YouSaid · the spoken record

Clay Bavor

lines on the record: 66
first: 2026-07-04
most recent: 2026-07-04
sittings or episodes: 1
sources: podcast

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“Get breakfast. She would make up a doctor's appointment or something for me, and then we'd go to Macworld, and I would get to spend the day at Macworld, which for me was like Nirvana. And so I feel such gratitude to them and seeing in me that interest and how I lit up about this thing that was unfamiliar to them, but that they then pushed and enabled. And of course, there's a direct line from that to wonderful 18 years at Google starting Sierra and today.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I feel such gratitude to my parents. I'm sorry if it's a straight down the fairway answer. My father was a career cardiologist. My mom is a very talented quilt maker. Neither of them were an engineering or technology. And they saw that when I got a hold of my first computer, I just lit up, not really understanding what computers were about. My mom was good with them in the 80s, but it was not at all clear where they would go, but they could see that I was obsessed with them. They supported that interest to the hilt. I remember going with my father and my mom and dad to buy an early power Mac. And, you know, my dad was pushing like, would you be able to do more if we had more memory in it? I think I would be. And it's like, well, we should get more. It's like, is this real life? My mom would take me out of school one day a year and we would go to Ken's house of pancakes.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Mention married to my high school sweetheart, we will have been together for almost 30 years. And I'm not that old. I think a great marriage is a partnership. And a partnership means you are working in pursuit of in service of some shared set of goals. And so you asked about interest. I think having shared interests in what you were pursuing as a partnership is deeply important. Happy kids who grow into adults who can enjoy their lives and contribute meaningfully to those around them building a set of values in one's family that are aligned with your own. And then I think ensuring as part of that partnership that the other member in it themselves thrives and fully realizes themselves. And there are those interests may be different, but there can be a shared interest in enabling each other.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“And then the other is making kids' interests your own. And so I'm terrible at basketball. My eldest son is an incredible basketball player. I am so proud of him. I go and watch him play and say, he does things. I could never do that, not only can't I do that, I could never do that. And so I follow the playoffs. I've learned about the sport. I've learned about the best players. I've learned about coaching so that I can try to enjoy and support him in this interest more fully than I otherwise would be. And so I think for each of our four, it's being aware of what gets the synapses going for them, what they light up about, and then making that interest my own.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I look okay. Sounds good. Fantastic. It's amazing. Well, thanks for the 1940s, 50s. That's great. I'm looking forward to that one First of all, having kids is the greatest gift. It is such a privilege. And a few things I would say, first of all, you will be a changed and different person. On the other side of holding your son or daughter, it's just, it is the, in my opinion, single fastest rate of change, single biggest change that anyone experiences in their life after they themselves are being born, right? Welcoming your first child. I try to carve out time, family dinner. We have many mornings on Sundays, maker mornings with two of my sons where we block out an hour or two and we build something at home. And so rituals and discipline around making time and space, anything important in life, my view is a product of clear goals and good habits. And so I think if you have a clear goal around how you want to be as a parent and then habits that help you build towards that, I think that's a very important ingredient.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“David McCullough, the Wright brothers. It's so good. It's so good. It's a tight history of obviously the invention of the first heavier than air aircraft. And to me, it is as accurate a portrait of entrepreneurship and invention as has been written anywhere. The aircraft could not have existed without this kind of network of pre-existing inventions, most importantly, a lightweight internal combustion engine. And then it was try. It didn't work. Try, it didn't work. There's scenes of them stuck out in North Carolina being eaten alive by mosquitoes. It's the hardship and then the triumph of having built something that flies.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“What people underestimate about Google is when you have the alignment of an ambitious, enduring mission, incredibly smart people and a culture that values truth and building in service of that mission. That company can kind of solve anything. People sometimes criticize Google for a thousand flowers bloom. If you have smart, well-meaning people caring for every one of those flower beds and they're directed in the right way, it is quite a force for invention and discovery and building new things.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Such a gift. Cinder has a remarkable ability to look at a problem from wildly different Zoom levels. His dynamic range and thinking is second to none, zoomed all the way out highest level strategy. How is this going to unfold over the next five years? All the way into the details, the pixels, the drop shadows, the sound, the texture of something. And I have tried to emulate that, talk about surrounding yourself by great people or having the privilege of working for someone. I observed a leader who is extraordinarily focused on the product, the work, building something great also is just a wonderful human being and deeply focused on the humanity and folks around him.