Sierra, every mention

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every year anyone Harry Stebbings 100Reggie Marable 21Jason Lemkin 21Clay Bavor 17Rory O'Driscoll 12Bret Taylor 4Julien Bek 2Winston Weinberg 1Vlad Tenev 1Scott Wu 1

Verbatim, from the transcripts: the passages where Sierra comes up

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Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town Sep 10, 2026 · 4 mentions

  • ▶ 1:08:12 Jason Lemkin First, huge kudos to going from like the multilingual Sierra Decagon to like, uh, the, the, the team of 650 folks helping you deploy AI in the enterprise. 4 times in the scene

How to Build Your Own Data Center & Why Every Startup Should Do It Sep 5, 2026 · 14 mentions

  • ▶ 24:50 Cliff Weitzman Sierra has this concept called outcome-based pricing.
  • ▶ 25:32 Harry Stebbings You are now competing against 11 Labs and Sierra, really, and those two are competing. 4 times in the scene
  • ▶ 50:22 Harry Stebbings You have Sierra and Dak gone out in front with the majority of funding and attention, but to say that there are 18 companies that have now raised over a hundred million in the last 18 months, uh, there is, uh, kind of what I would call,… 4 times in the scene
  • ▶ 53:29 Harry Stebbings What will be a bigger company in five years, Sierra or 11 Labs? 5 times in the scene

NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation Sep 3, 2026 · 1 mention

ClickHouse CEO: AI Margins Need to Improve | Revenue Concentration Should be a Concern Aug 31, 2026 · 1 mention

  • ▶ 48:09 Aaron Katz The basket of AI companies that's using us in nearly every AI companies built on ClickHouse from Harvey, Sierra, Decagon, Anthropic, OpenAI, et cetera, represents less than 12% of revenue.

Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek Aug 24, 2026 · 2 mentions

  • ▶ 1:08:48 Julien Bek And the way it works is, you know, we have a company called Sierra. 2 times in the scene

Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings Jul 4, 2026 · 29 mentions

  • ▶ 0:13 Harry Stebbings Clay Bavor joining me in the hot seat, co-founder of Sierra, one of the fastest growing AI companies in the world. 3 times in the scene
  • ▶ 1:37 Harry Stebbings Um, so I want to start with, I heard that Brett tried to hire you or start a company with you several times before Sierra.
  • ▶ 4:06 Harry Stebbings What are your single biggest takeaways from that experience that you took with you to Sierra, and what did you leave behind? 3 times in the scene
  • ▶ 16:19 Harry Stebbings Says, well, if you're Sierra, you can't do that. 4 times in the scene
  • ▶ 19:56 Clay Bavor Purpose built harness for all of Sierra. 6 times in the scene
  • ▶ 21:06 Clay Bavor Uh, I've been working on what I call Sierra brain and, um, some other things. 3 times in the scene
  • ▶ 32:16 Clay Bavor What we generally find though is in getting started, having Sierra and help from our teams kind of drive while our customer is in the passenger seat, but navigating for the first version. 2 times in the scene
  • ▶ 34:31 Harry Stebbings Is Sierra a sales platform in the future?
  • ▶ 41:54 Clay Bavor So early days in the company, you know, we've since corrected, but that was one that stands out. 3 times in the scene
  • ▶ 51:10 Clay Bavor Uh, and I think for both of us, the only thing that's more important than Sierra is our families.
  • ▶ 57:35 Clay Bavor Some of our most effective employees at the entire company are 22 or 23 years old and have been completely AI pilled and have a
  • ▶ 1:11:10 Clay Bavor Uh, wonderful 18 years at Google, starting Sierra, and today.

DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings Jun 25, 2026 · 1 mention

  • ▶ 10:23 unnamed speaker How do you let people work on what they want to work on when you need the chat bug fix so you can compete with Sierra?

Anthropic's Fable Banned by US Government | Wix & Adobe Hit All-Time Lows | Mistral Raising at $20BN · 20VC with Harry Stebbings Jun 18, 2026 · 2 mentions

  • ▶ 46:54 Everett Randle You know, the Sierras and Fireworks and Lagoras and Mercores and Langchains and Haygens of the world in that fund, um, and, and many others as well, and so the, the funds look, the funds obviously, um, look, look awesome, but, um, but no,…
  • ▶ 52:15 unnamed speaker Right, because they're competing against, you know, one of your very best companies, Sierra.

SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings Jun 11, 2026 · 1 mention

  • ▶ 45:38 Harry Stebbings Don't worry, I hate to say it, it's not just, I mean, it's Lagorre, it's Harvey, it's your Sierras.

Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings May 21, 2026 · 1 mention

  • ▶ 43:14 Rory O'Driscoll And if, you know, if Sierra doesn't grow, let me put it bluntly, if Sierra doesn't grow, then at some point, OpenAI and Tropic will stop growing because their customers today are primarily software companies for coding, right?

Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings May 18, 2026 · 1 mention

Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings May 14, 2026 · 2 mentions

  • ▶ 31:04 Jason Lemkin They're not going to rebuild Decagon or Sierra or Finn or gorgeous or any of these other, it's not that they won't build chunks of it.
  • ▶ 1:05:11 Jason Lemkin You know, but we don't need any, we don't, why would I, why would I go see, uh, Andrew when, uh, when he was on 20 VC and was better from Sierra, but like, so we don't, we have no firesides and no speaker.

Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings May 7, 2026 · 13 mentions

  • ▶ 0:26 Harry Stebbings In private markets, Sierra raising nine hundred and fifty million dollars at a fifteen billion dollar valuation.
  • ▶ 30:16 Rory O'Driscoll And they're really good at saying, you know, let's take Sierra. 2 times in the scene
  • ▶ 48:31 Jason Lemkin But Sierra, fifteen billion dollar, run on, run on Twilio, right? 2 times in the scene
  • ▶ 1:12:37 Rory O'Driscoll If you're selling a story that says we're going to replace the old customer support software with new, you know, you're going to replace Service Cloud, which is the Salesforce product, which Brett Taylor obviously knows really well with… 4 times in the scene
  • ▶ 1:17:21 Harry Stebbings If you were to put a dollar to work, Sierra or Anthropic? 4 times in the scene

The Early Days of Anthropic & How 21 of 22 VCs Rejected It | The Four Bottlenecks in AI | Anj Midha · 20VC with Harry Stebbings Apr 14, 2026 · 1 mention

  • ▶ 53:30 Harry Stebbings So they can offer the best customer support and then sell their older models to Sierra and Decagon so they have a worse quality model retaining the best for themselves.

ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings Apr 11, 2026 · 2 mentions

  • ▶ 26:52 Harry Stebbings I think customer support is uninvestable today, and I get so much shit on Twitter for this, because everyone shits on them, but, but I'm like, Sierra and Dakagon, obviously two market leaders in terms of brand, and how much money they've…
  • ▶ 28:03 unnamed speaker Um, 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.

OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings Apr 2, 2026 · 1 mention

  • ▶ 15:36 Harry Stebbings 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...

NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings Mar 19, 2026 · 1 mention

  • ▶ 40:05 Jason Lemkin It's easy to be, take any, I mean, I, I, I, I, I'm getting bored of talking about the same companies, but to have a thread through our conversation, certainly I, I wouldn't have believed that being in this space, having made so many…

Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings Mar 16, 2026 · 1 mention

Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings Mar 12, 2026 · 3 mentions

Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings Mar 5, 2026 · 1 mention

  • ▶ 29:49 unnamed speaker If Sam left, you buy, you buy Sierra for 80,000,000,010 percent of the value and you buy out the shareholder, you know, whatever the math works, whoever gets what you do, you just do it overnight for eighty billion and your problem is…

Insights from Coatue's Growth Investor Lucas Swisher · 20VC with Harry Stebbings Feb 23, 2026 · 1 mention

Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings Feb 12, 2026 · 4 mentions

  • ▶ 45:57 Harry Stebbings Customer support is one I just cannot get my head around, and I, I know that sounds ridiculous and, and very, uh, basic, but when you look at the sheer number of players that have been funded to huge extremes, and we saw Sierra's fifty… 4 times in the scene

a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings Feb 9, 2026 · 1 mention

  • ▶ 31:30 Harry Stebbings With your Decagons, and your Sierras, and your Intercoms, and your Poloas, and I can go on and on.

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 7, 2026 · 2 mentions

  • ▶ 20:48 Harry Stebbings Why did you decide to do a build versus buy and work with a Brat Taylor at Sierra or a Jesse at Dakagon? 2 times in the scene

Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings Jan 19, 2026 · 2 mentions

  • ▶ 26:44 Winston Weinberg And the problem that you're going to end up happening is you have these vertical companies building vertical agents like us and Sierra, et cetera.
  • ▶ 33:50 Harry Stebbings This is what I worry about, though, when I look at kind of, when you look at GRR figures, and you think about like a Sierra, and it's like the growth, and Brett's amazing, and like the best of the best, Jesus, like, take my money too,…

Matt Fitzpatrick: Who Wins the Data Labelling Race & Why Al Needs Forward-Deployed Engineers · 20VC with Harry Stebbings Dec 31, 2025 · 1 mention

  • ▶ 15:48 Harry Stebbings How am I meant to understand whether we go for Sierra or Decagon or Zendesk of old or Intercom or, or any of the other players that we've seen in the space?

Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings Dec 22, 2025 · 1 mention

a16z's David George on the Most Controversial Bet at a16z & Do Margins and Revenue Matter in AI? · 20VC with Harry Stebbings Dec 15, 2025 · 2 mentions

SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings Dec 11, 2025 · 5 mentions

  • ▶ 53:58 Harry Stebbings I think this actually goes back to our discussion about Sierra's implementation within enterprise, which I've seen with Solve. 4 times in the scene
  • ▶ 1:00:58 Rory O'Driscoll In fact, Sierra did an interesting piece on how a lot of their application is a constellation of models.

Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings Nov 27, 2025 · 10 mentions

Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings Nov 24, 2025 · 1 mention

  • ▶ 6:10 Harry Stebbings Maybe a tiny, tiny portion, or build your own intercoms, or Sierras, or Decagons, and then do maintenance and updates.

Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings Nov 10, 2025 · 1 mention

  • ▶ 35:29 Harry Stebbings To your Lagoras, to your Langchains, to your Sierras, to your Macaws, to your Firework, to, I mean, like, we're focused on cash on cash.

Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings Nov 6, 2025 · 1 mention

  • ▶ 58:29 Jason Lemkin At the same time, what we're all learning now, we feel like it's late with all the stuff we talked about, the cursors and replets and levels and Sierras, but it's actually so early in so many categories, right?

Why VC Today is Worse than 2021 · 20VC with Harry Stebbings Oct 23, 2025 · 1 mention

  • ▶ 17:39 Jason Calacanis But we're funding, we're funding Sierra at fifty million, ARR at ten billion, assuming, what's the assumption, uh, Rory, that that will hit ten billion ARR in five years or something?

Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings Oct 16, 2025 · 1 mention

  • ▶ 51:11 unnamed speaker Oh, Sierra is amazing.

20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan Oct 10, 2025 · 1 mention

  • ▶ 18:16 Harry Stebbings Well, in that time, Lovable and Rapplet and Brett and Sierra and everyone in between have scaled to a hundred million dollars.

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 · 4 mentions

  • ▶ 11:49 Harry Stebbings Do you feel like you're in a line grab against Sierra though, in the same way that Lovable is with Ratplit or Harvey is with Lagora? 4 times in the scene

OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings Sep 11, 2025 · 10 mentions

  • ▶ 24:35 Harry Stebbings When we look at like a Brex, last round was thirteen billion, now seven hundred million growing 50%, and then you look at a Sierra, ok, I love Brett Taylor, phenomenal operator, interviewed him before, to not compete with Brett Taylor was…
  • ▶ 25:19 Jason Lemkin The, the, the, the, the, the hundred X, but I think, I mean, Brett Taylor, if you buy Sierra, you get everything, right? 7 times in the scene
  • ▶ 1:01:18 Jason Lemkin Well, you can't buy Sierra.
  • ▶ 1:08:51 Rory O'Driscoll 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…

Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings Jul 31, 2025 · 1 mention

Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 20VC with Harry Stebbings Jul 18, 2025 · 1 mention

  • ▶ 40:34 Scott Wu And then if you take all the application layer companies, you know, it's, the, the top ones that come to mind are, you know, there's Perplexity, there's Sierra, there's Dekagon, there's Harvey, there's Us, there's Kerser, there's, you know,

Robinhood Founder & CEO, Vlad Tenev: Robinhood’s $85BN Resurgence & Tokenizing SpaceX & OpenAI · 20VC with Harry Stebbings Jul 14, 2025 · 1 mention

  • ▶ 4:10 Vlad Tenev Um, well, first of all, when we started, the off the shelf companies like Sierra, for instance, they were just getting off the ground.

Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings Jun 26, 2025 · 1 mention

  • ▶ 1:06:42 unnamed speaker Eliminate 20% of your service center personnel, and the resolution rate with some third party product, like Decagon, Finn, Sierra, is 50 or 60%, then you're going to lose business pretty quickly.

Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings May 8, 2025 · 4 mentions

  • ▶ 54:15 Rory O'Driscoll With Sierra, they've established an interesting need in the kind of, some of those early spaces.
  • ▶ 54:54 Harry Stebbings You mentioned Sierra.
  • ▶ 1:01:36 Rory O'Driscoll New companies trying to do it, but I'm going to say, let's say, let's say Decagon and Sierra, yeah, we have observed in the foreign side of it, two or three of them make critical mass and explode, right? 2 times in the scene

20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI May 2, 2025 · 36 mentions

  • ▶ 0:10 Harry Stebbings Today we have one of the best, Head of Global Sales for one of the fastest growing AI companies in the world, Sierra, founded by Brett Taylor and funded by Benchmark and Greenos. 2 times in the scene
  • ▶ 6:13 Harry Stebbings And what I mean by that is, when you think about your role with Sierra State, what did you see at Salesforce and deliberately decide to not bring with you? 6 times in the scene
  • ▶ 8:20 Reggie Marable What executives of Sierra are getting involved in your deal cycle?
  • ▶ 10:12 Reggie Marable One of the things that we do at Sierra is we do a proof of concept. 3 times in the scene
  • ▶ 12:14 Reggie Marable That's where Sierra wants to be. 2 times in the scene
  • ▶ 14:41 Reggie Marable I can't speak for other heads of sales, but I know I will take out the trash and wash the dishes if it helps Sierra be successful.
  • ▶ 19:42 Reggie Marable And these are some, some of our like super, super sharp people that we've been able to attract and work at Sierra.
  • ▶ 23:42 Reggie Marable So when you partner with Sierra, you're paying for outcomes, you're paying for results.
  • ▶ 24:38 Harry Stebbings It wasn't really Sierra doing that work. 2 times in the scene
  • ▶ 28:22 Reggie Marable I try to use, and I, and I think our teams, one of our mantras at Sierra is use the technology to make the way we operate better. 2 times in the scene
  • ▶ 30:58 Harry Stebbings What were the hardest elements of building out the sales team at Sierra when you joined as employee number 23? 4 times in the scene
  • ▶ 36:32 Harry Stebbings The presentation, sorry, just to dive in there, are they about Sierra, or are they about a company they've worked with before?
  • ▶ 40:17 Reggie Marable 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. 4 times in the scene
  • ▶ 48:53 Reggie Marable It's, it's something we truly believe in at Sierra is craftsmanship.
  • ▶ 52:57 Reggie Marable Are you leveraging the power of your, of Sierra? 2 times in the scene
  • ▶ 1:00:21 Reggie Marable But I think, uh, based on the power of what we can do for clients at Sierra, I'm hopeful that we'll have much bigger transactions. 3 times in the scene

Benchmark GP, Victor Lazarte: The 3 Traits All the Best Founders Have · 20VC with Harry Stebbings Apr 14, 2025 · 1 mention

20Product: How to Design and Build Products in a World of Agents | Why AI Will Kill Many SaaS Products | What Products Will Thrive and Die in a World of 100M Developers with Matt Biilmann, Co-Founder and CEO @ Netlify Mar 14, 2025 · 2 mentions

  • ▶ 3:20 Harry Stebbings Perplexity, Vercel, Sierra, I mean, these companies are awesome, and they've raised ninety-five million dollars in funding from amazing people like TwentyVC.
  • ▶ 48:01 Harry Stebbings Perplexity, Vercel, Sierra.

Guy Podjarny: The Future of AI Software Development - What is Real & What is BS | E1232 · 20VC with Harry Stebbings Nov 29, 2024 · 1 mention

Bret Taylor: Why Pre-Training is for Morons & Companies Will Build Their Own Software | E1209 · 20VC with Harry Stebbings Oct 2, 2024 · 9 mentions

  • ▶ 16:18 unnamed speaker You know, so at Sierra, which is my company, we make a solution.
  • ▶ 19:19 Bret Taylor I think that's what companies like mine are doing is essentially 2 times in the scene
  • ▶ 39:26 Bret Taylor So I had a thesis when we started Sierra, uh, in, in March of last year, that eventually we'd end up with a few, a frontier model, uh, frontier models, essentially, uh,
  • ▶ 44:42 Harry Stebbings First off with Sierra, why did you can literally do anything? 4 times in the scene
  • ▶ 54:06 Bret Taylor Uh, approximating this already, but I think, you know, large language models and agents like the ones we build at Sierra open the door to sort of much more full featured experiences.
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