Sierra

includes Sierra Brain

61 statements across 15 episodes · 30 bullish · 9 bearish · 10 people on the record · first statement Oct 2, 2024 by Bret Taylor · said 195 times in 50 episodes since 2024 · across every show →

Mentions by year, the whole family

brought up most by Harry Stebbings (100), Reggie Marable (21), Jason Lemkin (21), Clay Bavor (17), Rory O'Driscoll (12), Bret Taylor (4), Julien Bek (2), Winston Weinberg (1)

tap a year for its mentions
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01325202420252026episodes it came up in
002.513525202420252026episodesmentions per episode
2026 92 mentions in 25 episodes 4 per episode
2025 86 mentions in 21 episodes 4 per episode
2024 17 mentions in 4 episodes 4 per episode

every mention, scene by scene, with the transcript →

Everything said about Sierra, oldest first

Oct 2, 2024 bullish
Assertion Supported
Taylor: Sierra customers already use AI agents for sales and churn management
“Our customers already are using it for revenue generation, sales subscription churn management for subscription services, things like that.”
Bret Taylor Oct 2, 2024 ▶ 59:29 Bret Taylor: Why Pre-Training is for Morons & Companies Will Build Their Own Software | E1209 · 20VC with Harry Stebbings
Oct 2, 2024 positive
Assertion Supported
Bret Taylor only pitched Benchmark's Peter Fenton when fundraising for Sierra
“So when we started the company, I just called Peter Fenton, who I've worked with twice before. He's the only person I talked to.”
Bret Taylor Oct 2, 2024 ▶ 1:07:59 Bret Taylor: Why Pre-Training is for Morons & Companies Will Build Their Own Software | E1209 · 20VC with Harry Stebbings
Oct 2, 2024 bearish
Prediction Not checkable as stated
Taylor: Enterprise spending on AI professional services will drop as software matures
“I think there's probably some short term professional services spend that reflects the lack of the maturity of the AI applications market right now. You know, and I think that when there are solutions like Sierra and others for specific domains available, you …”
Bret Taylor Oct 2, 2024 ▶ 20:52 Bret Taylor: Why Pre-Training is for Morons & Companies Will Build Their Own Software | E1209 · 20VC with Harry Stebbings
Oct 2, 2024 positive
Disclosure
Bret Taylor: Sierra fine-tunes third-party models rather than pre-training
“So at Sierra, which is my company, we make a solution. We're not doing pre-training where, you know, we're fine tuning other people's models to build this solution.”
Bret Taylor Oct 2, 2024 ▶ 16:18 Bret Taylor: Why Pre-Training is for Morons & Companies Will Build Their Own Software | E1209 · 20VC with Harry Stebbings
May 2, 2025
Assertion Not checkable as stated
Sierra's Head of Sales and Co-Founders Prospect Every Single Day
“I still prospect every single day. Our co-founders prospect”
Reggie Marable May 2, 2025 ▶ 14:28 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Assertion Supported
Sierra's AI Agent Can Trigger SiriusXM Satellite Signal Resets for Cars
“If you're a serious XM customer, not only can we tell you what station shade 45 hip hop music is playing on, But we can also, if your radio stops working in your car, our agent will call the satellite and resend the encryption keys back to your car to get your…”
Reggie Marable May 2, 2025 ▶ 25:40 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Assertion Supported
Sierra Built Verticalized Sales Teams Unusually Early in Its Startup Journey
“Most companies wait until they get more scale and more maturity. At Sierra, we made the decision to do it early because we know those are the industries where we can make the most impact, and we really want to show up right in those industries by understanding…”
Reggie Marable May 2, 2025 ▶ 13:07 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 neutral
Disclosure
Sierra Credits Paid Proof-of-Concept Fees Toward Long-Term Enterprise Contracts
“The investment that you make in the proof of concept becomes a credit towards your long-term contract.”
