Sierra is already one of the most significant enterprise software companies of the past two years. Founded in 2023 by Bret Taylor, the former co-CEO of Salesforce and current chairman of OpenAI's board, and Clay Bavor, a longtime Google executive, the company builds AI agents for large businesses. It crossed $150 million in annual revenue within eight quarters of launching, a pace its own founders described as faster than expected. Its customers include Cigna, Nordstrom, Rocket Mortgage, and SiriusXM, and it now serves roughly 40% of the Fortune 50.
Sierra's agents today handle customer service: answering questions, processing returns, managing subscriptions, and routing calls. These are short, contained interactions. What Takeoff built is different. Takeoff's technology lets an AI agent handle a job that unfolds over days or weeks, across phone, email, SMS, and web portals, making dozens of decisions along the way without a human steering it at each step. Think of the difference between a bank teller answering one question versus a loan officer walking a borrower through the entire mortgage process, start to finish.
Takeoff was founded in 2025 and raised $15 million from investors Matrix and Lachy Groom. By mid-2026, the three-person company had secured several seven-figure contracts across lending, healthcare, telecom, media, and travel. Its founder, Aakash Thumaty, built the business on a clear thesis: the underlying AI models are becoming a commodity, and the real business advantage goes to whoever can deliver measurable, industry-specific outcomes. Sierra's founders agreed with that view completely, and that alignment drove the deal.
The combined technology will become a new platform called Horizon. Sierra's existing setup handles conversational, short-turn interactions well. Horizon is designed to go further: running outbound and inbound interactions over days or weeks, maintaining context across every touchpoint, and completing tasks that previously required a person to follow through. The early use cases are concentrated in industries where a single customer journey involves many steps spread over time: mortgage origination, insurance claims, healthcare referrals, and telecom onboarding.
This deal fits a larger pattern. Enterprise AI in 2026 is consolidating fast. OpenAI completed six acquisitions in the first quarter of 2026 alone. Larger platform companies are buying niche specialists rather than building from scratch, because the specialists already have working technology and paying customers. Takeoff had both, which is why Sierra moved when it did.
For operators in traditional industries, the practical implication is straightforward. The tools that can handle a complete multi-step workflow, without human handoffs at every stage, are arriving faster than most organizations expected. Industries with long customer journeys and high process costs, including insurance, healthcare, financial services, retail, and logistics, are the first targets. The question is not whether this technology will reach your industry. The question is whether you start understanding it now, while there is still time to shape how it gets deployed in your organization, or later, when the decisions have already been made for you.
No financial terms for the acquisition were disclosed. Takeoff's existing customers will continue to be served through Sierra's platform.