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Sierra is building an AI agent platform that enables companies to deliver better, more human customer experiences. The company partners with industry leaders including SoftBank, Uber, Rivian, CLEAR, and Sutter Health. Founded by Bret Taylor (former Salesforce co-CEO, Facebook CTO, Google Maps co-creator) and Clay Bavor (18-year Google veteran who led Google Labs, AR/VR, and Google Workspace), Sierra is headquartered in San Francisco with growing offices across North America, Europe, and Asia.
The Enterprise Sales Director role leads Sierra's Consumer Business Insights vertical, which spans CPG, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, energy, utilities, and related sectors. You will architect Sierra's most complex, multi-business-unit, multi-geography deals with some of the world's largest and most established companies.
Key responsibilities include: leading sophisticated deal structures and managing risk with precision; building and maintaining trusted relationships across customer C-suites and working teams; regularly engaging Sierra's co-founders in front of strategic customers; operating with exacting craft in messaging, positioning, and timing; influencing how Sierra approaches its most important accounts; and leveraging AI tools across the full sales cycle—from account research and personalized outreach to call summarization, pipeline forecasting, and deal execution.
You will bring 10-12+ years of enterprise/strategic sales experience owning the largest and most complex accounts, with demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies. You must have experience managing $1M+ quotas and running end-to-end complex 6- and 7-figure ACV deals, deep C-suite relationships, mastery of complex deal structuring and risk navigation, and exceptional executive communication skills. Familiarity with the AI landscape and experience operating alongside founders/executives in front of strategic customers are highly valued.
Sierra's culture is built on five core values: Trust (accountability, empathy, quality, responsiveness), Customer Obsession (deeply understanding customer business goals and relentlessly driving outcomes), Craftsmanship (getting details right, continuous self-improvement), Intensity (playing to win, fixing what isn't best), and Family (balancing intensity with support and respect). The company offers flexible unlimited PTO, medical/dental/vision coverage, and is recognized as a top technology company for parents.
