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20VC Insight
Zhang: Backward compatibility creates baggage for legacy SaaS in AI era
“Having the older way of doing things actually serves as baggage because you have so many customers already locked into that approach. And because you have a lot of customers, anything you build has to be compatible with all of them. And so it just always inher…”
Jesse Zhang Sep 19, 2025 ▶ 16:41 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Assertion Not checkable as stated
Zhang: Enterprise human labor budgets are 10x larger than software spend
“Human labor is generally like an order of magnitude larger than software spend, like 10 X or more.”
Jesse Zhang Sep 19, 2025 ▶ 21:44 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Disclosure
Zhang: Decagon clients spend more on AI agents than CRM software
“And so if you look at a lot of our customers, for example, they're spending more on the AI agent Than the previous CRM software for support.”
Jesse Zhang Sep 19, 2025 ▶ 22:07 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Prediction Open · timeframe Sep 2030
Zhang: AI customer service resolution will reach 80% to 90% soon
“I think in three to five years, it'll probably creep towards like just consistently 80 to 90, right? Because you're able to just so easily allow the end users to capture more logic and teach you new things.”
Jesse Zhang Sep 19, 2025 ▶ 24:01 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Assertion Not checkable as stated
Zhang: Very few enterprises build AI customer support fully in-house
“I would say from our experience so far, very few people will build it themselves.”
Jesse Zhang Sep 19, 2025 ▶ 29:50 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Assertion Not checkable as stated
Zhang: Approximately 50% of Decagon's new code is AI generated
“Yeah, roughly there. The lines get blurred because oftentimes what will happen is like, hey, I'm sitting down to do this project. Let me just have the agent Take a stab at it first, and then you go in and like edit things and move things around. So there's a b…”
Jesse Zhang Sep 19, 2025 ▶ 31:07 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Opinion
Zhang: In-person work is significantly more productive than remote work
“It's just way more productive. My last company, we were remote, so because it was during COVID, and I think there's pros and cons of that, but I think overall, just personality-wise, it just comes down to the founder's personalities. Like, Ashwin and I are doi…”
Jesse Zhang Sep 19, 2025 ▶ 32:41 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Disclosure
Decagon rejected funding offers up to 2x higher than $1.5B
“I will say we could have raised at a much higher valuation up to like 1.5 to two X.”
Jesse Zhang Sep 19, 2025 ▶ 36:08 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Prediction Open · timeframe Sep 2030
Zhang: Enterprise AI customer experience market will have multiple winners
“I think our space probably will have multiple winners, hopefully not too many, and hopefully we're one of them. I think it's just hard to say, like, why there would be a huge single winner here. The reason is that there's not that many network effects from bet…”
Jesse Zhang Sep 19, 2025 ▶ 38:15 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Insight
Zhang: Decagon prioritizes raw clock speed over experience across all roles
“Technically we really value just like clock speed really, really highly. And clock speed, I just mean like how fast your brain works and how fast you can learn. And this is across all functions, right? Obviously it's important for engineering, but for Sales an…”
Jesse Zhang Sep 19, 2025 ▶ 41:06 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
20VC Insight
Zhang: Product-first approaches outperform forward-deployed engineering in consistent enterprise software
“And so, I think our mistake was we over-indexed on that a little bit. Because I don't think that concept necessarily makes sense in all use cases. And in our use case, the types of things that people care about across different customers is generally pretty co…”
Jesse Zhang Sep 19, 2025 ▶ 44:06 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
NO PRIORS Assertion Supported
Zhang: Decagon cuts enterprise contact center costs by 60% to 70%
“And we've done case studies now where, you know, folks have been able to cut that down by, you know, 60, 70%.”
Jesse Zhang Sep 18, 2025 ▶ 3:05 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Disclosure
Zhang: Decagon prioritizes raw intelligence over direct experience across all roles
“We're generally just selecting for very smart people. First of all, I think we care more about that than like, you know, direct experience and so on.”
Jesse Zhang Sep 18, 2025 ▶ 6:02 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Disclosure
Zhang: Decagon mandates five days in-office, with many working weekends voluntarily
“We're five days and then a lot of folks come in on the weekends, but it's not like a requirement.”
Jesse Zhang Sep 18, 2025 ▶ 7:19 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Opinion
Zhang: All successful AI companies share heavy in-office cultures
“I think pretty much all the AI companies that are doing well have, you know, pretty heavy in office cultures. It's just, you get way more done, especially, especially in the early stage.”
Jesse Zhang Sep 18, 2025 ▶ 7:53 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Insight
Zhang: Aspiring founders learn more at post-PMF startups than pre-PMF companies
“Generally, when I talk to engineers that want to join startups, for example, and let's say they eventually want to start their own company, which is a very common profile, it's, in my opinion, it's like way more useful to join somewhere where they've already k…”
Jesse Zhang Sep 18, 2025 ▶ 11:39 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Prediction Not checkable as stated
Zhang: Foundation model labs will target consumer applications before enterprise software
“I think it makes a lot of sense for them to push into application layer, and I think they will. In terms of what applications, I mean, generally they'll probably start with applications where it's more consumer prosumer-y because there's, it's just more self-c…”
Jesse Zhang Sep 18, 2025 ▶ 18:37 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Prediction Not checkable as stated
Zhang: AI labs will target coding before customer service
“I think before they tackle our space, there will probably be other spaces they have to tackle first. Yeah. Coding's probably one of them.”
