Sierra, every mention
47 scenes (2025), the whole family · ← back to Sierra
tap a year for its mentions
every year 2025 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
Matt Fitzpatrick: Who Wins the Data Labelling Race & Why Al Needs Forward-Deployed Engineers · 20VC with Harry Stebbings
- ▶ 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
- ▶ 14:54 Harry Stebbings Manus, Sierra, Firework, Legora, Cerebris, Langchain.
a16z's David George on the Most Controversial Bet at a16z & Do Margins and Revenue Matter in AI? · 20VC with Harry Stebbings
- ▶ 39:42 Harry Stebbings And, like, Brett and Sierra is obviously, like, you know, the OG of OGs of SaaS.
- ▶ 41:58 Harry Stebbings You know, ten billion for Sierra is, is, is amazing.
SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
- ▶ 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
- ▶ 35:34 Harry Stebbings Sierra, Brett Taylor, formerly co-CEO of Salesforce, 7 times in the scene
- ▶ 51:22 Jason Lemkin And to get this fin level of experience or better or Decagon or Sierra, you got to train the thing for a month or three weeks with FDs and the rest.
- ▶ 54:20 Harry Stebbings One that's really tied to this, like Sierra hit revenue milestone, does it justify price?
- ▶ 57:19 Jason Lemkin You're not being judged as Sierra.
Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 5:29 Harry Stebbings Sierra with Brett Taylor over a hundred million in ARR.
Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 20VC with Harry Stebbings
Robinhood Founder & CEO, Vlad Tenev: Robinhood’s $85BN Resurgence & Tokenizing SpaceX & OpenAI · 20VC with Harry Stebbings
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 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
- ▶ 1:06:38 Harry Stebbings Sierra's a special company.
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
- ▶ 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.