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“But honest respect when it comes to instincts on how to sell, it was like, yep, okay, makes sense. Brett's instinct on system design and architecture are second to none. And so I trust his judgment more than I trust my own. On people stuff, on kind of the building and running of the company, it was like whatever Clay size. I would go with that. So that's probably the rough yin-yang major minor split.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“We think about rather than dividing up the company, we think about majors and minors for every part of the company. So Brett's majors are definitely sales and then engineering. He is really good at selling software. He is really good as a software engineer. Still, I major in what I've called like the running of the company. So operations, finance, legal, and so on. I do a lot of first calls. He understands our most important contracts for things that are highly consequential on how we run the company. We have kind of two nuclear keys that we turn on those. Brett, having spent time at Salesforce, really learned from the best. Like Mark is extraordinary.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Couple weeks ago, we were trying to figure out how to get something to move much faster in one space. It's interesting. We basically always converge. It's like we're highly truth-seeking. It's like, what is, we have a funny expression. It's like, this is correct. Okay, what does that mean from some objective, truth-seeking perspective, like this is the right way to do it? So we try to get to, okay, what is the correct solution? I was on one side, it was like, I think we need better kind of process and structure around this thing. Brett was on the side of people. Maybe we need different leaders or different leader in this space. The answer is with most things, like turned out to be some of both, right? Turned out to be some of both. We started from, no, it can't just be solvable. It's like, no, it's not just people. And, you know, we pull on those threads. And this wasn't think apart, think together so much as just kind of interrogating each other. Again, with the goal of just getting to the”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“In terms of importance, it is obvious to me that it has never been more important given that the kind of offensive capabilities just ratcheted up five notches. I think cybersecurity seems like a pretty good bet to me. The question is whether the offensive tools turn to be defensive tools if actually mythos and codex 55 cyber, if they themselves are the solution, not more narrowly focused cybersecurity product.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, we completely changed our engineering interview process. So it now looks much more like here's a kind of prompt. Think through an application you would like to build. Cool. Okay. Here's $150 to spend on choose your coding agent. You can use whatever setup you want. Use whatever tools you want. Bring your own laptop, bring your own tools. We're going to pay for your tokens. And then build it. Tell us how you went through building it and so on. So at least in engineering, it is an AI native interview. And of course, we test for architecture, systems design, product thinking, culture, smart, nice, intense, the extent to which we think people manifest our values. But that's changed very significantly. I will be disappointed if in the next no more than two months, not every one of our interviews has some strong AI native component to it.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“The obvious kind of tsunami coming is AI. Okay, what are the implications on jobs for that? I think there's been a lot of concern.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Scientist Richard Hamming, you and your research for any new graduate, probably the single best thing on a per word basis I think you can read, one of the central theses is find great people, work with them and learn from them. It sounds obvious, but there's something deeply correct. Like, how do we learn as human beings? We observe someone doing something and we effectively copy it. So find great people and copy them. That's how you accumulate skills and capabilities. And one of the other points Hamming makes in this talk is knowledge and hard work are like compound interest. And we all know the earlier you start saving because of the miracle of compounding interest, it can massively change the trajectory of your life. And so any young person should be intensely focused on learning as much as they can as early as they can, locking in those kind of lessons and capabilities, if you will, because it is.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“In particular, for a young company, I think it is, I won't say impossible, but very challenging to build a culture, a set of shared norms, camaraderie. I think so many of the things we talked about, enterprise software as a team sport, it feels great to be part of an amazing team. And it's different when your connection to that amazing team is via a Brady bunch of Zoom squares. We have rituals that we've developed that we only would have developed if we were all working in person. I think for younger employees, apprenticeship and mentorship that happens, so much of what I learned, and I think the initial conditions of my career were from experienced people taking me under their wing or letting me in cases literally look over their shoulder at how they were doing something. I think there's an element of paying it forward that's important and in person has a role to play in that as well. There's a talk that I love by the renowned computer.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I work a lot. Of course, if you just magically handed me 15 hours in a week that I wasn't with kids, I'd probably do something with those. I find I am intensely focused and efficient. And so like, boy, do I get a lot out of every hour I have? One of the things I've done, I spend a lot of time on 101 going to and from the office. We are all about in person and coming out of the pandemic. It was something of, you know, a novelty being opinionated about being in person. So I spent like an hour and a half, sometimes two, on the road every day. I now have a very complex networking setup that combines two cellular networks and a Starlink mini so that I have uninterrupted, beautiful connectivity to and from the city every day. You're efficient. You get everything that you can out of every hour.