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Bret Taylor on AI and the Future of Software | Ep. 42

Bret Taylor is the founder and CEO of Sierra, an AI agent company transforming customer service. Bret’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI, co-creating both Google Maps and the Like button, and founding three companies. We unpacked the so-called “SaaS-pocalypse” and what AI agents mean for the future of enterprise software. We talked through the shift from systems of record to autonomous agents, outcome-based pricing, platform transitions, Codex and the transformation of software engineering, and who is structurally positioned to win in the next era of AI. Timestamps: (0:00) Intro (0:20) The SaaS-pocalypse and systems of record (12:34) Sierra's competitive landscape (17:05) Outcomes-based pricing (24:22) The rapid evolution of AI support technology (28:21) Young founders vs. experienced founders (34:12) Beyond support: The full customer lifecycle (38:47) Codex and the future of software engineering (51:49) OpenAI and advertising (54:59) How to run a board Links: https://x.com/btaylor https://x.com/jaltma https://uncappedpod.com/ Email: friends@uncappedpod.com

Bret TaylorguestJack Altmanhost
Feb 19, 20261h 0mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:000:20

    Intro

    1. BT

      Clearly, in three years, we could talk about what are the best practices to set up a software team that's optimized for this technology, and we'll know what those best practices are. And right now, we're just figuring them out in real time, and, like, my hypothesis is the companies that figure it out first will move the fastest. It's fascinating to me.

  2. 0:2012:34

    The SaaS-pocalypse and systems of record

    1. JA

      [upbeat music] Bret, thanks so much for doing this with me. I'm super excited for it.

    2. BT

      Thanks for having me.

    3. JA

      So you're one of the best people to ask this following question, which is: What is your view on the SaaS-pocalypse, if we can call it that?

    4. BT

      SaaSmageddon.

    5. JA

      SaaSmageddon. So basically, it's like-

    6. BT

      [chuckles]

    7. JA

      -you know, in public markets, all of these companies are trading way down. You know, you go on X, and everybody's talking about how, like, you know, software can now be written in two seconds, and so there's no moats anymore in software. And so it's leading a lot of people to ask, like, where does durability come from? And so I just wanted to sort of start with this topic because, you know, you've built your own companies, you've been the co-CEO at Salesforce, you're now building, like, one of the, you know, fastest-growing AI startups there is. You're on the board of OpenAI. How do you see software, like, in this moment in February '26?

    8. BT

      So first, I think the market isn't necessarily reflecting an indictment of individual companies. I think it's more of a, a broad view of, like, the, the bigger questions you were saying, i.e., every software stock is down, but I don't think that means every software company is equally disadvantaged. It's just basically anxiety about the future. I think it's a few things. Um, we can talk about sort of defensibility broadly. I think it's a really interesting question. I think if you look at the history of enterprise software, a lot of the value has gone to the big systems of record, so ERP systems, CRM systems, like the core databases that Oracle, you know, sort of famously powered in the early days of, of software. All-- and then you end up with all the software as a service companies, SAP, Workday, Salesforce, ServiceNow.

    9. JA

      Yep.

    10. BT

      If you look at what a system of record is, it's essentially a database with a bunch of workflows around it, and to date, those workflows are manipulated by people clicking on buttons in a web browser or filling out forms.

    11. JA

      If you had to, like, synthesize pre-AI, like, why were those businesses so good? Was it the source of truth thing, and that the-- there had to be some immutable thing, and so the database row, is that what it was? Was it the ecosystem of the integrations? Like, what, what do you attribute the success of systems of record to?

    12. BT

      So I think the reason why a system of record has always been the most valuable is it is the anchor tenant of your technology deployments. You know, if you wanted to, you know, create a workflow for a quote to cash or something like that, you had to integrate with your ERP system and your CRM system. So as a consequence, you know, the companies that sort of owned those databases could either develop that functionality as, uh, an add-on, like a, a new SKU, or if it was a third-party company, they would often be a part of the, the ecosystem, like Salesforce's AppExchange or whatever the marketplace equivalent is for SAP. And so you ended up with a lot of value in those systems, which meant switching costs were just really high because it was sort of this, uh, y- that system plus all the partners that integrated with it, sort of created gravity and, and high switching costs. And then similarly, you just end up accruing a lot of value, either by collecting rent from your ecosystem or developing premium add-ons on top. And so it sort of became the sun and the solar system, you know, for each of the different lines of business that these systems of record were sold into. And then you'd end up where you'd get a, a scale. So you'd get, um, sales capacity scale, you know, so the larger you grow, the more salespeople you have, you can reach more and more people. Then there's the proverb, "No one gets fired for buying IBM," which, uh-

    13. JA

      Yeah

    14. BT

      ... you know, obviously a somewhat dated-

    15. JA

      Yeah

    16. BT

      - you know, expression, but it sort of was like, "Hey, if you're gonna put in a new ERP systems, no one's gonna blame you for choosing SAP-

    17. JA

      Yep

    18. BT

      - because everyone chose SAP, right?"

    19. JA

      If you choose something new, and it doesn't work perfectly, big trouble.

    20. BT

      Then you're, you're this... Yeah.

    21. JA

      Yeah.

    22. BT

      So all those things sort of accrue. But then the question is now that all of a sudden that a lot of those start getting chipped away with AI agents. You know, first, could you just vibe code it in a weekend? So does it change build versus buy? So that's one risk. Does it change when you come up on that renewal?

    23. JA

      Mm-hmm.

    24. BT

      Are you gonna make a different decision? Secondly, I actually think the more fundamental thing is: What is the role of that system of record if AI agents are doing most of the work? So rather than people clicking around on an ERP system to onboard a vendor, if you just delegate to an AI agent to do it-

    25. JA

      Yeah

    26. BT

      ... all of that is sort of invisible to you, and all of a sudden, it goes from being an application to sort of a database.

    27. JA

      Right.

