Sierra

Self-driving money with @zachperret, @claybavor and @Kr00ney cnbc.com/video/2026/08/…

Financial services used to move like this: branch > website > app. Now it's just a conversation, with one agent 💬 Plaid Link inside @SierraPlatform pulls your bank data mid-chat to keep loans, payments, and claims moving. More here: pla.id/sierra

Last month we introduced Horizon, which enables agents to pursue long-term goals like originating a loan or settling an insurance claim. Today, we're excited to announced our partnership with @Plaid so customers can now securely connect their bank accounts with agents built on Sierra. This not only enables people to make payments or verify their finances without leaving the conversation — the agent can then use that information to complete longer-running tasks like refinancing a loan. It's a big pivot beyond customer support, to agents that can drive revenue, proactively engaging over days, weeks or months to deliver meaningful business outcomes. Read more from me and @ Will Robinson below. sierra.ai/blog/our-partn…

Cost saving agents vs revenue agents your CEO is buying.

StoreEase built an AI agent to answer self-storage customers 24/7, on any channel. Now, after-hours calls that used to go to voicemail convert directly into revenue — and customer reviews haven't dipped. sierra.ai/customers/stor…

Human in the loop vs truly autonomous agents @letsleverup with @tbpn

LINE MAN Wongnai connects 10M+ users, 500K+ merchants, and 250K+ riders in Thailand. Now they're building AI agents for all three with Sierra: sierra.ai/customers/line…

Oh but it was so much fun ...

Thrilled to share that Takeoff has been acquired by Sierra. Last December, Aakash pitched Takeoff to me before I knew what a ‘long horizon’ agent meant. I couldn’t say I expected the countless all-nighters, maximum customer stress, and multimillion dollar deals that came with it. But we figured it out. We've proven that agents can take on real jobs autonomously: originating a loan, onboarding a patient, chasing down a prior authorization, and see them through across days and weeks instead of just a single conversation. I feel lucky to have been on this adventure with @letsleverup and @spenciefy and am energized to continue this work with @btaylor and the incredible team at Sierra!

Did you consider training your own models? @HarryStebbings

Pinecone makes it to 20VC and @HarryStebbings

The best part about this acquisition is I get to build agents with @letsleverup all day - he is truly one of a kind

Bret Taylor's Sierra is pushing beyond customer support with its acquisition of AI agent startup Takeoff. In this morning's AI Agenda, we get into how the deal will help Sierra break into longer-duration tasks that could run for hours or days. theinformation.com/newsletters/ai…

I’m incredibly excited to share that Sierra is acquiring TakeOff, the leader in long-horizon AI agents. @claybavor and I couldn't be more excited to welcome @letsleverup and the entire TakeOff team. In less than a year, they've built something truly special: an agent platform that delivers real business outcomes, is beloved by customers, and is growing incredibly quickly. Their maniacal focus on revenue driving, long-horizon agents has taken them from 0 to near 8 figures in revenue across several 7 figure contracts since the start of this year. As we got to know the team, it became clear we were making the same bet: that fully autonomous agents would perform human-level work at software scale and that the largest businesses in AI would be built around outcomes, not inference. Takeoff has built an exceptional platform and team to make that real, and together we’re excited to build the leading company in long-horizon AI agents. Welcome, Aakash and the Takeoff team. x.com/letsleverup/st…

In early 2024, I talked to a lot of experts and the consensus view was “you can reduce support costs by 30% with AI." We asked instead: "How can we create a level of service for small businesses that was impossible before?" Could we create an enterprise-level customer experience for a $50/mo freemium product? We're still building against this goal and @SierraPlatform has been an awesome partner. Thank you @btaylor and the entire team for the support from the beginning. A few learnings below 🧵

Read more here: sierra.ai/blog/building-…

Pinecone is our internal agent to make employees more effective. One of the biggest challenges in building Pinecone was making sure it had access to the right context. At Sierra, that context lives everywhere: Slack, GitHub, Salesforce, our data warehouse, production systems, internal docs, and dozens of other SaaS products. Just as we converged on a single agent in Pinecone, we wanted one “gateway” that safely connects AI agents to the tools and systems that power our company. It’s powered by Model Context Protocol (MCP), which has quickly become the standard way for exposing tools to AI agents. With MCP being “ancient” technology by AI industry standards (i.e older than a year), this should have been straightforward. In practice, it became one of those deceptively large engineering icebergs that we've learned to recognize at Sierra.

In a world where everyone has access to the same intelligence, how do companies differentiate themselves? The answer: their relationship with their customers. Long-horizon agents enable businesses to engage over weeks, months, or years. The agents learn and improve with every interaction. Over time, that's a deep competitive moat for the 40% of the Fortune 50 that work with Sierra. And it's knowledge and context that they own.