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Families. Our belief is that you can be part of something that is growing fast. You can be intense about your work. You can turn on the afterburners when you need. And it doesn't just mean kids. It's picking up your parents at the airport when they get in from out of town. It's going to the friend's extended birthday weekend. It's being, yes, at the parent-teacher conference or whatever it is. And I think there is too often an image of kind of a sometimes performative grind in certainly Silicon Valley startups. It's not that we don't believe in hard work. Like, boy, do we. Like, again, intensity, but it's in working smart and finding some balance that gives you space for, again, translate family to things that matter to you in the sense of your whole being beyond just work.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Each of our values comes directly from Bratt and me. And actually, one of the best decisions we made was, I think it was the time we were five or six employees. We spent half a day. Brett and I have a technique we call think apart, think together, where we'll initialize on a prompt. And the idea is not to group think one another. So we want to get kind of the best of our independent thinking. And so we did a think apart think together on values, went off and spent an hour kind of writing up what our view was, came back and compared notes. And there was, first of all, a shocking amount of overlap, which I guess shouldn't have in retrospect been surprising. It was like we had wanted to work together. We'd been friends. I think deeply similar in many of our values. Really, all of our core values, I would say. Family comes from, I've got four young kids. Brett's got three kids. And I married my high school sweetheart. And I think for both of us, the only thing that's more important than Sierra is our”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Japan is an interesting example of that. Why can't we have a giant business in Japan this year and not next year? What would have to be, oh, we would have to have like 10 people on the ground. I was like, why don't we buy a company there? You see how this stuff hangs together. Ambitious goals can take the form of a date, sure, date-driven development can sometimes work. I think also work is like a gas and tends to expand to fill all available space that you give it. And so there's a danger in setting dates as well. It's like, well, we've got this long. It may not need to take that long.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“You have to edit it. You have to have judgment for it. And I think you have to look at what is the thing that is not going to happen or won't happen as quickly without direct applied force from one of us or both of us. And so it's pointless to be in, quote, founder mode. 17 layers in the details and something that doesn't matter. It matters a lot if it's our next generation agent architecture and there's something that we can add. We try to be selective about where we engage at that level, but it's anything but kind of hands-off management. So I think it starts with the founder's ambitious goals have a way of becoming self-fulfilling. You set out a goal, whether it's the quality of a product or a revenue number. It's like, well, what would have to be true in order to get there? Like let's suspend disbelief and just imagine what would have to be true to cover this much ground this quickly. Why can't we do that? Okay, why shouldn't we?”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“500th engagement as intensely as we did our first. Like, you have to do that. And so I think there's also, I talk about the Venn diagram of who we hire for smart, nice, intense. And it's hard actually to get all of those three in a single person when you do, it's fantastic. You can feel it in the office. And another way of translating intensity is doing things with excellence, doing things with pace relates to craftsmanship as well.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“So, I think it's back to this great thing about giant market, giant market, hard thing about giant market, giant market, and others are in it too. I think there is an inevitability to companies interacting with their customers via really sophisticated agents that capture all that they know and all they can do on behalf of their customers and get the job done on their behalf that handle the complexity as opposed to pointing you to websites and so on, where the conversation is the interface. I think there's an inevitability to that. And therefore, in order to, when in order to build the best company in this space, it is about pace, it is about winning, it is about building the best product, it is about being competitive and being intense about it, knowing that we don't have the luxury of patience. Nothing written in the wind, right? That any particular company will be the company showing up in our fifth engagement and”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Working with us know how we will show up with their customers. A lot of it is how we show up with them, sweating the details in how we show up and interact with our customers, the level of professionalism, care, dropping everything when something matters. I'll give you an example there. In our first Black Friday Cyber Monday with a set of retailers, one of our lead engineers, our head of operations, me or Brett, was in real-time personally reading every single conversation that our agents were having. We wanted to make sure we were doing right by our customers. So that's craftsmanship. And again, adds up to a great company and it's, I think, very meaningful in helping our customers understand the care we will have for their customers.