    28. BT

      Similarly, if you imagine a CRM system, and rather than having people staring at it all day to-

    29. JA

      Yeah

    30. BT

      ... manage their leads, contacts, and opportunities-

  3. 12:3417:05

    Sierra's competitive landscape

    1. BT

      any other time.

    2. JA

      I'd actually be curious on this topic of sort of, you know, there's these obvious things, and within AI, I would say, you know, no- not to discredit your insight, but support I would count as an obvious thing, like in a good way.

    3. BT

      Yeah.

    4. JA

      It looks like it works. And you did it, you know, early enough that you were able to get, you know, to a place, you know, at the right time, but other people did, too. And so in some ways, I'm like, you have been playing both in a very blue ocean, you know, wide fields, like, you know, the incumbents are sort of like categorically different. And so, like, it seems like inevitable that we're gonna have agents doing support, and so there's that. And then on the other side, you know, a lot of other companies see the same thing, a lot of other people have been building it. So before getting into the specifics, I'm just curious, like experientially, day-to-day, does, does your sort of operation of the company feel competitive or, like, wide open?

    5. BT

      It feels competitive, and it feels like a really big market. Um, so it doesn't feel particularly demand-constrained, which is a really great feeling. As a fellow entrepreneur, it's like you don't get to-

    6. JA

      So you feel like there's lots of demand, and there's like a contest with each sort of situation?

    7. BT

      Yeah, that's right. The way it feels, it feels like there's sort of too much capital available. Uh, put another way, there's obviously going to be competition in, in meaningful markets. It feels like there's sort of too many competitors that don't necessarily have strong differentiation. I think it's probably healthy, though. I think that, you know, uh, there will be a culling, you know, just a- as the market progresses. But it does feel, you know, quite competitive. I'll just sort of give you maybe, like, a quick glimpse of the past couple years. So we've had a remarkable growth rate at Sierra. We, we closed one hundred million in seven quarters, one hundred and fifty million in eight quarters, which has exceeded my expectations. But this past year has felt like an inflection point. So the first year of our company's history, we would often go in and be explaining to clients what an agent was. The term was, was novel, um, and it was part of our marketing-

    8. JA

      Mm-hmm

    9. BT

      ... explaining what an agent was. Number two, people would be talking about, "Hey, AI is maybe non-deterministic." They wouldn't necessarily use that word, but that would be what they would be describing. You know, "How can we trust this technology directly engaging with our customers or consumers? What are the risks?" Now, the conversation is: "Clearly, we need this yesterday."

    10. JA

      Mm-hmm.

    11. BT

      I mentioned this to you earlier, but over a quarter of our companies have ten billion or more in revenues. We're talking big companies. We serve most of the Fortune twenty, as an example. And so these are big companies that are coming in and saying: "We've evaluated it. We know what we want. Uh, we've heard of you. We've done all this evaluation. Here's an RFP. [chuckles] You know, like, let's go." And as a consequence, because the market has matured and, you know, uh, by the illustration of the existence of things like RFPs, you end up in more competitive conversations, and then it's a question of like: "Why Sierra?" You know, "Why Sierra?" And you know, I'm happy to talk more about that. I mean, I obviously love to, as I could tell you-

    12. JA

      Yeah

    13. BT

      ... all the reasons we're the greatest, but you end up in this world where you're not explaining what the word agent means anymore.

    14. JA

      Yeah.

    15. BT

      You're saying: "Here's why we're the right partner for you"-

    16. JA

      Yeah

    17. BT

      ... which is a very different conversation.

    18. JA

      Well, what-- I mean, so like, you know, they're like: "Yeah, I'm bought in on an agent." It's like: "Why is it Sierra?" Like, what have you found is like the most important thing that makes you win?

    19. BT

      So one thing we really did uniquely at Sierra, the reason why over a quarter of our customers have over ten billion in revenue, is we've tried to serve more complex, more regulated industries. You know, we want-- We serve most of the US healthcare insurance market, as an example. We serve US banks, Spanish banks, UK banks. Like, and these are companies that I, you know, as you-- if you know the industry, they're regulated by everybody. [chuckles]

    20. JA

      Yeah. Yeah.

    21. BT

      It's easy to make a demo in AI. It's why, like, you can go on X and just see a thousand demos, and, like, demos are cheap.

    22. JA

      Mm-hmm.

    23. BT

      But making an agent sort of industrial-grade is hard, and we've really uniquely been able to make agents that can actually have complex conversations. The other thing that we do really uniquely is, in addition to, I think, having a really easy-to-use product, is we help companies move faster. Um, uh, we went, uh, live with Cigna in, in two months-

    24. JA

      That's crazy

    25. BT

      ... which is remarkable.

    26. JA

      For Cigna?

    27. BT

      Yeah.

    28. JA

      I mean, how big is Cigna?

    29. BT

      It's a Fortune twenty, um, healthcare company, and I was on stage with Sachin, who's, who runs their AI practice there at the health conference, and he was talking about this. And part of that is like, how can you show up at a... Like, we're really great at AI. Cigna's really great at healthcare. How do you bring those two together to move extremely fast? And so for a lot of our clients, like, the reason they bring us on is they, "Can you help us move quick, move quickly?" And that requires knowledge of AI and knowledge of business, and I think we sort of show up with a, a greater sense of maturity there.

  4. 17:0524:22

    Outcomes-based pricing

    1. JA

      You mentioned like, um, you know, that the pricing scheme was one of the difficult things, you know, in the past era.

    2. BT

      Yeah.

    3. JA

      You know, we don't have to, like, belabor it, but obviously, you know, going from, you know, just buying a license to a cloud subscription, and now usage-based is, like, the future. Like, what are you feeling is important in, you know, as you have created and probably continue to iterate on pricing, like, what are the important levers for agent companies?

    4. BT

      We do something specific at Sierra that I'm sort of an evangelist for, which is outcomes-based pricing. So it turns out our industry, the outcome is usually well-defined. So in a service context, it's could the AI agent solve the problem? Uh, in a sales context, we do a lot of sales agents as well. Could it make the sale? You probably, uh, your company's paid your salespeople commissions, right?

