. So if you’re starting out, you also have to keep in mind what kind of company you’re building. What are you optimizing for?

If you’re a consumer company, you’re probably not optimizing for revenue at the beginning. If you’re an enterprise SaaS company, then you probably are. You also have to know which style is the best fit for you.

Alejandro Cremades: Walk us through the M&A process too, because this was your first company and your first exit. That’s fantastic — the company was acquired by Niantic. How was that?

Jesse Zhang: Honestly, it was just a very lucky situation. It was the right timing — it was 2021, and a lot of companies were growing super quickly. Everyone was going aggressive on growth.

We hit it off with the team there. They have a fantastic team. We were brought in to build out the social pillar of their product.

It was a good fit, and they were in a place where they were willing to invest in M&A. It just worked out. If it had been a year later, with market shifts and different priorities, it probably would have been much harder. Timing and context matter a lot.

And I don’t think there’s a way to engineer outcomes like that.

Alejandro Cremades: I hear you. Now, you did the whole vesting with the company, but then you went at it again — with your latest venture. Walk us through the sequence of events. How did you think differently this time when it came to launching Decagon?

Jesse Zhang: The biggest thing I wanted to avoid was the mistakes from the first time — like wandering around for a long time trying different things. My co-founder Ashwin and I have very similar approaches to startups and life in general.

We decided to be super customer-driven. We lined up a bunch of conversations, mostly with large companies, and got to the bottom of what use cases they’d actually pay real money for. These were mostly around AI and AI agents.

But we didn’t go in with any preconceived notion of which space or use case would be best. We let the process decide. I’d highly recommend that approach — it helps you block out the noise, both positive and negative.

There’s often hype around a space, and you can get sucked into that without any customer demand. Or, conversely, there might be customer demand, but the narrative in the market is that it’s too competitive or not promising.

You have to think from first principles and decide for yourself. This process helped us do that, and it got us off the ground a lot faster.

Alejandro Cremades: For the people listening — what is Decagon?

Jesse Zhang: Decagon is an AI customer service agent — a fully autonomous digital worker that can sit in front of any customer support operation, contact center, or whatever, and talk directly with users.

This can be over phone, live chat, email — anything. For example, we’re working with a big hotel chain where users can book rooms, adjust reservations, upgrade, or ask about loyalty points.

The AI can handle all that autonomously. It doesn’t need to be handled by human workers since it’s repeatable and mundane. This drives efficiency for customers, letting their workforce focus on higher-value tasks.

And it’s a much better customer experience — you get what you want immediately, 24/7, in any language. That’s what we do.

Alejandro Cremades: What was the moment in the journey when you realized, “I think we’ve hit a nerve here”?

Jesse Zhang: Pretty early on, actually. We had fairly large customers willing to work with us on real, six-figure contracts — and we had zero revenue at the time.

We were like, “Oh crap, this is awesome.”

We still had some reservations — like, “Why can’t someone else do this?” — but that kind of signal was enough. When big companies are willing to work with just two people, that says something.

Jesse Zhang: And so it really goes to show that either they didn’t have a great alternative at the time or they really believed that our approach was correct. So we just kept going from there. And it was probably around the six-month mark, when we had crossed seven figures in revenue, that we realized — yeah, there are definitely enough customers who care about what we’re doing.

Alejandro Cremades: How was it like closing that first seven-figure deal?

Jesse Zhang: Oh yeah, that was great. That came a little bit later. I think the nice thing about our space is that you can get larger deals, and the ROI is very clear. Companies can make a very reasonable justification for investing in AI here because they can see — hey, this isn’t just saving costs; it’s improving the customer experience, it’s driving more revenue, and so on.

That’s what happened for us. And yeah, the larger the deal, the longer the process, and the more complexity there is. I think we’ve learned a lot over the short time we’ve been building this company — how to navigate organizations, how to show people why we’re good, why we’re reliable, and how to build good relationships. I think our customers appreciate the long-term partnership approach we take.

So yeah, it’s been a good learning experience.

Alejandro Cremades: I mean, talking about relationships and people — let’s talk about employees. If I take a look at LinkedIn and the insights, you guys have grown the team by over 500% in the last 12 months. That’s tremendous.

I’m sure the real number might be a little more or a little less, but let’s agree — this is crazy growth.

How do you go about growing that fast when it comes to people — and making sure you’re not breaking things culturally?

Jesse Zhang: Yeah, it’s not easy. We’re pretty mindful about culture. We currently have a fully in-person environment, though we’re now bringing on some senior folks on the sales side remotely. We have a New York office now too, so it’s starting to expand. But people spend a lot of time together, and that’s been really helpful. Being in person makes it easier for the culture to take root.

And part of culture is choosing the right people. Are you hiring people who improve the culture and elevate the team?

The tenets of our culture are:

First, we’re super customer-focused. We want people with that DNA — people who get it, who know we’re running a business. And to do that well, you have to be very empathetic and caring toward customers.

Second is a certain level of intensity. We’ve created a culture — and built a reputation — where people here are hard workers. We take pride in that. We’re going to outwork anyone.

Finally, we care about clock speed — how fast people’s minds can move and adapt. We have a lot of really smart people across the organization. Traditionally, you think of engineers as the brains of the org, but we want genuinely smart people in every department — sales, marketing, and so on.

That’s something I’m really proud of as we build the company.

Alejandro Cremades: Let’s talk about investment. You’ve raised quite a bit of money, and in fact, you’re announcing something exciting today — quite the round. Walk us through that.

Jesse Zhang: Yeah, so it’s a Series C. It’s co-led by a16z and Accel, at a $1.31 billion valuation.