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I'll start with craftsmanship. Both Brett and I, just because of the way we are, we care about doing things well. If you're going to do something, do it with excellence. Two ways in which doing things with excellence mean much more than just sweating the details. One is what is a great company? A great company is an aggregation of thousands and thousands of things that are themselves great. It's great people. It's processes that are well designed. It's a great product. It's a great culture. And so how do you build an excellent company? Well, you build everything with excellence. And so I think holding ourselves to the standard, like if it is worth doing, it is worth doing well is one part of that because that adds up to a great company. How else do you get there? The other is you think about what our customers are trusting us with, back to the trust value, but I'll make the connection with craftsmanship. It is with their most precious asset. It is their customers. How will a company know? How will a set of people who are considering”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“It's generally been inbound, is the answer. We think about it honestly, not in terms of valuation. We think what is the amount of capital that we need to raise to get to the next unequivocally higher watermark in terms of revenue, company scale, and so on. So we think of it as like milestone to milestone funding. And then we're sensitive, but not maximally so to dilution. And so how do you balance those things? And every one of our rounds, we actually guided to and took a lower price than we could have.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“One early on was we had such good indicators of the demand we were going to see. And we just didn't hire fast enough to meet that demand. It was like, oh, like we could have taken on this additional set of customers. We had the data in front of us. Like we could see it and we didn't act decisively enough to build out a recruiting team, right? Like scale faster. This was early 2024. So early days in the company, we've since corrected, but that was one that stands out.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Clearly out onto paper, sending that in advance, giving each of our board members some kind of soak time to think through the issues and come prepared, rather than be like presented to and managed, I think is a big part of it. And then the contents of the board letters themselves, I think, is notable. We've done quite well in our first eight quarters and market. And generally, the format of a board letter is we exceeded forecast by a wide margin yet again. Things are going well. We landed these customers. Here are the seven things we think we could be doing better where we're unhappy. We could be going faster here, need to hire in this area and so on. And then the board meetings kind of take form on their own based on that. You get the scaffolding right. You get the people right. You get kind of setting the table of the big questions we're asking. And then genuinely, genuinely inviting our board members in to challenge us and improve and sharpen our thinking. Those are some of the ingredients.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“We do a couple things. You mentioned the six week cadence. We have kind of a TikTok, a three hour meeting, and a one and a half hour meeting. We've done this since the beginning of the company because we could just see if you're on the AI time clock, it moves a lot faster. Things are changing. Most recently, we came back from winter break and suddenly coding agents were amazing. You had Claude 4.5, Codex 5.2. There was a fundamental step change in the capabilities of these models. It changed our approach to software development. It changed our approach to the core product. And so having a cadence where you can take an information even from the last six weeks, update your priors, and then change course, I think is quite important. As for running the board meetings themselves, we don't have board decks. We have board memos. So Brett and I write a usually six to 10 page memo. There's a saying writing is just thinking on paper. And I think it's very hard to hide from writing. And so getting our thoughts.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“One of our approaches in building the company, and this kind of goes back to where we started, you can build a platform and hope that people come, right? The applications get developed on it, or you can build applications to inform a platform that makes building the third, fourth, and fifth that much easier. And so wherever we can, we're scanning for opportunities to strengthen our platform. So commonality is much better than something that is truly a one-off. That said, if we're working with a Fortune 50 or Fortune 20 or Fortune 10 or Fortune 5 company and there is some element of that company that is literally unique, of course we'll build that. And one of the neat things is it's actually become feasible to build that because of coding agents, because of the pace at which you can move. There's a real unlock there in being able to build a solution on an already deep platform, but extend it in ways that may apply to a single customer.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“First of all, Palantir is an amazing company. We have taken a lot of inspiration slash copied from them elements of our Ford deployed approach. My understanding is Palantir has kind of low hundreds of customers. We are and intend to be at a lot larger scale than that. And I think where that will come from in particular is building real domain expertise and specific industry verticals. You know, of course, our first, second, and third customer deployments were by definition unique, one of a kind. I think we've learned some things about how to help build a basket in the retail setting and in some of these other industries, how best to handle a question about the status of a healthcare claim, a healthcare insurance claim, or questions about a fee around a checking account. And so I think we're going to have these deeper and deeper lessons in specific industries and be able to apply those in a much”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Inbound and outbound. You're right. And it's not just Rocket Alone. Next, we worked with them on personalized product recommendations. How do you help someone build an outfit, a bigger basket of things they will love? Again, that's much more sales than support.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Think Rocket is actually a pretty good indicator of the direction that we're headed. You think about the life of a rocket customer, it begins with search and discovery of a home they might want to buy. We worked with Redfin to rethink their search experience. We help rocket reach out to folks who've expressed interest in a refinance, make contact that way. We worked with them to build rocket assist to help bring people in and help them shape and size their loan, gather all the information needed and so on. None of that is service and support. We do that, right? Loan servicing and so on. So I think that's a good example of where things are headed.