    5. JA

      Yeah.

    6. BT

      Like, that's when you can measure the outcome, you want to incentivize the outcome. The interesting thing about agents is they're autonomous, um, or can be autonomous. And so if the outcome is measurable and trackable, what an interesting opportunity to actually charge for that. And if you look at the history of software, like, let's take advertising. We went from impression-based ads-

    7. JA

      Mm

    8. BT

      ... to cost-per-click ads, to now for mobile ads, you can do pay-per-install, as at least that's my understanding. And then you had, you know, enterprise software. You went from on-premises licenses to subscription-based software and, you know, could outcome-based software be the next? And what's so neat about that is, for a company-... What a interesting and accountable business model, and I think there's some challenges to it because, you know, you obviously put some revenue at risk, but I don't think most advertising tech people would say CPC ads put revenue at risk. It's like the opposite, right? Because the closer you get to the outcome, the more valuable it is for the companies. They're actually willing to, to invest in it. And so my view is, to the degree agents have a measurable outcome, outcome-based pricing feels like the secular business model for agents, and I think it's quite both disruptive and I think a huge step forward.

    9. JA

      Why is it better than token-based? So like, you know, if those are like, uh, you know, I guess sort of like the two reasonable options now, why is an outcome better than token-based, even over the long term?

    10. BT

      Let's say you had an AI agent to generate leads for your sales team. What do you care about? You care about the number and quality of the leads, right? And so you really don't care how many tokens the model uses. In fact, it's not obvious to me that, like, there's a correlation between used tokens and leads generated. Uh, and in fact, in, in, in the same way, there's no correlation in a SaaS product between the cost to serve and the quality of the product. You know, you can have a really good engineer write it or a really bad engineer write it-

    11. JA

      Right.

    12. BT

      -so it really comes to the quality of the product. The reason why I don't think token-based makes sense is it's charging for an input that is uncorrelated with the output that your clients actually care about. And I think this is actually, uh, you know, I'm a huge believer in applied AI, but I actually define applied AI as, can you describe your value proposition without, without mentioning models? Because if you think about, hey, we can answer the phone and solve eighty percent of phone calls without human intervention, with a CSAT score of four point eight out of five, that's-- you don't mention models. I mean, models are an input to that, but not output. If you have to mention token utilization, it's probably a tool. It's probably not an applied AI... It's not an application of AI, it's just sort of like a tool around AI. And I actually think that, uh, the closer you get to a business outcome, like it's actually, you should charge for the business outcome, which is uncorrelated with tokens. And I also think it's almost a measure of, are you actually an applied [chuckles] AI company?

    13. JA

      Yeah.

    14. BT

      If you can, if you don't have to talk about tokens.

    15. JA

      Do you think that there will be markets either where things get so competitive that people have to price based off of like, cost rather than value? Like, could that happen? Or maybe the other format for it would be if you can't describe the outcome cleanly. Like for example, code- coding, which we both probably think is super important, obviously, it's like a little harder to say what the outcome is there versus like usage or something like that. So like, what are the conditions where like tokens do make sense?

    16. BT

      Yeah. So I mean, there was this old Apple site where they had sort of like Apple folklore kind of thing, and I think there was this one boss at Apple that made people fill out a form saying, "How many lines of code did you write?" And this engineer infamously wrote a negative number because he had just like refactored a bunch of stuff. It's my-- it's like the good analog, historical analog for why tokens don't matter. Because it was, he was- it was his way of saying, you know, "Fuck the man," like-

    17. JA

      Mm-hmm.

    18. BT

      - "Your lines of code has nothing to do with my value." And he was doing it to sort of like, you know, piss off a middle manager to make that point. But what's interesting is like in the world of software engineering, people truly understand, like the customers of those right now are software engineers who intimately understand these models. So there's a little bit of a, the customer, uh, uh, product market fit. So it's a, it's a nuanced point, but I'll say like, where I see it might happen. So right now, if you're evaluating a software engineering agent, a coding agent, um, you're probably comparing it to the cost of a software engineer. Um, if you fast-forward five years, you probably will be comparing it to the cost of other coding agents. So I think the second-order effect as AI becomes prevalent is you, uh, you know, you're, you're just-- you're, you're the reference point for its value will change. The thing I would say is that's true where you're thinking about a cost center, but if you're thinking about top-line revenue growth, that doesn't necessarily apply.

    19. JA

      Yeah.

    20. BT

      And if you go to my example of an AI agent generating leads for your sales team, depending on what you're selling, a lead is a lead is a lead.

    21. JA

      Yeah.

    22. BT

      Um, and you probably will value quantity and quality of leads, and there's a math equation.

    23. JA

      Mm-hmm.

    24. BT

      And that probably will be remain independent of token costs-

    25. JA

      Yeah

    26. BT

      -is my guess. And so I think a large part of AI is productivity and, and reducing, you know, costs, and there's a big part of it, but the other side of it is outcomes. And so could you imagine a world in four or five years where, you know, there's one coding agent that can actually produce something of greater value for your company? Will you value that, or you just look at the token cost? I think probably you'll start looking for value, is my guess. Will they all be the same? I don't know. You know, it's like the-

    27. JA

      Yeah.

    28. BT

      Well, I was just reflecting on over the past year, there have been all these articles about has, like, AI progress slowed down? And then in our world of software engineering, it's been the opposite. Like, every new model comes out and you're like, "Oh my gosh, it can write increasingly complex software." My theory of that is, it depends on what you're testing. So if you're using ChatGPT for trip planning, you probably haven't seen a material change over the past year and a half because you reached sort of sufficient intelligence-

    29. JA

      Yeah

    30. BT

      ... for trip planning-

  5. 24:2228:21

    The rapid evolution of AI support technology

    1. BT

      time.

    2. JA

      Where are we at with support agents right now? Like, is, are there still edge cases, last mile things, like that AI can't do still?