Reggie Marable May 2, 2025 ▶ 10:55 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025
Assertion Not checkable as stated
Sierra's Enterprise AI Sales Cycle Averages Eight Months From First Meeting
“It's a little under a year. Because we are doing a proof of concept, which you've got to deploy the technology, build trust. It's AI. So you have to go through the legal compliance governance review. So it's about eight months from first meeting to actually cl…”
Reggie Marable May 2, 2025 ▶ 13:42 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Disclosure
Sierra Embeds a Dedicated Agent PM and Engineer in Every POC
“In all of our engagements, we don't just get you in a POC and walk away. It's a full service solution where we provide a dedicated agent product manager. Think of like ex Google MBA from Stanford, and then a dedicated agent engineer that's integrated that beco…”
Reggie Marable May 2, 2025 ▶ 17:29 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Disclosure
Sierra Structures Client Deals on Upsell Commissions and Churn Revenue-Shares
“We have one customer that actually pays us a commission when we upsell someone's membership, or we get paid when we prevent you from canceling. Some customers, we do a revenue share with them on, you know, preventing from someone from canceling their service.”
Reggie Marable May 2, 2025 ▶ 26:33 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Assertion Supported
Sierra Has Converted 100% of Its Paid Proof-of-Concept Clients
“I will knock on wood right now. We're batting a thousand on our proof of concepts.”
Reggie Marable May 2, 2025 ▶ 11:16 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025
Assertion Not checkable as stated
Sierra Conducts Real-Time Sales Call Postmortems With Two-Way Feedback
“Whether if we're in person, it's an in-person meeting, we'll just huddle right after, or if it's a virtual, we'll just jump on a Slack huddle and do it, but we do it Quick. And we provide each other feedback, good, bad, and ugly. And it's two way.”
Reggie Marable May 2, 2025 ▶ 50:04 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Disclosure
Sierra Runs Weekly Team Prospecting Blitzes Every Friday
“Every Friday we have like a quote unquote old school, like prospecting blitz where the team will block off a couple of hours. They'll do it together as a team to go out and prospect and try new, new strategies.”
Reggie Marable May 2, 2025 ▶ 44:58 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Opinion
Marable: Sierra Co-Founder Bret Taylor Is an "Apex Predator" Salesperson
“So I consider Brett one of the, I call him the apex predator. He's one of the best salespeople I've ever been around.”
Reggie Marable May 2, 2025 ▶ 7:19 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025
Disclosure
Sierra Absorbs All Implementation and Integration Costs for Enterprise Clients
“We don't charge implementation fees or any integration work. We absorb all of that.”
Reggie Marable May 2, 2025 ▶ 23:38 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 positive
Assertion Not publicly verifiable
Sierra Requires All Incoming Sales Leaders to Start as Individual Contributors
“At Sierra, what we do is everyone comes in as an individual contributor for a certain period, even if you were in leadership, like myself included.”
Reggie Marable May 2, 2025 ▶ 40:17 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025
Insight
Marable: Overriding Hiring Team Doubts on Sales Reps Always Backfires
“Over my, if I look at the statistics of folks that I've taken chances on that didn't work out, I always go back and look. I remember debating in that room, and there was two people that were like, I'm not sure, and we still did it anyways, and it came back to …”
Reggie Marable May 2, 2025 ▶ 38:50 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025 neutral
Assertion Not checkable as stated
Sierra Gathers Its Remote Sales Team in Person Once a Month
“Now we do have offices that, or people that work from home that don't live in those major cities, but I bring the sales team together once a month.”
Reggie Marable May 2, 2025 ▶ 47:03 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
Jul 31, 2025 bullish
Assertion Open · timeframe Jul 2025
Stebbings: Benchmark AI portfolio companies HeyGen, Sierra, and Fireworks hit $100M+ ARR
“McCaw over a hundred million in ARR. Hey Jen hitting a hundred million in ARR. Fireworks a hundred and forty million in ARR. Sierra with Brett Taylor over a hundred million in ARR.”
Harry Stebbings Jul 31, 2025 ▶ 5:24 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
Sep 11, 2025 negative
Opinion
O'Driscoll: Sierra's $10B valuation requires capturing labor budgets alongside software
“The only way the math works for the Sierra at ten billion is if you eat, you don't just get India, maybe not up front, but over time, you don't just get the service cloud revenue, you get the service cloud revenue plus some slug of the labor.”