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“There is effectively unbounded demand, I think, in two areas. One, we've talked about coding agents. The other is the space where we're the category leader. One of the reasons we've grown as quickly as we have is to meet that moment and meet that demand. We're now 100 people here in Europe. We recently acquired a company in Japan, Opera Technologies. You and I were talking about this, to hit the ground running there and to have a team that can be attuned to the cultural nuances of Japan and the concept of Omotanashi, which is extreme hospitality. That is what is expected in Japanese service. And that's what we intend to build there.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Generally, find though is in getting started having Sierra and help from our teams kind of drive while our customers in the passenger seat but navigating for the first version. It's what has enabled us to take companies like Next live in six weeks from kickoff to live behind their phone number and chat in six weeks or Cygna, one of the largest healthcare companies in the world live in, I think it was 58 days. And so time to market, time to impact, time to value, and then the quality of the result, we think it makes a big difference. I wouldn't say it's binary, though, as you framed it. I do think you can sell without a four deployed team. But I think for getting to the impact of this technology as quickly as possible and at the magnitude that we know is possible, boy, is it an important catalyst?”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Engineer Mihai was actually an employee of Weight Watchers, including getting its performance review time emails and so on. What we realized in that was no one has ever deployed an AI agent. No one has ever put AI in this way in front of their customers. And in order for us to build the best thing as quickly as we and our customers would like, being so close to the business, the mechanics of it, the people, their business model that we understand it, I won't say as well as our customers, but approaching that, we saw so much power in that. So starting in early 2024, we really started building out this forward deployed team. Customers use it in widely ranging ways. Our platform is highly extensible and very transparent. You can see exactly how an agent is built. You can export agent definitions and completely build your own. So no need for deployed if you don't want it.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I would like to think, at least in the AI space, I would say rediscovered and borrowed this model from Palantir. And we came to it almost accidentally. So we started the company. And the first thing we did was reach out to people we trusted to understand what are the biggest unsolved problems that you were looking at and saw, oh, interesting. Service and support as a foothold into something much broader, helping support customers across the entire life cycle. We then enlisted half a dozen design partners that we built the first version of our product and platform with and for. And these are in the history of the company, legendary companies, Olokai, SiriusXM, Sonos, Weight Watchers. We built the first version of our platform with our engineers deeply embedded inside those companies, so much so that our founding”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“It's hard to know, I think because the economies of scale in terms of depth and breadth of platform, experience in specific industry verticals and so on really compounds, my hunch is it will be more like an Uber lyft market. And we obviously think we're in the pole position to be the biggest.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I think, first of all, to state the obvious, the great thing about being in a giant market is this a giant market. The challenging thing about being in a giant market is it's a giant market and other folks know it too. And it's startups, it's longstanding companies, it's the incumbents. And so your point on it being competitive is certainly right. Five or ten years, especially in the age that we're in is a long time. I think what I had point to is amongst the startups, customers are voting with their feet. So we are at multiple larger size than our next nearest similar vintage startup competitors growing faster. As I said, are working with many of the great companies in the world.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Kind of simulate in our heads, but we're in the product. And then one of the things I think a lot about is we will, in short order, be in a way one of the larger B2C companies. We're doing that via our customers. We're serving hundreds of millions of interactions. Soon billions of interactions. So staying close to the end experience there as well, voice fluency, latency, the quality of the experience, all of that stuff is very energizing in things that we're close to. So I don't feel distant from the product, either from our customers' perspective or from their customers' perspective.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it's a little bit of a false choice you're implying there. I think being large enterprise doesn't necessarily mean you need to be distant from your customers in our case, our customers' customers. So Brett and I are constantly building agents ourselves. One of the more interesting things of the last six months, we released ghostwriter. This is an agent for building agents. It's kind of agents all the way down. It's pretty cool. But we are constantly in the products ourselves. And Brett is actually still an extraordinarily capable software engineer. It's remarkable. So some of the code that is in production, right, he has written, I've probably got a couple lines here or there, but pales in comparison. And so, of course, we can't on our own simulate the complex multi-system environments that characterize many of our largest enterprise customers so that we have to.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I would not bet on 3.8%. I would bet on much closer to 20%. In software engineering, the gains to me seem unequivocally there. You can debate, is it 2x, 10x, 20x, even if it's two acts? Okay, you've just effectively doubled the size of your engineering team. That's remarkable.