    3. BT

      ... Yeah, we are, though I imagine a lot of the technical problems, uh, as opposed to product problems, will become easier, but there, there's a lot of them still. Um, so you know, we at Sierra support most spoken languages in the world, and, you know, if you want to support, um, Cantonese and Tagalog, most of the good voice models, you know, don't come from, like, the traditional Western model companies.

    4. JA

      Mm-hmm.

    5. BT

      Um, similarly, uh, one of our clients is Safelite AutoGlass, so it's like roadside assistance, and it turns out that, like, car horns, background noise, kids talking in the background, you know, are actually all fairly hard, uh, problems to solve. And even in some of the advanced voice mode stuff, if you are in a noisy environment, it, it, uh, constantly thinks it's being interrupted and things like that, so you end up having to build-

    6. JA

      Mm

    7. BT

      ... proprietary voice activity detection, multiple speaker detection, all these other things. We develop all this technology 'cause we need to be the best now, and I think we are the best now. And you're like, "Okay, that's probably gonna be a commodity two years from now, one year from now." I mean, who knows? But you have to do it 'cause you need to be the best at every stage of your company's existence. And I think then you're in a-- the way we think about the world is, we have a product, which is called Agent Studio or Agent OS, and we're to make the, the o- in three years, you'll judge us by our product, and right now we're probably... They don't, our clients don't really put it this way, but judge by the technology.

    8. JA

      Yeah.

    9. BT

      But if you go back to nineteen ninety-six, I remember when Netscape had a web server and Apache was new and da, da, da. Like, no one cares how you serve web pages now, like, it's a commodity.

    10. JA

      Yeah, yeah.

    11. BT

      But at the time, that was what you sold, and now you have increasingly higher order website building, like Shopify. So I just think the AI agent market's gonna take that progression. We're going from a tech-centric sales cycle to a product-centric sales cycle.

    12. JA

      It's interesting that you're obviously having to be the best at something that you know is gonna get commoditized.

    13. BT

      Yeah.

    14. JA

      Which is probably not something... I don't know if you've ever had to experience something like that in your... I mean, for that to be true, you just have to be in the middle of an insane rate of change. But that means you have teams who are putting, like, you know, a lot of their life force for two years into something that everybody knows is just for two years, but it still matters nonetheless.

    15. BT

      It's crazy. I mean, if you look at traditional, I'll just say enterprise software, consumer's a little different, but you think about you're building up this asset, your intellectual property. There's a fancy name for it.

    16. JA

      Nice word.

    17. BT

      It's like, look at this platform that we're building, and, like, we took so many years to build it, and it's got all these features, and now you're like: I'm building this, and I'm a hundred percent certain we'll throw it away in the next fourteen months.

    18. JA

      It's a sandcastle, yeah.

    19. BT

      But I have to build it, because if I don't, I can't serve the bank that has a big, you know, business in Hong Kong or whatever it might be, where they-- we need Cantonese support. So th- that is the reality right now, and so I actually think... I've been thinking a lot about this, actually, just because, uh, I think it was Toby Lucow sort of said something provocative around, you know, when generating the code is, is easy, it's almost like the, the system and the prompts that are actually the durable asset. Uh, you know, put another way, could you sort of terraform your software from scratch? You know, it's the prompts that led to it. I do think that is sort of the software of the future in a lot of ways, where how do you encode the infinite number of little product decisions that you made? Um, because so much of that is encoded in, in code today. Um, I mean, if you think about, like, a product requirements document versus the code, what percentage of the, uh, emergent product that comes out of it is in code? Almost, like, ninety percent. Like, a lot of the little detail-

    20. JA

      Yeah

    21. BT

      ... are in there. I think a little bit it's like software companies of the future and the products that they make are just gonna take a really different shape, uh, in the future, and I, I'm so excited to be a part of it. I, I mean, I think it's really fascinating. I think there's something really interesting about AI impacting the software engineering industry almost first and most.

    22. JA

      Yeah.

    23. BT

      Uh, because, like, we're disrupting the craft of making what we're building in real time, and it's fascinating.

    24. JA

      Yeah.

    25. BT

      It's a fascinating time.

  6. 28:2134:12

    Young founders vs. experienced founders

    1. JA

      I think there's a prevailing idea in tech that AI is moving so fast that, like, young founders have this massive advantage, and I mean this with no offense. You're not old, but you're also, you're not the youngest-

    2. BT

      You're saying I'm old. I got it.

    3. JA

      No, no!

    4. BT

      Yeah, yeah, yeah.

    5. JA

      But you're the youngest founder-

    6. BT

      Yeah

    7. JA

      ... and you have one of the most successful AI startups there is. And it does seem like you've brought a lot of your previous experiences to what you're doing, but I can tell from talking to you that you also are just rethinking everything. And so I'm curious your own experience for yourself and for other founders you look around at, like, do you think, by and large, young founders have the advantage? What does it take for more experienced founders to have the advantage?

    8. BT

      You know, I'm always a big believer... There was, I don't know if it's a real quote, but I- some VC said, you know, like, uh, "Why was this, you know, founder able to, you know, conquer this market where so many others had failed?" And they said, "Well, he was too naive to know it couldn't be done." And there's a certain element of that that I, I love because you end up with this kind of naiveté that is actually sort of a form of principled, first principles thinking that a lot of young founders have. You know, you just don't know why this messy, bad product, you know, dominates the market. You think there's a better, faster, cheaper way to do it, and because you, you don't have any of the hard-won lessons that can end up, uh, you know, oversimplified analogies g- keeping you from actually taking that leap, you can end up with, you know, Tony made DoorDash and didn't care about, you know, say, Webvan, Monzo, or whatever it was called.

    9. JA

      Yeah, yeah.

