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Sierra Buys AI Agent Startup Takeoff to Expand Into Long-Horizon Autonomous Tasks After Revenue Hits Nearly $10 Million

businessmergers-acquisitionsaiai-productsai-agents-codingai-enterprise-tools 2 posts · 2 accounts

Sierra acquired Takeoff, an artificial intelligence agent startup focused on long-horizon autonomous workflows, expanding beyond its established customer support software. The transaction follows the startup's rapid commercialization, as revenue scaled from zero to nearly $10 million across multiple seven-figure contracts within a year.

The acquisition shifts Sierra's operations toward autonomous tasks capable of running for hours or days, leveraging the company's existing revenue-driven agent platform. Sierra's leadership outlined a strategy backing fully autonomous agents that perform human-level work at software scale, betting that future enterprise AI businesses will be built around measurable outcomes rather than inference volume.

From the sources (2 posts)

@steph_palazzolo

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 da

@btaylor

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 somet

Preview built on a synthetic news corpus (16 weeks, Apr–Jul 2026). Impact calls are model reads, not price data.

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