Jesse Zhang Sep 18, 2025 ▶ 19:30 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Opinion
Zhang: Salesforce's configuration-heavy SaaS model is wrong for the AI era
“Again, obviously, we respect like the sales forces of the world that build amazing businesses, but we just don't think that's the right approach for the AI era.”
Jesse Zhang Sep 18, 2025 ▶ 21:54 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Prediction Not checkable as stated
Zhang: AI agent industry will shift toward output-based pricing
“And we'll probably start seeing that more and more in the AI agent space where you generally price per like the output that that's doing. I think that that works. I think that's just very clearly the right pricing model for our space”
Jesse Zhang Sep 18, 2025 ▶ 23:40 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Prediction Not checkable as stated
Zhang: Consumers Will Interact With Agents Over Apps and Websites
“And eventually, if it's good enough, most consumers will just interact with the agent instead of even logging into the mobile app or the website.”
Jesse Zhang Sep 18, 2025 ▶ 25:46 No Priors Ep. 132 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Assertion Supported
Decagon AI saved Bilt Rewards 65 support agent headcounts in one year
“Now basically we're almost, almost a year in at this point, they've been able to really restructure their customer support team. And again, we published a case study on this where they were able to quantify like, okay, what are the savings? Right. And so, so f…”
Jesse Zhang Jan 16, 2025 ▶ 7:18 No Priors Ep. 97 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Insight
Zhang: Instruction following matters more than reasoning for customer service AI
“And for us, actually those things help, but they're actually not the biggest difference maker. So in our use case, the type of intelligence that matters the most We would probably describe it as instruction following.”
Jesse Zhang Jan 16, 2025 ▶ 11:07 No Priors Ep. 97 | With Decagon CEO and Co-Founder Jesse Zhang
NO PRIORS Insight
Zhang: Viable AI agent use cases require incremental value and quantifiable ROI
“The use cases that emerged, like you have to have those two qualities. Like it has to be able to be something that can be rolled out slowly and doesn't have the perfect off the bat, but it's already providing value, right? Like I think coding agents is like a …”
Jesse Zhang Jan 16, 2025 ▶ 28:57 No Priors Ep. 97 | With Decagon CEO and Co-Founder Jesse Zhang
a16z Prediction Not checkable as stated
Zhang: Enterprise adoption of open-source AI will take longer than expected
“I think they'll get there, but it'll probably take longer than people think because, you know, even with our team, fine tuning these models is non-trivial.”
Jesse Zhang Jul 30, 2026 ▶ 7:19 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Disclosure
Zhang: Decagon's token usage per conversation increases to improve quality
“And actually over time, the number of tokens we're using per conversation has gone up because we're actually doing more model calls to make the quality better, to do more checks, to parallelize more things.”
Jesse Zhang Jul 30, 2026 ▶ 13:49 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Disclosure
Zhang: Decagon fine-tunes models for use cases, not specific customers
“I think a common misconception that people have is, you know, fine tuning is, is a way to like customize it for that customer. In fact, most of the fine tuning we do is like customizing it for our use case, like the customer service use case.”
Jesse Zhang Jul 30, 2026 ▶ 16:42 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Insight
Zhang: Selling enterprise AI requires pitching vendor approach over category demand
“Generally in these conversations, we're not really having to convince people to like, Invest in this space. It's, like, more of, hey, we're the right approach for you, so you can partner with us.”
Jesse Zhang Jul 30, 2026 ▶ 40:52 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Disclosure
Zhang: Decagon seeded early sales team with Ivy League athletes
“The other profile we had a lot of in the early days were just like Ivy league athletes, I guess. And those profiles were kind of a good foundation for the group.”
Jesse Zhang Jul 30, 2026 ▶ 42:06 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Insight
Zhang: Enterprise AI Rollouts Should Be Piecemealed, Not Deployed All at Once
“One of the things that we really try to do is, you know, kind of take the project and piecemeal it. So we're not just deploying across every surface area, every use case at once.”
Jesse Zhang Jul 30, 2026 ▶ 45:47 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Insight
Zhang: Rigid 12-month product roadmaps do not work in AI
“Realistically in, in today's AI world, it's very difficult to have, like, a 12 month roadmap to a T. You maybe know how, like, some themes of what you want to build, but ideally, if you have those things, you should just build it, like, right now, because it's…”
Jesse Zhang Jul 30, 2026 ▶ 50:48 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Insight
Zhang: AI simplifies language localization, significantly accelerating software international expansion
“Language is a lot easier with AI. So in the past, maybe a blocker would be, oh, my language just doesn't work in, or my app just doesn't work in German or pick your language. But now it's a lot easier to adapt to your app. So I think for those reasons, interna…”
Jesse Zhang Jul 30, 2026 ▶ 1:01:31 How Decagon Runs 90% of Its Agents on Open-Source Models
a16z Insight
Zhang: Solo founders reach conclusions much slower without peers to bounce ideas
“I do think like one of the big struggles being a solo founder is you don't have anyone to bounce ideas off of. So you just arrive at conclusions a lot slower.”