    10. BT

      I can't remember all the, the, the dot-com, uh, bubble companies. But I do think, especially in enterprise software, uh, the experience that, that, uh, some of our team members bring, including the old man, me and Clay, bring to it, really does matter. You know, part of the reason we're able to serve, you know, so much of the Fortune one hundred is we can go into a bank or a healthcare payer, a healthcare provider, a revenue cycle management firm, or a big telecommunications company and understand their business. Under-- we're working with one large medical device company that's consolidating forty of their call centers into one, and we can have a discussion about, like, the change management of doing that. And that's not really a tech problem, but it does require, you know, understanding business, and I think there's like- we always joke at Sierra, it's like the, the Venn diagram, like, there's a circle of people understand, like, next generation of AI-

    11. JA

      Mm-hmm

    12. BT

      ... and the people who understand business, and we're, like, the company right in the middle of that, and maybe the only one.

    13. JA

      Yeah.

    14. BT

      And that matters because, I don't know, there was that sort of infamous MIT study saying all these AI projects fail. It's like, none of ours do, and that's our value proposition. Like, we can actually help you go live, and I think the experience has benefited us.

    15. JA

      Yeah. I'm curious, like, if you can point to what has created the lead you have so far, and obviously, I know you're just getting started, but at the moment, you do, you know, you've, you've, you've pulled away in a big way, and, um, I'm sure there's a lot of just, like, daily blocking and tackling, but I'm curious if there are any, like, foundational decisions that you've made or strategic approaches that, you know, over the last couple years, you look back at and you're like, "That was pretty essential to make this happen?"

    16. BT

      ... I think there's two almost independent, um, areas of investment. Not, not-- They're not independent, but they're like, uh, very different. One is the product, and one is our sort of our go-to-market and partnership model, and they're both really intentionally built. On the product side, we've tried to balance ease of use and of extensibility because when you serve really large companies with very comp-- that have been around for two hundred years, you know, you need to work with mainframes, you need to work with a thousand different systems. You've done ten acquisitions. There's all the, like, enterprises are messy. And so that's why you tend to have, you know, most, uh, I'll say, enterprise software that's designed for larger companies tends to be quite extensible. Often, that extensibility comes at a cost, which is: Is it easy to get up and running? And so, as a product designer, like, one of the things I've just spent a lot of time thinking about is, like, we're trying to have our cake and eat it, too. Like, can you go live in two months and still be maximally extensible? And I'm really proud of the product we've built, and some of that is born from experience of what does extensibility mean. And I think we have an opinionated view of what it means and have been able to accommodate, like, some fairly exotic deployment requests and still do it fast. That's really unique. The second thing is our go-to-market and partnership model, becau- we knew when we started the company we wanted to work with the largest companies in the world. Not only, but we wanted to be able to work with the largest companies in the world and have focused on that, and as a consequence, we just have a really unique partnership model. Um, there's sort of a fashionable thing to talk about, forward-deployed engineering in Silicon Valley. We don't call it that, and it's a very unique model 'cause it's not all about technology. Like, most of our clients build and maintain their agents themselves. It's pretty easy to do, but we show up, and we help you be successful. And so it's like, we'll just show up. Like, we're not gonna let you fail. Like, and I think that is a very different... Because we have this outcomes model, outcomes-based pricing model, we don't get paid unless it works.

    17. JA

      Yeah.

    18. BT

      And so-

    19. JA

      How much of that is technical versus, like, change management?

    20. BT

      It's a mix of both. Uh, you know, I don't know if it's fifty-fifty, but-

    21. JA

      Do you do it as two people, or it's one person who does both?

    22. BT

      We have a mix of roles. Uh, we've sort of evolved that. Uh, we try to hire really technical people in all roles, though, because part of our, our secret is we want, we wanna be, like, be your trusted partner in AI. So you want the person who is working with you every day to be the most knowledgeable AI person you know. [chuckles]

    23. JA

      It's like a, like a forward deployed change management engineer.

    24. BT

      Yeah. Yeah, exactly. [chuckles]

    25. JA

      It's crazy what we're doing.

    26. BT

      And so, and what's really neat about it is, if you're, like, a really talented technical person who wants to go transform an industry, you can do it at Sierra. I mean, you can go in, and, like, we're working with most of the healthcare insurance companies. Like, you wanna change-

    27. JA

      Yeah

    28. BT

      ... healthcare costs? And, you know, like, what a cool vantage point to do it. So we've been able to attract some really remarkable

  7. 34:1238:47

    Beyond support: The full customer lifecycle

    1. BT

      people, too.

    2. JA

      You said that it's not just support agents now.

    3. BT

      Yeah.

    4. JA

      So, like, what else are you finding shoots in?

    5. BT

      I'll give you one of my favorite relationships with Rocket. So based in Detroit, remarkable story. Uh, you know, their founder's done more for Detroit than I think any one person's done for any city, just like, remarkable company. But they own Redfin, which is a home search site, Rocket Mortgage, which, uh, is, like, the number one consumer mortgage originator in the country, and then they, uh, bought a mortgage servicing firm recently as well. And you can go to redfin.com and use an AI agent to search for a house. You can go to rocket.com and finance that house with an AI agent, and then you can, with the acquisition they did of this mortgage servicing firm, you can then, when you're servicing your mortgage, you'll talk on the phone with a, an AI agent as well. So, like, everything from finding a house-

    6. JA

      Yeah

    7. BT

      ... to originating the mortgage to servicing that mortgage, I think is pretty cool.

    8. JA

      Yeah.

    9. BT

      And, like, they have an amazing CTO named Shan Malhotra, like, pretty visionary, uh, and I love their CEO, Varun, too, but it's like everything from finding a house all the way through servicing. It's kind of what we believe a lot of businesses will do, is like, look at their entire customer lifecycle from, uh, you know, I'll say purchase consideration, which is a fancy way of saying, like, browsing. I think homes are probably one of the more considered purchases that you could do. They're executing the purchase, they're having issues with it, all the way through, you know, retention. And for a lot of-- for example, a lot of our telecommunications customers, their AI agent is actually doing negotiations.