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“We're not yet at that point. Our usage compared to some of those larger numbers is modest. And I think the benefit of learning at the fastest rate possible outweighs the capital discipline at this point. We prefer to learn quickly, see what works. It'll be interesting to see how the rate limiter in software development moves around how the Andy Grove breakfast factory, what is the, what is the constraining factor? It used to be writing code. Now it's probably reviewing code. Pretty soon it will be deciding what is worth building and editing kind of what could exist to what should exist. The dynamics there will be interesting.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Token max I think over the past six months, using a bunch of tokens was a proxy for you're using AI, you're leaning into it, you're trying to be more productive with it. So I think it's generally been a positive signal. I have heard and I have observed that top engineers who are really leaning in to cloud code, codecs, and so on are spending more than $100,000 on a run rate basis on tokens per year. That's a meaningful fraction of an engineering salary. So I think the direction that we're headed is some amount of token budgeting on a per-employee basis. I think for CFOs in the future, like capital allocation will look more like how do we allocate OPEX and then headcount and headcount will be both headcount for salaries and SBC and also tokens associated with headcount. And so here is your salary, here's your token budget have at it.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Sierra Brain is, it starts with a 20 or 30 page document that grounds any agent in what we are as a company, what we do, how we're organized, our team structure, the competitive landscape, our strengths and weaknesses, all of these things. On top of that, I've given it access to every one of our recent board letters, every one of our recent operating reviews, other insights and observations we have about what we believe to be true about the world. I can then use it to reason about what we should be doing as a company. And so it's a bit like a strategy thought partner, if you will, that knows the company, you know, if not inside and out very deeply.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“There are any instances of them. And it's kind of a shortcut to a faster, deeper read of every packet. So pine cone has just become this approaching indispensable. I think we're not quite there yet, but approaching indispensable tool for running the company.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Better reason, make decisions, get things done. Pine cone, of course, incorporates that MCP gateway, but then is a purpose built harness for all of Sierra. Pine cone knows how to build pinecon. There's a whole harness around the engineering of pine cone. And our engineers, there are phenomenally productive. We have a whole harness around the core of our platform, our agent architecture, agent studio where you build and deploy agents, speeding up software development there. And then we have a shared library of skills that anyone at the company can build. You can build one that's private to you. I have a whole bunch of skills, including one that is basically the clay scanner of interview packets. So I to date review and approve every single hire we make, and I get some help from Pinecone, and I've basically taught it what are the things that I look for? What do I scan for? Flag these.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. It's one of the more significant developments in how we run the company of the last six or nine months. And we began by building what we call our MCP gateway. This is a single MCP server that aggregates all of the main systems and services that we use to run the company. And so you can add this single gateway to your cloud instance, to your codecs instance, and indeed to PineCone. And basically via any one of those agents have full access with the permissions, of course, that you as an individual, the company, you can't read someone else's documents, but you can read your own, you can read your own Slack messages. And it's kind of like having superpowers, right? You can interrogate, in essence, the entirety of the company, all information that is published, whether it's Slack messages or presentations or operating reviews and so on, and use access to all of that information to”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“And to be able to sell and implement our product and solution successfully for organizations which are snowflakes. And so the process of selling and more importantly successfully implementing and deploying a solution like ours into the large enterprise is still a lot about deeply understanding our customers, business outcomes and objectives, about understanding their technology stack, integrating with it successfully, building relationships, earning trust to show up not just as a vendor that throws some software over the wall, but as a true partner in diffusing this technology into, in our case, all of the front office sales support, marketing, and so on.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the general direction of travel clearly is towards smaller higher leverage teams. We have software engineers who are completely AI pilled and using Claude Code, Kodaks, our own internal agent we call PineCone that we used to run much of the company on. They estimate they are between three and 20 times more productive in terms of features shift. The productivity gains certainly in software engineering and data science, data analysis, and other area we're seeing it in spades. But I think in time it will touch all parts of really every company. So that's the general trend. I think within a company like Sierra where we serve in particular the large enterprise, we work with 40% of the Fortune 50. We have 50% of our customers doing over a billion in revenue. We have 30% doing over 10 billion in revenue. These are some of the most complex and in cases regulated organizations in the world.”
2026-07-04 · The Twenty Minute VC · 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra · IDENTIFIED FROM THE TRANSCRIPT · source