Jesse Zhang Jul 30, 2026 ▶ 1:09:01 How Decagon Runs 90% of Its Agents on Open-Source Models
Zhang: STEM Competition Talent Holds Massive Untapped Potential for Startups
“Well, one of my big theses is that there's a lot of untapped potential there and to actually like turning them into people that, you know, want to do business or companies and things like that. A lot of them have historically gone into, you know, trading or ac…”
Jesse Zhang Oct 6, 2025 ▶ 5:30 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Founders should ask direct pricing and approval questions in discovery
“When you talk to potential customers, they actually don't mind answering questions such as, like, okay, if we built this for you, like, exactly how much would you pay for it? Like, would your boss need to approve it or your boss's boss? Like, who needs to appr…”
Jesse Zhang Oct 6, 2025 ▶ 10:58 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Defining good performance is hardest part of replacing enterprise human labor
“If you're going to be replacing human labor, you need to, you know, know what good human labor is. What we found is like, okay, well, can someone just tell us, like, what are all the, what are the answers to all these questions? And most people don't actually …”
Jesse Zhang Oct 6, 2025 ▶ 25:21 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: High hallucination rates prevent direct voice-to-voice enterprise deployment
“For enterprise use cases like us, like there's still a ton of hurdles to cross because those models, even though they're good, the hallucination rate's really high. So you can't really use them necessarily as is in, in kind of the current systems. And so a lot…”
Jesse Zhang Oct 6, 2025 ▶ 33:49 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Human-indistinguishable AI interactions require voice-to-voice architecture
“That is the biggest proponent of voice to voice, and ultimately the prevailing view is that first, whatever the final experience is, if you really want to make it indistinguishable from a human, you have to do a voice to voice or you have to at least take into…”
Jesse Zhang Oct 6, 2025 ▶ 35:10 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
INVEST LIKE THE BEST Assertion Not checkable as stated
Enterprise AI adoption is driven almost entirely by top-down board mandates
“Pretty much all AI initiatives are very top-down at this point, because it is such a board-level mandate, so the C-Suite's very, very invested in like, okay, where do we deploy AI? It almost means that if you want to get something going at a larger organizatio…”
Jesse Zhang Oct 6, 2025 ▶ 42:18 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Startups must communicate intensity upfront for candidate self-selection
“There's definitely a level of intensity that's important. And yeah, you definitely want to tell people that upfront because you want them to self-select into this culture.”
Jesse Zhang Oct 6, 2025 ▶ 57:08 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Winning top talent requires whole-team swarming like a sales process
“Like you, for anyone you want to hire, you need the whole team to swarm around them for, you know, to win. Highly sought after talent. And you have to go and, you know, do, do all the things, right? There are some parallels to sales, of course, like you, you'r…”
Jesse Zhang Oct 6, 2025 ▶ 59:26 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Application-layer AI talent competition is less extreme than at Meta or OpenAI
“Unfortunately in the application layer, it is not as crazy as, you know, the metas and the opening eyes who are just like, there's only so many top level researchers.”
Jesse Zhang Oct 6, 2025 ▶ 59:59 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Deploying smaller fine-tuned models in AI agents improves performance and latency
“You know how your agent is structured, you know the places where you need models to run, and you can take, you know, smaller fine-tuned models, and that improves the entire system, both in terms of performance, but also latency, and so on.”
Jesse Zhang Oct 6, 2025 ▶ 1:02:52 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Cognition and Cursor would anchor a five-company private AI portfolio
“I mentioned I'm close with the cognition guys, so cognition would be in there for sure. Cursor also I'm actually kind of interested in like where those might run into each other in the future.”
Jesse Zhang Oct 6, 2025 ▶ 1:05:14 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Enterprises must evaluate AI on holistic success rates, not zero mistakes
“There's the Waymo effect that often happens where It will be objectively just way better than human drivers, and human drivers make a lot of mistakes, but because we're investing in new technology, the bar is a lot higher, so it has to be near perfect. So ther…”
Jesse Zhang Oct 6, 2025 ▶ 1:07:01 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: Decagon maintains a strict principle against negative gross margins
“The only thing that we have a principle for is not to have negative margins.”
Jesse Zhang Oct 6, 2025 ▶ 1:11:26 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
Zhang: The layer directly solving the end-user problem captures the most margin
“That last step where you're actually solving someone's problem, that's where you generally can capture the most margin.”
Jesse Zhang Oct 6, 2025 ▶ 1:11:43 The Future of AI Agents | Jesse Zhang Interview · Invest Like The Best
20VC Insight
Zhang: Combining math Olympiad reasoning with sales skills is underrated
“If you can really unlock that level of, you know, reasoning capability and just like smartness and combine it with folks that can, you know, teach them how to sell or how to build a company, I think that's a pretty good combination. So that's something I think…”
Jesse Zhang Sep 19, 2025 ▶ 4:39 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
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