Rory O'Driscoll Sep 11, 2025 ▶ 1:08:51 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 19, 2025 negative
Opinion
Zhang: Competitor Sierra relies on heavy, Salesforce-style configuration
“The approaches are just very different because of their leadership all coming from Salesforce. They've taken a very Salesforce-esque approach where it's, you know, the heavy configuration and sort of this longer lift to get going. And we're more of a, you know…”
Jesse Zhang Sep 19, 2025 ▶ 52:28 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
Sep 19, 2025 bullish
Opinion
Zhang: Decagon and Sierra will out-execute Salesforce on AI products
“I would expect a Decagon and a Sierra to be able to execute faster on a product side than Salesforce, but Salesforce has like so much distribution.”
Jesse Zhang Sep 19, 2025 ▶ 12:01 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
Nov 27, 2025 neutral
Insight
Rory O'Driscoll: Sierra must target $200B labor market to justify $10B valuation
“The only way this math works is if you eat a huge slug of the labor and because you eat the labor, instead of the, you know, twenty billion dollar software market for services, you eat the two hundred billion dollar a year services market for customer support …”
Rory O’Driscoll Nov 27, 2025 ▶ 39:48 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025 neutral
Insight
Rory O'Driscoll: Enterprise change management will limit Sierra's growth speed
“And I think the physics of diffusing this technology into the enterprise will be the rate limiter on how fast this company can grow. It won't be raw demand. It won't be the talent Of the CEO. It won't be the product. It will literally be, can you really roll o…”
Rory O’Driscoll Nov 27, 2025 ▶ 41:43 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025 positive
Disclosure
Rory O'Driscoll: Intercom's AI product growth rate is comparable to Sierra's
“I think they've done an amazing job in a way that very few SaaS companies have of transitioning to an AI first world, and the growth rate of their AI product is frankly comparable to Sierra's”
Rory O’Driscoll Nov 27, 2025 ▶ 46:19 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Feb 7, 2026 bearish
Opinion
Cohen: Sierra, OpenAI, and Anthropic Fail at Complex Vertical AI Needs
“There is nothing even remotely closed to what is needed when you go to a complex vertical out there. Okay. And it's definitely not in the kind of Sierra level, but even if you take it to the level of the APIs, If I'm kind of taking an anthropic and an open AI,…”
Ariel Cohen Feb 7, 2026 ▶ 21:00 20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen
Feb 12, 2026 bearish
Disclosure
O'Driscoll: Scale passed on direct competitors to Sierra and Decagon
“We looked at a number of companies that were behind Sierra and Decagon and came to the conclusion that a direct head-to-head Against those companies, when you're a smart, it's just a little bit too hard.”
Rory O'Driscoll Feb 12, 2026 ▶ 56:50 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Apr 2, 2026 neutral
Opinion
Stebbings: OpenAI should acquire Sierra and make Bret Taylor CEO
“It's the best thing for OpenAI not to buy Sierra, incorporate that as a customer support product, and have Brett Taylor come in as the day-to-day CEO, and Sam can be fundraiser, Sam can be master of...”
Harry Stebbings Apr 2, 2026 ▶ 15:33 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Apr 11, 2026 bullish
Disclosure
Reyna: ElevenLabs powers customer support AI competitors like Sierra and Decagon
“But I also think, like, you look at, like, all of our competitors, like, you mentioned Sierra, DecGone, and all of the other ones, we power all of them.”
Carles Reina Apr 11, 2026 ▶ 28:03 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
Apr 11, 2026 bearish
Opinion
Stebbings: AI customer support software is currently uninvestable due to competition
“I think customer support is uninvestable today, and I get so much shit on Twitter for this, because everyone shits on them, but I'm like, Sierra and Dakagon, obviously two market leaders in terms of brand, and how much money they've raised, and you've got 16 p…”
Harry Stebbings Apr 11, 2026 ▶ 26:52 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
May 7, 2026 bullish
Assertion Not checkable as stated
O'Driscoll: Sierra's LLM token spend is likely under 10% of its revenue
“And my guess is their LLM spend is sub-ten percent of revenues. In other words, LLMs are not the dominant portion of the value they deliver. It's the LLM plus the software, plus the whole thing, plus all the domain specific knowledge.”
