Sierra

company on 23 shows · 118 statements across 51 episodes · said 468 times in 158 episodes since 2024

20VC 192 Latent Space 39 No Priors 37 Big Technology 30 Acquired 28 the Knowledge Project 28 Lenny's Podcast 28 Cheeky Pint 18 the Neon Show 14 Invest Like the Best 10 the Official SaaStr Podcast 8 Sourcery 7 the a16z Podcast 7 TBPN 6 A Product Market Fit Show 5 the MAD Podcast 3 All-In 3 BG2 Pod 2 the Y Combinator Startup Podcast 1 David Senra 1 Top Founders 1 More or Less Masters of Scale

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20VC 192Latent Space 39No Priors 37Big Technology 30Acquired 28the Knowledge Project 28Lenny's Podcast 28Cheeky Pint 1813 more shows

2026 229 mentions in 84 episodes 3 per episode
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2024 58 mentions in 18 episodes 3 per episode

every mention on every show, scene by scene, with the transcript →

The latest 60 statements about Sierra, every show

20VC 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
20VC 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
20VC 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
20VC 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
NEON SHOW Assertion Supported
Jain: Customer service AI startups like Sierra emerged post-ChatGPT
“And then chat GPT happened and then everyone realized actually customer service is going to be the biggest market for AI. And they've been on the journey since then. You know, I think in customer experience in customer service, Sierra, Decagon, everything happ…”
Swapnil Jain Aug 14, 2026 ▶ 10:04 ChatGPT Killed My $50M ARR Business Overnight | Swapnil Jain Observe Al
NEON SHOW Prediction Not checkable as stated
Jain: High probability customer service AI startup Sierra gets killed
“There's a very high chance Sierra will get killed.”
Swapnil Jain Aug 14, 2026 ▶ 45:03 ChatGPT Killed My $50M ARR Business Overnight | Swapnil Jain Observe Al
NEON SHOW Assertion Not checkable as stated
Jain: Sierra and Decagon's reported ARR is contracted, not deployed at scale
“And the reality of a lot of, in full reality, a lot of the so-called ARR that you see with some of these companies that you mentioned is actually contracted ARR. So none of this is ever actually deployed in production at scale. Find me one real customer from a…”
Swapnil Jain Aug 14, 2026 ▶ 45:32 ChatGPT Killed My $50M ARR Business Overnight | Swapnil Jain Observe Al
a16z Assertion Not checkable as stated
Zhang: Decagon's most recent customer churned from competitor Sierra
“Our most recent customer actually turned off of Sierra to come to Decagon”
Jesse Zhang Jul 30, 2026 ▶ 38:36 How Decagon Runs 90% of Its Agents on Open-Source Models
ALL-IN Assertion Not checkable as stated
Leyora scaled from $1M to $150M ARR faster than Sierra
“So I think we actually just became as of the close last week on Tuesday, one of the fastest enterprise company with a direct sales motion to grow from one to 100 and 150. Bidding Sierra with one quarter.”
Max Junestrand Jul 14, 2026 ▶ 32:01 The Trillion-Dollar Industries AI Is Disrupting: Voice, Law & the End of the Billable Hour
LATENT SPACE Prediction Not checkable as stated
Swyx: Specialized agent labs like Cursor, Cognition, and Harvey will endure
“There will always be capability overhangs. They may not stay still, and so you gotta be nimble. But the Sierras of the world, the Cognitions of the world, the Cursors of the world, the Decagons and Harvey's, these are all agent labs for their field. They can b…”
Shawn Wang Jul 10, 2026 ▶ 23:47 Podcast Crossover: AIE, AGI, frontier lab strategy with ​ ⁨@matthew_berman⁩ and @swyxtv
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
SAASTR Insight
Lemkin: AI support, sales, and marketing functions are converging into one agent
“If you talk to folks like at Finn or Intercom or Gorgias or Sierra and others, they're all saying that there's convergence that support sales and marketing are all converging because once you can AI-ify them, you don't want to have three different agents, righ…”
Jason Lemkin Jun 16, 2026 ▶ 18:57 Our Agent Negotiated a Vendor Renewal, Became a CFO and a Better SDR .. but has too many guardrails
SAASTR Opinion
Lemkin: AI Agents Expanded Customer Support and Legal SaaS Markets 100x
“These Sierra Decagons, and also legal Harvey, these were niche markets before agents. These were niche markets that are like 10 to a hundred times larger because the agents add so much value.”
Jason Lemkin Jun 11, 2026 ▶ 47:52 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
NEON SHOW Assertion Partly supported
Ahluwalia: Sierra and Decagon are valued at nearly $10B
“Customer support has companies like Sierra, Decagan, Which are already almost ten billion dollar companies.”
Siddhartha Ahluwalia Jun 9, 2026 ▶ 25:39 94% CAGR: What the Inference Boom means for your AI costs | Vamshi Ambati
NEON SHOW Prediction Not checkable as stated
Ambati: Sierra and peers will soon solve AI empathy and intervention
“And I'm betting that I'm, companies like Sierra and others will figure this out soon. But if they don't, then I think the spike has to come down.”
Vamshi Ambati Jun 9, 2026 ▶ 26:39 94% CAGR: What the Inference Boom means for your AI costs | Vamshi Ambati
20VC 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
Kahlow: Customer support AI platforms operate as low-margin businesses
“They're solving the problem of, you know, solving support cases and tickets. That is a very low margin business, right? So, like, you can't have a million conversations and have it cost a lot because there's not a big upside to that.”
Amanda Kahlow May 13, 2026 ▶ 22:54 How 1Mind Hit $1M in 3 Months Selling $100k AI Sales Agents
20VC 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
NO PRIORS Prediction Not checkable as stated
Herzig: AI will transition software pricing to consumption, then outcome-based models
