AI customer support company with a reported $15.8B valuation.
- Seinfeld
- The Feds and 20+ States Sue Amazon for Manipulating Ad Auctions
- Amid Personal Assistant Investor Frenzy, Town Nears $1 Billion Valuation in Round Led by Instinct-Backer Index Ven…
- OpenAI’s Head of Design_ This is the best time in history to be a designer _ Ian Silber
- Decagon Hit $100 Million Betting Against Forward Deployed Engineers
- 💥Personal AI Operating Stack, What Got Hyped vs What Got Built, How VCs Decide & More
- Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486]
- Chasing Trillion-Dollar Companies, Founder Ambition, Token Budgets, and Regulatory Capture with Sarah & Elad
- Decagon’s Playbook for Building Enterprise AI Applications
- EU Regulators Fine Google $1B
- 🚀 Prometheus rising
- 💥Fund Performance Benchmarks, How Agent Loops Work, Portfolio Construction, Enterprise Software Playbook & More
“Its new Personas product lifted a telecom's problem-resolution rate 'by nearly 50%'”
Source→“it powers OpenAI, Anthropic, Cursor, Replit, Sierra, Clay... essentially Stripe for enterprise features”
Source→“Noah Sheehan... Founder of Instinct, born 2003, formerly an engineer at Sierra”
Source→“How that is going to make your job different than working at Anthropic or at OpenAI or at Eleven Labs or at Sierra...”
Source→“Multimodal Agents by Sierra — AI agents that switch between voice, text, and visuals (93 votes)”
Source→“I think everyone in this category is being forced to [expand] by Brett Taylor, who's being very clear in terms of his expansion.”
Source→“The winner in the existing world is only worth 50 [billion]. So as you get these bigger market caps like Sierra, you have to go beyond service cloud replacement to be a big company... you have to sell the whole operating system.”
Source→“Every startup that I'm an investor in that starts to expand upmarket ends up working with WorkOS. And that's because they are the best”
Source→“joining startups such as Sierra and Fin in experimenting with outcome-based pricing as software vendors rethink fixed subscriptions and usage fees”
Source→“Sierra comes in and they say, well, we will resolve those tickets for a fifth of the price... effectively the AI is running the entire workflow end-to-end.”
Source→“What do OpenAI, Anthropic, Cursor, Replit, Sierra, Clay, and hundreds of other winning companies all have in common? They are all powered by WorkOS.”
Source→“Sierra is an 800-pound gorilla that has three times the funding...and has well-surpassed $200 million in annualized revenue”
Source→“Legora, Sierra, and Ramp saw theirs accelerate starting January 2026, driven partly by sustained growth and a more favorable fundraising market.”
Source→“The 100x ARR Multiple Is Back: The article notes a 2021 piece on the '100x ARR multiple' as a historical premium; five years later, multiples are back at similar levels, but reported growth rates underneath are running roughly 3x faster... Legora, Sierra, and Ramp saw theirs accelerate starting January 2026, driven partly by sustained growth and a more favorable fundraising market.”
Source→“We used to be building castles. Now we're building sandcastles that get washed away. And if you don't think about software that way... You're just not going to make it... It's what Brett Taylor calls like sandcastles.”
Source→“They're technologists, but they actually have lived in enterprise world for a long time... And now we have these long-running agents with Horizon that can do more and more stuff.”
Source→“Bret Taylor - Valley-famous CEO of Sierra; former co-CEO of Salesforce and chairman of Twitter's board”
Source→“Sierra is an 800-pound gorilla that has three times the funding...and has well-surpassed $200 million in annualized revenue”
Source→“Sierra has built customer-facing AI agents that can do a huge range of things. Not just basic support stuff like answering questions, but the kind of hard things that are closer to a company's core value creation.”
Source→“Literally every startup that I'm an investor in that starts to expand upmarket ends up working with WorkOS. And that's because they are the best.”
Source→“If you look at the markets that Harvey or Open Evidence or Decagon or any of these folks at Sierra entered, you know, four or five years ago, three or four years ago... it was big, big markets that could be in the roadmaps of these labs.”
