Invest Like the Best with Patrick O'Shaughnessy
Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]
06 Oct 2025
My guest today is Jesse Zhang. Jesse is the co-founder and CEO of Decagon, one of the fastest-growing AI customer service companies. Decagon provides a centralized AI engine to auto-resolve issues at any time, in every language, and across every channel. Jesse shares his systematic approach to finding product-market fit by asking potential customers exactly how much they'd pay for solutions. We explore why customer service and coding have emerged as the two clearest AI use cases for enterprises, and the key business and technical factors behind Decagon's momentum. We discuss the intense competitive dynamics of building in AI today, strategic decisions around building proprietary models, and deploying AI agents at enterprise scale. Please enjoy my conversation with Jesse Zhang. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:49) Building a Company in a Competitive Market (00:07:26) Personal Background and Competitive Upbringing (00:10:32) Challenges and Lessons from Previous Ventures (00:12:21) Ideation and Customer Discovery Process (00:19:31) Developing and Refining AI Customer Service Agents (00:32:26) Voice AI and Future Prospects (00:38:20) Utilizing Customer Interaction Data (00:39:59) Frameworks for Implementing AI in Business (00:41:48) Evaluating the ROI of Coding Agents (00:42:53) The Future of Company Agents (00:45:15) Brand Personality in AI Agents (00:47:48) Investor Interest in AI Companies (00:54:32) The Competitive Landscape of AI Talent (00:57:21) Building Proprietary AI Models (01:10:36) Customer Qualification and Engagement (01:17:27) The Kindest Thing
Full Episode
The best operators have a relentless focus on leverage, finding ways to multiply their impact rather than just working harder. But here's what I see happening in finance teams everywhere. Brilliant people getting buried in expense management busywork. If you think about it, you become a finance leader because you love strategic work.
modeling scenarios, optimizing capital allocation, finding the insights that actually move the business forward. But instead, you're chasing receipts and categorizing transactions. It's the opposite of leverage. This is exactly why I'm so bullish on what the team at Ramp has built.
Kareem and Eric understood that every minute spent on manual expense management is a minute stolen from high leverage work. So they automated all of it. Automatic categorization, receipt matching, spending controls that actually work. Check out ramp.com slash invest and see what happens when you eliminate the busy work. Cards issued by Sutton Bank, member FDIC. Terms and conditions apply.
To me, Ridgeline isn't just a software provider, it's a true partner in innovation. They're redefining what's possible in asset management technology, helping firms scale faster, operate smarter, and stay ahead of the curve. I want to share a real-world example of how they're making a difference. Let me introduce you to Brian.
Brian, please introduce yourself and tell us a bit about your role. My name is Brian Strang. I'm the Technical Operations Lead, and I work at Congress Asset Management.
How would you describe your experience working with Ridgeline?
Ridgeline is a technology partner, not a software vendor, and the people really care. I get sales calls all the time and I ignore them. Ridgeline sold me very quickly. We went from 7 billion to 23 billion and the goal is 50 billion. Ridgeline was the clear front runner to help us scale. In your view, what most distinguishes Ridgeline? They reimagined how this industry should work.
It was obvious that they were operating on another level.
It's worth reaching out to Ridgeline to see what the unlock can be for your firm. Visit RidgelineApps.com to schedule a demo. One of the hardest parts of investing is seeing what's shifting before everyone else does. AlphaSense is helping investors do exactly that.
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