“Very clearly with AI, it was very clear for us that, you know, step by step, it will go towards this consumptive world, right? First consumptive, and then maybe in the next step, once we have more verifiability in the system, then also towards maybe an outcome…”
Philipp Herzig Apr 23, 2026 ▶ 34:48 SAP: Bringing the ‘Operating System’ of a Company into the AI Era with CTO Philipp Herzig
Kantrowitz: Combining Bret Taylor's Sierra and OpenAI makes perfect sense
“And by the way, Brett Taylor, a combination of Sierra and open AI would make so much sense, especially as open AI goes after goes after enterprises. It would be a perfect match.”
Alex Kantrowitz Apr 20, 2026 ▶ 46:09 Jensen On The Ropes, Sam Altman’s Conflicts, Allbirds’ GPU Pivot
20VC 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
20VC 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
20VC 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
PRODUCT MARKET FIT Assertion Supported
Sierra suffered a massive AI agent failure with Gap
“There was a massive hiccup with AI agents that Sierra launched for Gap.”
Roy Moussa Mar 12, 2026 ▶ 21:12 This 3x founder hit $1M ARR in 5 months. Here's his playbook. | Roy Moussa, Founder of GetVocal · PMF Show
CHEEKY PINT Assertion Not checkable as stated
Taylor: Sierra AI agents are calling each other in English over PSTN
“So, we have payers with AI agents that pick up the phone. And we have providers that have AI agents that pick up the phone and make phone calls. We have revenue cycle management companies that work to make outbound calls to do it. We've already had- ... We've …”
Bret Taylor Mar 10, 2026 ▶ 17:11 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT Assertion Supported
Taylor: Sierra raised SoFi's Net Promoter Score by 33 points
“We just did a great case study with SoFi and I'm really proud that we raised their net promoter score by 33 points, just because it's just so delightful.”
Bret Taylor Mar 10, 2026 ▶ 20:54 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT Disclosure
Taylor: Sierra reached $100M ARR in seven quarters, now around $165M
“We reached a hundred million dollars in ARR in seven quarters, a 150 in eight quarters. We're, I think, around one 65 now, one month into our you know, next quarter or so.”
Bret Taylor Mar 10, 2026 ▶ 21:11 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT Assertion Supported
Taylor: Ramp automates 90% of its customer support cases using Sierra
“Well, they're automating 90% of their cases.”
Bret Taylor Mar 10, 2026 ▶ 32:20 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Taylor: Grounding AI agents is harder for famous brands than obscure ones
“It's actually easier when the internet has never heard of you and you want to make a well-grounded agent, it's actually pretty easy because there's no temptation from the LLMs to go off script. So actually, I would say. Ironically, the harder challenge is when…”
Bret Taylor Mar 10, 2026 ▶ 43:09 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT Prediction Not checkable as stated
Taylor: Specialized Cantonese voice AI will be fully commoditized within three years
“So we did all this work, and in fact, you know, we, I think, have the best Cantonese support on the market. Great for us, and it's a huge selling point, and it's a technology that will certainly be commodity, commoditized in three years.”
Bret Taylor Mar 10, 2026 ▶ 47:18 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT Disclosure
Taylor: Sierra uses outcome-based pricing, charging only for fully resolved cases
“So, we do outcomes-based pricing. So, for a customer service context, that means if the AI agent resolves the case, no human intervention there's a pre-negotiated sort of rate for that, and if we do have to escalate to a person, it's free. For sales, it would …”
Bret Taylor Mar 10, 2026 ▶ 1:01:41 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
NO PRIORS Opinion
Gil: Decagon and Sierra Represent a Shift Toward Utilization-Based Support Agents
“Ultimately, I think Decagon and Sierra are examples of companies where you're moving from proceed software to basically utilization based customer support related agents, right? That is a real shift. That may impact some of the prior wave of sort of perceived …”
Elad Gil Feb 19, 2026 ▶ 2:27 The AI Code Slop: Risk or Opportunity?
20VC 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
20VC 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
AI Startup Sierra’s True Competitive Moat Is Bret Taylor’s Sales Reach
“And I came up with the example of Sierra, which I think unique asset is Brett Taylor. I mean, they have full control of Brett, who's one of the best salespeople, chairman of OpenAI. He can make a call to any company, any country, and they'll take his call. You…”
Gokul Rajaram Jan 29, 2026 ▶ 22:57 He Built The Revenue Engines for Google, Facebook & Square · Invest Like The Best
BIG TECHNOLOGY Prediction Open · timeframe Jan 2031
Bret Taylor: AI Agents Will Shift Software Toward Outcomes-Based Pricing
“I would argue that actually, I think agents will go the way of outcomes based pricing where, you know, for example, at CIRA, we charge per resolved case for our customer service agents. I think if you made an agent to Audit your financials. You should pay per …”
Bret Taylor Jan 28, 2026 ▶ 12:51 Is AI Killing Software? — With Bret Taylor, OpenAI's board chair and CEO of Sierra
BIG TECHNOLOGY Prediction Not checkable as stated
Taylor: AI agents will handle most customer interactions instead of websites
“Your AI agent is going to be your digital front door, and most of your customer interactions will happen via your AI agent, not by, from your mobile app or your website, even if they exist in those platforms,”
Bret Taylor Jan 28, 2026 ▶ 23:13 Is AI Killing Software? — With Bret Taylor, OpenAI's board chair and CEO of Sierra

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