As you said, we just announced it. Things are moving very quickly, and this brings our total funding to about $231 million. It’s an exciting time. There’s so much market interest right now for products like this, and so far, we’ve been executing pretty well — knock on wood that it continues.

We’ve built great relationships with our investors. a16z led our seed round, Accel led our Series A, and both are doubling down. My last company didn’t get to Series C, so this is a great experience. It really sets us up with the resources to continue growing.

Alejandro Cremades: Having already exited a company, and now building in one of the most exciting and hyped industries, you could have chosen any investor for this journey.

Why did you choose Accel and Andreessen? Why them, and not someone else?

Jesse Zhang: Good question. I’d say what you optimize for changes over time. In the early days, you’re optimizing mostly for trust. You don’t really know what’s going to happen yet. You might not even know what you’re working on. So you want someone who has high trust, who’ll stick with you when things aren’t going well, and who won’t be a net negative — like distracting you or sucking up your time.

We had a relationship with a16z. They backed my last company, and my co-founder Ashwin was close with them too. So there was already a high level of trust there, and the partners we’re working with really hustle. They get it, they grind, and they do a lot for us.

Same story with our Series A — Ivan at Accel, who I’d worked with before. At each stage, you’re looking for something different, but across the board, we just want to work with people we genuinely like. If they benefit from our hard work, we’re happy — and vice versa. They’re willing to put in the time too.

Same thing with our Series B. We’re working with Arif at Bain. He’s amazing. Personality-wise, we were really careful to find someone we genuinely like and get along with. He’s a successful entrepreneur and just very even-keeled. He brings a lot of experience and helps us with company building. He never freaks out or gets bothered. We love that.

So in the latest round, we already felt good about the folks around the table. We brought in a few new investors as well, but we were also happy to double down with the people who’ve been supporting us.

Alejandro Cremades: Tell us about the current state of Decagon. What’s the product like today?

Jesse Zhang: As you mentioned, we’re growing quickly — on both the customer side and the headcount side. Right now, we’re in a phase of just growth, growth, growth. We need to scale out what we have. And things are working pretty well.

What we’re known for in the market — and why customers enjoy working with us — comes down to two things: one, in my opinion, we have the best product and strong product differentiation. And two, we have speed differentiation — our team is just on top of things and works really well with customers.

We’ve taken a new approach to building AI agents — one that’s a lot more friendly for non-technical users.

If you look at our space — contact centers, customer service, and customer experience — there’s been a lot of automation in the past: chatbots, IVRs, phone trees. Everyone hates those. We’ve all been on hold, trying to get to a human.

What makes this new generation different?

One, generative models improve the experience.

But more importantly, we saw that most people in the industry still use older, engineering-heavy methods to build these agents. It’s the classic Salesforce playbook — lock you into their stack.

We came at it from a different angle. We developed a system we call AOPs — agent operating procedures — that are more flexible and based in natural language. That makes it easier for large teams to manage complex use cases.

It empowers business users to move faster. And in my opinion, if you’re building in the AI space, your differentiation needs to be on the product side.

Of course, those advantages don’t last forever. Other people will catch up. But it’s your job to keep staying ahead.

Alejandro Cremades: Speaking of staying ahead — imagine you go to sleep tonight and wake up in a world where the vision of Decagon is fully realized. What does that world look like?

Jesse Zhang: On one hand, I think the nature of customer experience will completely change. Every brand and product with users will have an AI agent interfacing with customers. It’s a better experience — more efficient. You’ll be at a disadvantage if you don’t have that.

But I also think the definition of customer experience will broaden. We’re already seeing that with our customers.

When you have a good AI system, it can do more than just answer questions or process refunds. It can actually engage customers, be proactive instead of reactive.

It’s more than just basic support — it can become a companion or a concierge. It can help customers before they even become customers. It can introduce new product features, offer suggestions, and so on.

So I think there’s massive upside for large organizations. They’ll stop seeing contact centers as just cost centers, and instead view them as strategic differentiators and sources of revenue.

Alejandro Cremades: Let’s shift to the past, with a lens of reflection. Imagine I put you in a time machine and bring you back to when you were graduating early from Harvard to start your first company. If you could stop that younger self and give one piece of advice before launching a business, what would it be and why?

Jesse Zhang: At a high level — and this is difficult — but things work out if you just keep going.

The second piece would be what we talked about earlier: be much smarter about how you spend your time in the early days. It’s so easy to fall into traps and waste time.

So I’d probably say: take a deep breath. Make sure you’re getting real signal from customers before diving in headfirst.

Alejandro Cremades: One final question — with all this growth, how do you keep up as a founder so you’re not outpaced by the speed of the company?

Jesse Zhang: A big part of it is surrounding yourself with really good people. Everyone — including Ashwin and me — has weaknesses. We help balance each other out.

But as things grow, there are just way more things to do. Neither of us has scaled an org to a thousand people before. So we need the right people — especially the right leaders — to come in and help.

The best way to scale is by getting the leadership hires right.

That means spending a lot of time on hiring and really leveraging others — like entrepreneurs who’ve done it before or your investors — to help you choose the right people.

Alejandro Cremades: I love it. Jesse, for the people listening who’d like to say hi or learn more about Decagon, what’s the best way for them to do so?

Jesse Zhang: Just go to our website. We have a brand new site up — Decagon.ai. There are plenty of ways to get in touch there.

Alejandro Cremades: Amazing. Jesse, thank you so much for being on the DealMaker Show today. It’s been an absolute honor to have you with us.

Jesse Zhang: Awesome. Thanks so much for having me.

*****

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