Source→“Within basically a month, they spun up like seven new journeys on Decagon. And it'd taken a year to get three. So it's just kind of the speed of iteration.”
Source→“Literally every startup that I'm an investor in that starts to expand upmarket ends up working with WorkOS.”
Source→“Sierra, which builds AI customer-service agents for businesses, acquired one-year-old San Francisco startup Takeoff, whose autonomous agents complete multi-step jobs across phone, text, email, and software systems over days or weeks.”
Source→“We actually just became, as of the close last week on Tuesday, one of the fastest enterprise company with a direct sales motion to go from one to 150, beating Sierra with one quarter.”
Source→“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... 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.”
Source→“We have not yet appreciated the unbounded demand for, call it frontier levels of intelligence... I think it's hard to get your mind around when you have intelligence that can work around the clock to invent, to build, to discover how you would use that and how much of it you could use.”
Source→“I have heard and I have observed that top engineers who are really leaning in to Claude Code, Codex, and so on, are spending more than $100,000 on a run rate basis on tokens per year... I would not bet on 3.8%. I would bet on much closer to 20%.”
Source→“We recently acquired a company in Japan, Opera Technologies... to hit the ground running there and to have a team that can be attuned to the cultural nuances of Japan.”
Source→“Benchmark portfolio company; highlighted for outcome-based pricing on completed customer support deflections — a model where the monetized unit is inference”
“Sierra is outcome-based AI customer support platform; charges per completed deflection of a customer query. Described as the 'horizontal AI winner' in Benchmark's portfolio.”
Source→“What do OpenAI, Anthropic, Cursor, Vercel, Replit, Sierra, Clay, and hundreds of other winning companies all have in common? They are all powered by WorkOS.”
Source→“WorkOS... 'Literally every startup that I'm an investor in that starts to expand upmarket ends up working with WorkOS... It's essentially Stripe for enterprise features.'”
Source→“Utility software company Kraken Technologies says it will use AI startup Sierra's customer service tech to serve millions of customers.”
Source→“Cursor, Clay, Harvey, Cognition, Sierra, Baseten, Fireworks, and Lovable all went from roughly $0 to $100M ARR in the past two years, compressing what used to be a 6-10 year journey.”
Source→“We really were watching Brett Taylor at Sierra... He's building this fantastic company called Sierra. We're not involved. But that's where the rubber hits the road.”
Source→“Literally every startup that I'm an investor in that starts to expand upmarket ends up working with WorkOS. And that's because they are the best.”
Source→“What do OpenAI, Anthropic, Cursor, Vercel, Replit, Sierra, Clay, and hundreds of other winning companies all have in common? They are all powered by WorkOS.”
Source→“Customer support saw the steepest decline of any GTM role, down 37%, reflecting traction from AI support products like Sierra ($15.8B) and Decagon ($4.5B).”
“Sierra charges purely based on outcomes. If the AI resolves the customer service issue without transferring to a human agent, they charge. If it transfers, they don't charge... As a customer, I'm completely interest-aligned with Sierra — we both want to solve the problem, and we both want to minimize token burn.”
Source→“His AI software startup Sierra has built a promising business selling AI solutions for customer service uses.”
Source→“He was calm, confident, and well informed. He parried Musk's lawyers' questions about Altman's firing and why he chose to join the board... Taylor's name has been casually bandied about as a potential OpenAI CEO, but this was the first time it seemed real.”
Source→“Taylor…has said that the best-case outcome for agentic AI is lower costs and higher revenue for clients, but before those returns materialize, the ramp-up phase can be pricey.”
Source→“The company says it started with just four design partners a couple of years ago. Today it claims to have more than 40% of the Fortune 50 as customers, and says the agents running on its platform are handling billions of interactions.”
Source→“Sierra went from four design partners to 'more than 40% of the Fortune 50 as customers' and grew ARR from $100M in November to $150M by February”
Source→AI-extracted from podcast / newsletter / paper summaries. May contain errors.