    10. JA

      Mm.

    11. BT

      So, like, you've probably negotiated your cable bill at some point.

    12. JA

      Probably.

    13. BT

      You know, probably. And so our AI agents are doing billions of dollars of negotiations for everything from, you know, uh, ca-- satellite radio subscriptions to cable television subscriptions.

    14. JA

      Yeah.

    15. BT

      It's pretty cool. I mean, it's, like, really, uh, you know, over a billion dollars in mortgage folders a month.

    16. JA

      Basically, just, like, all transactional communications eventually.

    17. BT

      The way I think about it is, website is a technology, but your dot-com, the one with your brand at the top, is your website.

    18. JA

      Mm-hmm.

    19. BT

      We're sort of doing that for agents. It's sort of like agents will do a lot of things. The one with your brand at the top that your customers go to, whether it's buying or servicing, we would like to help you make that. And I think it's, it's an interesting, a- as agents go, um, it's pro- often interacting with other agents, right? If you think about a, a home and auto insurance company, you know, you may have a, a claim adjudication agent, you know, that's quite complicated. So our agent that's having the phone conversation when you're in the fender bender-

    20. JA

      Yeah

    21. BT

      ... will interact with that. But it is almost the intersection of all of the, that technology because it's sort of your, your front door. And our whole hypothesis is, every company needed a website in 1997-

    22. JA

      Yeah

    23. BT

      ... every company needs a, an agent in 2027, and, like, we wanna be that, that company.

    24. JA

      What's the nuance about, like, agent builders, though? 'Cause I know you have, like, a view that, like, just being, like a generic agent builder is not the right thing.

    25. BT

      Yeah, I mean, I've been surprised how many enterprise-- like, large incumbent enterprise software companies, like, their first foray into AI was you can... an agent-building tool.... It just feels inevitably to be a commodity in my mind, because, uh, you know, maybe making a website was hard in nineteen ninety-five, but today there's like a million ways to make a website, and most of them are open source. So you have like cool companies like Vercel, which I love, but it's not like there's a huge market for this stuff. Um, and, and in practice, I think the same will happen with agent building. Um, I think OpenAI will have a great tool, probably all the foundation model companies will. There will be open source packages like LangChain and LangGraph.

    26. JA

      Mm-hmm.

    27. BT

      The idea that you, you have the right to win there, I don't know if anyone has the right to win there, just because it's just a technology. It's a horizontal technology, and I just believe in open source, and it's just gonna, um, become a commodity. So my belief if-- where there's value is really going to be in agents that do things, and you'll, uh, hire those agents and purchase those agents for what they do. So I believe in companies like Sierra, I believe in companies like Harvey. I really admire what they do, and, you know, they have an agent that will do an antitrust review. Uh, you know, I think there'll be a finance agent that audits your financials. There will be one that helps you onboard a, you know, supply chain vendor. There'll be one that, uh, you know-- If you just think about onboarding a new vendor, it's like there's a procurement process-

    28. JA

      Yeah.

    29. BT

      ... there's a legal process, there's a contract review process. Whether or not it's completely autonomous or human-in-the-loop, all of that could be augmented with an AI, and I'm like, "That's a product."

    30. JA

      Yeah.

  8. 38:4751:49

    Codex and the future of software engineering

    1. JA

      Yep. Speaking of the platforms, um, aside from being the founder of Sierra, you're also on the board of OpenAI. You're the chairman there. I wanted to ask you specifically about Codex. Like, over the last, you know, couple weeks, it's been unbelievable. It's like, you know, a curtain just came down. Did you expect this? Like, did you think that what has happened here was gonna happen, or like, when did you start to have an inkling that, like, code was gonna go vertical like this?

    2. BT

      I'll say yes, I expected it just because, you know, being on the board of OpenAI, we talk a lot about it and all the labs, uh, uh, Anthropic and OpenAI in particular, talk a lot about using coding agents to help build AI. And, and certainly, like, building an AI researcher is an important part of building an AGI lab. The weird part about it for me, as someone who is a software engineer, um, I didn't feel it until I used it. So you-- like, you can talk about it all the time, and then, like, the first time you one-shot something and it turns out, like, really good, and not like slop, but, like, really good, it's an emotional experience, I think. I mean, for me, it was. It was just sort of like, "Holy shit!" Like, "This is real."

    3. JA

      Yeah.

    4. BT

      As you said, it's really over the past three months that it has felt really materially different to me, and I've been thinking about it a lot. Um, I was thinking about the past twenty years of software engineering. Um, I remember the first time I w-- uh, worked on an engineering team that had real CICD, where you'd check in code, and it would just automatically end up into production. And I remember how-

    5. JA

      Mm.

    6. BT

      I'll, I'll just like-- I- if you've ever worked in an engineering team that did that versus one that did manual releases, it's completely different. Because to have something that can safely go from commit to production, there's so many things that have to happen to make that work. You end up relying a lot on testing, so both unit testing, integration testing, and canary testing, because the last thing you want is someone clicking a button and taking down the service. And it's almost impossible for a team that is doing manual releases to convert into CI, like true continuous delivery, because there's so many implied processes that are incompatible with that. It's, like, easy to start that way and, and very hard to work. So I've been asking myself, clearly, in three years, we're gonna-- like, if we were talking, we could talk about what are the best practices to set up a software team that's optimized for this technology, and we'll know what those best practices are. And right now, we're just figuring them out in real time. And, like, my hypothesis is the companies that figure it out first will move the fastest.

    7. JA

      Yeah.

    8. BT

      And, and the [chuckles] other part of that is the companies that don't will move much more slowly. It's fascinating to me. Uh, and Andrey Karpathy, he had a really interesting post about this, too. Like, I think a lot of folks who are sort of, like, in deep here have been thinking about it, and it's fun to see the industry you love sort of flipped on its head and- [chuckles]

    9. JA

      Yeah

    10. BT

      ... in real time.