Rory O'Driscoll May 7, 2026 ▶ 1:14:21 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 21, 2026 bearish
Prediction Not checkable as stated
O'Driscoll: OpenAI and Anthropic growth will stall unless enterprise software scales
“If Sierra doesn't grow, let me put it bluntly, if Sierra doesn't grow, then at some point, OpenAI and Entropic will stop growing because their customers today are primarily software companies for coding, right? And selling through software companies to corpora…”
Rory O'Driscoll May 21, 2026 ▶ 43:14 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
Jul 4, 2026 positive
Assertion Not checkable as stated
Sierra engineers report 3x to 20x productivity boost from AI agents
“We have software engineers who are completely AI-pilled and using Cloud Code, Codex, our own internal agent we call Pinecone that we used to run much of the company on, and they estimate they are between three and 20 times more productive in terms of features …”
Clay Bavor Jul 4, 2026 ▶ 16:50 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 bullish
Prediction Held up
Sierra expects to scale from hundreds of millions to billions of interactions
“We will in short order be in a way, one of the larger B to C companies. We're doing that via our customers, but you know, we'll, we'll, we're serving hundreds of millions of interactions, right? Soon billions of interactions.”
Clay Bavor Jul 4, 2026 ▶ 27:21 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Assertion Supported
Sierra hired creator of foundational ReAct agent paper as head of research
“Our first founding head of research was the Princeton professor who literally wrote the paper on language model based agents, the react paper.”
Clay Bavor Jul 4, 2026 ▶ 5:23 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Assertion Not checkable as stated
Sierra uses six-to-ten-page written memos instead of decks for board meetings
“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.”
Clay Bavor Jul 4, 2026 ▶ 39:52 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Disclosure
Bavor built an internal AI strategy partner trained on Sierra board letters
“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. And then on top of th…”
Clay Bavor Jul 4, 2026 ▶ 21:12 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Assertion Supported
Sierra gives engineering candidates $150 in tokens for AI-native interviews
“We completely changed our engineering interview process. So it now looks much more like, here's a very here's a kind of prompt think through an application you would like to build. Cool. Okay. Here's a 150 dollars to spend on choose your coding agent. You can …”
Clay Bavor Jul 4, 2026 ▶ 57:58 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Disclosure
Sierra deliberately took lower valuations than offered in every funding round
“Every one of our rounds, we actually guided to and took a lower price than we could have.”
Clay Bavor Jul 4, 2026 ▶ 0:36 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Assertion Not checkable as stated
Bavor: Sierra holds board meetings on a six-week cadence
“You mentioned the six week cadence. We have kind of a tick tock, a three hour meeting and a one and a half hour meeting. We've done this since the beginning of the company”
Clay Bavor Jul 4, 2026 ▶ 39:08 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Assertion Not checkable as stated
Sierra founders personally monitored every AI customer conversation during Black Friday
“When we, in our first Black Friday, Cyber Monday with a set of retailers, one of 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, because we wanted to mak…”
Clay Bavor Jul 4, 2026 ▶ 45:04 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Disclosure
Sierra builds proprietary fine-tuned models on top of open weights
“So today we have a set of our own proprietary fine tune models. But these are fine tunes on top of open weights models.”
Clay Bavor Jul 4, 2026 ▶ 6:50 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Assertion Not checkable as stated
Bavor uses dual cellular and Starlink Mini for uninterrupted commute connectivity
“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.”
Clay Bavor Jul 4, 2026 ▶ 53:04 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 negative
Prediction Open · timeframe Jul 2031
Sierra will not pre-train foundation models, leaving capex to major AI labs
“And we're not, you know, we're not doing our own pre-training. We'll leave the capital expense there to, you know, the labs and the larger companies.”
Clay Bavor Jul 4, 2026 ▶ 5:40 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 bullish
Prediction Open · timeframe Jul 2029
Sierra aims for far greater customer volume than Palantir
“My understanding is, you know, Palantir has kind of low hundreds of customers. We are and intend to be at a lot larger scale than that.”
Clay Bavor Jul 4, 2026 ▶ 36:17 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Insight
Bavor: Co-founders should use a 'majors and minors' responsibility framework
“We think about rather than dividing up the company, we think about Majors and minors for every part of the company.”