    11. JA

      Well, it's interesting because, like, I think people, like, you know, software engineers on one end, and then, like, say, somebody who's like, you know, in, you know, some part of the country where AI has not yet kind of like gotten its tentacles-

    12. BT

      Yeah

    13. JA

      ... fully extended. Like, there's, like, a wide gap in people's current sort of comprehension of, like, what AI's gonna do. And so I think, you know, it's like, it's a little bit unknown. Like, you know, there's a lot of blog posts going on right now that are breathlessly saying, like, "It's all over." I think, you know, I'm probably more in the camp of, like, maybe software is like, I don't know, sol-- people, you know, use the word software as solved. I don't know if it's that, but I'm curious if you have a view on, like, if Codex and Club Code and sort of like the, the latest in coding, is that going to change the way companies are built? You know, like, one easy straw man question there would be like, you know, people have been claiming that there's gonna be my brother, you know, these ten, ten-person billion-dollar companies. You know, is that-- Are we at the precipice of that? Does that make sense? Are there other changes? Like, what's gonna happen now?

    14. BT

      There probably will be a ten-person billion-dollar company, but I don't necessarily think it'll be the norm. Uh, and the reason for that is competition. If you imagine, like, the mobile phone market in the United States, there's three main competitors: Verizon, AT&T, T-Mobile, and they're all competing for a fixed pie of mobile subscribers, and it's why it's extremely competitive. There's promotions, there's ads.

    15. JA

      They can't make more of us.

    16. BT

      They can't make more of us. They can build up their network, they can do other pricing, packaging, uh, and, and it's a really complex business to run.... all of them have access to AI, every single one. So the idea that you could deploy AI and, you know, not have to do things that you are doing currently because of AI is probably true. But if any one of them figures out a way to use a person to gain market share against the other one-

    17. JA

      Yeah.

    18. BT

      -they're going to do it.

    19. JA

      Yeah.

    20. BT

      And then as a response, their competitors will do it, too. And that's how, you know, we spoke about this earlier, but it's the reason why when automated teller machines were introduced to banks, the teller job went away. But there's no fewer bank branches and no fewer people in those bank branches, and it's because, I don't know if it was JPMC or someone figured out, "Hey, if we put financial advisors in there-

    21. JA

      Yeah.

    22. BT

      -and other things-

    23. JA

      Right

    24. BT

      -we can actually make more revenue per branch."

    25. JA

      Yeah.

    26. BT

      My personal take is in a competitive market, and that's the key, by the way-

    27. JA

      Yeah

    28. BT

      ... you need competition, so people can't just pass the cost savings on to shareholders or dividends. The second-order effect of the efficiencies of AI will be investment-

    29. JA

      Yes

    30. BT

      ... to compete: lower prices or customer acquisition, or whatever it might be.

  9. 51:4954:59

    OpenAI and advertising

    1. JA

      Yeah, makes sense. My last question about AI, there was a shot from Anthropic at OpenAI around the Super Bowl commercial about the ads, which was-- they were good ads. They were funny. Um, but then it, I think, sparked, like, a debate around sort of like, the whole topic of like, what is the role of these foundation labs, and, um, how should they sort of like, bring AI to the masses or not? What's the appropriate business model? What are the trade-offs of all of this? You've obviously, like, you know, you have experience with social networks and a lot of different pricing, you know, models. You know OpenAI well. You know, you know how to consume AI. So I'm just curious how you think about this, and like, what is the right thing when you consider, like, a lot of these dimensions?

    2. BT

      I'm very optimistic about ads done in sort of a tasteful way. Um, you know, I started my career at Google. I think I arrived, like, the day AdWords came out, so... A- and it was just interesting because when I started there, you'll laugh at this, but like, everyone in my family, when they found out I was working there, was like: "How do they even make money?"

    3. JA

      Hmm.

    4. BT

      I laughed just because I was-- I think I listened to the Acquired podcast. It's literally the most profitable business ever created. [chuckles]

    5. JA

      Yeah.

    6. BT

      But as a consequence, you know, Google is widely available for free for people who want to use it and has created an economy around it for demand fulfillment advertising. I think there's reasonable criticisms of advertising, you know, if it starts to get in the way of the sanctity of what the AI is recommending to you, which was sort of the, um, you know, backhanded implication, but I just think it's not true.

    7. JA

      Totally.

    8. BT

      And so I actually think if ads are clearly labeled and, you know, not-

    9. JA

      Yeah

    10. BT

      ... tainted in the experience, I think it's really aligned with the, the OpenAI mission because our mission is to ensure artificial general intelligence benefits humanity. Obviously, the most important part of that mission is safety, but after you get back the Hippocratic oath, "First, do no harm-

    11. JA

      Yeah.

    12. BT

      ... the job of a doctor is to cure you."

    13. JA

      Yeah.

    14. BT

      So then after you say, "Okay, it's safe, how do we widely distribute it?" And I think we have an obligation, being a mission-driven-- You know, I'm, I'm the chair of the foundation and on the PBC board.

    15. JA

      Yeah.

    16. BT

      Like, our mission matters, and being able to offer it for free widely is a huge part of that, and we need to be able to, to-

    17. JA

      Yeah

    18. BT

      ... afford that.

    19. JA

      Yeah.

    20. BT

      I think it's not only... I just, I find it inauthentic. Like, I'm like-

    21. JA

      Totally

    22. BT

      ... this is an incredible opportunity to provide this at scale-

    23. JA

      Yeah

    24. BT

      ... to society, and I think the idea that it, it will somehow taint the experience is, is wrong.

    25. JA

      It's funny. You know, like, I grew up in, like, a suburb of St. Louis, and, you know, so it's, like, a whole different world than, like, you know, what we're in now, and it's like when I think about, like, you know, people, you know, that I grew up with or, you know, from just other parts of the country, twenty bucks a month is a lot. And I think, you know, it's easy to forget in our ecosystem that, like, not everybody wants or can spend twenty dollars a month on stuff, but they really want these services. Like, you know, if the whole world had to pay for Google, like, that'd be a worse world.