Clay Bavor Jul 4, 2026 ▶ 1:01:09 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Assertion Not checkable as stated
Sierra co-founder Bret Taylor still writes production code for the startup
“Brett is actually still an extraordinarily capable software engineer. It's remarkable. So, you know, some of the code that is in production, right, he has written”
Clay Bavor Jul 4, 2026 ▶ 26:45 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Prediction Not checkable as stated
Bavor: Every Sierra job interview will be AI-native within two months
“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.”
Clay Bavor Jul 4, 2026 ▶ 58:46 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Assertion Partly supported
Bavor: 50% of Sierra's enterprise customers generate over $1B revenue
“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 ten billion in revenue.”
Clay Bavor Jul 4, 2026 ▶ 17:24 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 bullish
Assertion Not checkable as stated
Bavor: Sierra is multiple times larger than its closest startup competitor
“We are at multiple larger multiple larger size than one of our next nearest similar vintage startup competitors growing faster.”
Clay Bavor Jul 4, 2026 ▶ 29:06 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026
Assertion Not checkable as stated
Bavor personally reviews and approves every single hire at Sierra
“So I, to date review and approve every single hire we make, and I get some help from pine cone and I've basically taught it.”
Clay Bavor Jul 4, 2026 ▶ 20:35 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 neutral
Disclosure
Clay Bavor details recent operational debate with Sierra co-founder Bret Taylor
“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 and maybe we need different leaders or a different leader in this space. The answer is with most things like turned out to b…”
Clay Bavor Jul 4, 2026 ▶ 1:00:21 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 negative
Insight
Bavor: Pre-training foundation models is economically unviable for most startups
“The capital expense the ongoing capital expense to create what is effectively a highly perishable bag of floating point numbers just doesn't work. Just doesn't work for any, but a small number of companies.”
Clay Bavor Jul 4, 2026 ▶ 6:13 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 bullish
Prediction Not checkable as stated
Bavor: Enterprise AI will be a duopoly with Sierra in the lead
“My hunch is it will be more like an Uber lift market. And we obviously think we're in the pole position to be the bigger of those two.”
Clay Bavor Jul 4, 2026 ▶ 29:42 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Disclosure
Sierra built its initial platform embedded inside Weight Watchers, Sonos, and SiriusXM
“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, legendary companies. Olokai, great flip-flops, you should buy them. SiriusXM, Sonos…”
Clay Bavor Jul 4, 2026 ▶ 30:39 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Jul 4, 2026 positive
Assertion Not checkable as stated
Bavor: Sierra's most effective employees are 22- to 23-year-olds
“Some of our most effective employees of the entire company are 22 or 23 years old and have been completely AI-pilled.”
Clay Bavor Jul 4, 2026 ▶ 0:40 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
Sep 5, 2026 neutral
Assertion Supported
Weitzman: Sierra relies on third-party models and Bret Taylor's go-to-market
“Sierra doesn't have their own model team. They use other people's models, right? Because the value of Sierra is the go to market. It's Brett Taylor.”
Cliff Weitzman Sep 5, 2026 ▶ 51:13 How to Build Your Own Data Center & Why Every Startup Should Do It
Sep 5, 2026 neutral
Insight
Weitzman: Sierra's core value is tool calling, unlike ElevenLabs
“If you use a tool like Sierra, the wedge right now is voice, but the important part is tool calling. 11 Labs lets you do some tool calling, but that's not the bread and butter.”
Cliff Weitzman Sep 5, 2026 ▶ 54:40 How to Build Your Own Data Center & Why Every Startup Should Do It
Sep 5, 2026 bullish
Opinion
Stebbings: Bret Taylor is building Sierra to recreate the next Salesforce
“I think Brett Taylor's actually trying to recreate the next generation of Salesforce. He is absolutely not playing the customer support game. He's moving into pre-sales.”
Harry Stebbings Sep 5, 2026 ▶ 54:13 How to Build Your Own Data Center & Why Every Startup Should Do It
Sep 10, 2026 neutral
Opinion
O'Driscoll: Sierra must become a complete customer ecosystem to justify massive valuation
“The only way I can justify 15 or twenty billion in market cap for Sierra is not if I build a slightly better next generation service cloud, if I am the entire customer ecosystem for your entire business.”
Rory O'Driscoll Sep 10, 2026 ▶ 1:14:37 Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town
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