    26. BT

      Absolutely.

    27. JA

      Like, it's really good that everybody has access.

    28. BT

      I just think it's important we do it well, and-

    29. JA

      Yeah. Yeah, no-

    30. BT

      And we will, you know.

  10. 54:591:00:37

    How to run a board

    1. JA

      yeah. Yeah. The last thing I wanted to ask you about was, um, how you've chosen to sort of, like, finance the company, and I guess I'm curious about three parts, which are how you got started and, you know, working with Peter Fenton, and then, like, what you've done since then to date and what's been important for you. And then I'm curious, just like, as you think about the future, like, what's important to you as you think about other partners or capitalizing and, you know-- Mm, I'm asking just 'cause this is a podcast that has a lot of VC in it, so I've gotta have a little flourish.

    2. BT

      Yeah, totally. Um, we have, uh, three members of our board, which sort of represent kinda like our kind of, uh, three rounds of investment. So Peter Fenton from Benchmark, Ravi Gupta, who, uh, just, uh, left Sequoia.

    3. JA

      Yeah.

    4. BT

      He's still a venture partner there.

    5. JA

      Yeah.

    6. BT

      And Neil Mehta from Greenoaks. Um-

    7. JA

      All good.

    8. BT

      Just a fantastic group of people and chose them all, both for the firm and the person. Um, but notably, like Peter, uh, I've worked with in both my previous companies, so, uh, you know, our first round of financing, I didn't talk to anyone else and, uh, introduced him to Clay, my co-founder, who hadn't spent time with him, and, uh, we ha- talked once. He sent me a term sheet. I signed it, no edits, and it was, like, a very much a, uh, trust relationship. And, um, it is interesting, like, one of the things I really have appreciated about... So there's some downsides to Silicon Valley and our, our, you know, how insular the community is. One of the great parts, though, is just, like, the relationships you can forge over years, and for me, it meant-... Peter and I could sort of start on third base just because we've worked together a lot before, and so you just don't end up with a lot of the- there's no, no funny business in the fundraising process, no funny business in the boardroom. It's just like, "Let's get to work," and, uh, it's fun. It was fun to, you know, sort of get the band back together there. But the fun part for me is I had never worked with Ravi or, nor Neil before-

    9. JA

      Yeah.

    10. BT

      - and, and, like, Clay and I are just-- it's like, it's just a, it's just a great board.

    11. JA

      Yeah.

    12. BT

      Um, like, it's just like people we seek out advice from, as opposed to people we report to, you know, every quarter. It's, so it's amazing.

    13. JA

      How do you think about-- 'cause you're both, like, known, like, you know, when, when OpenAI... We, we won't go back through the story, but, like, you know, when OpenAI had its, like, oh my god moment, like, Sam was like: "You, Bret, you gotta c-," like, you're, like, the board member, and then you've also got a board that you're-- so you're, you're in both roles at once. How do you, like, make the most out of a board? Like, you know, obviously, you've got these particular relationships, but, like, what do you expect that relationship to look like?

    14. BT

      First, I really like written documents for boards over presentations, both as a board member and as, uh, like a, a f- founder of a company, because you end up letting people synthesize information ahead of the board meeting, so you end up with more substantive discussions in the boardroom. I've done this for the last, uh, two companies I've started, and it's just been great to send out a, you know, a board document. Sometimes people will comment ahead of the meeting, but I actually think the main thing is it, it's been read-

    15. JA

      Mm-hmm.

    16. BT

      - and it's been read ahead of time. And then you end up with a meeting about the actual meat and potatoes of the topics. You're not, like, staring at a bunch of sales numbers for the first time.

    17. JA

      You're not running through slides.

    18. BT

      You're not running through slides, and I find it to be incredibly im- I, I think most companies should be run, um, this way. The other thing that's really interesting is, like, don't write it with AI. Uh, it's so funny to have to say that now, but I find that-

    19. JA

      The process of the writing?

    20. BT

      The process of the writing is a process of clarifying your thoughts.

    21. JA

      Mm.

    22. BT

      And so for Clay and me, this is a process by which we synthesize-

    23. JA

      Yeah

    24. BT

      ... what's been happening, and you know it, you talk about it, but to actually write it and write it eloquently and concisely is incredibly important because it's essentially a way of... You know, it's like, what's that famous line?

    25. JA

      Mm.

    26. BT

      "If I had more time, I would've written a shorter letter." Like, spend the time, 'cause that's actually how you can show respect to your stakeholders, that you're thinking about the strategic issues going on in your business. And the last thing I'd say is, um, board members aren't sort of single-issue voters, but they- everyone has their strengths. And, you know, at, at OpenAI, we've recruited a pretty diverse set of skills. Zekea Coulter is a professor at CMU. He's a, uh, specializes in, among other things, jailbreaking, so just, like, one of the experts on some of the more subtle safety aspects. Uh, and Nicole Seligman was v- you know, a great attorney, and, you know, she's an expert in a lot of, like, legal issues. And what's really nice is when you grow out a board, you know, beyond sort of your initial investors, too, is find people that your management team will want to go to for advice. Obviously, the audit committee chair and your CFO have a really unique relationship, um, but you really want folks like, who's your head of sales gonna go talk to? Do you have someone who's, like, kinda been there or done that? Because you want them to have that kind of like... I always think of it as like, who are the advisors you want to surround your management team with? And I think a functional board really has those relationships, and then when you're in a board discussion, you have all these board members who have had lots of engagement with the company, but in a really valuable, kind of targeted way. So I like to think of the board as a collection of people.

    27. JA

      Yeah.

    28. BT

      Don't look at the individuals. It's a, it's a- the whole should be greater than the sum of its parts.

    29. JA

      Anything this year you're particularly excited about that you can share?

    30. BT

      I think the real exciting part is going to be adoption in regulated industries. Uh, I think we, we're moving beyond, like, the early adopters-

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