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Sierra is building an AI platform to help businesses create better, more human customer experiences. The company was 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 offices across Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.
As Enterprise Sales Director, you will lead Sierra's most complex, strategic deals—multi-business unit, multi-geography opportunities requiring sophisticated deal structuring and risk management. You'll operate as a trusted advisor to customer C-suites, regularly engaging Sierra's co-founders in front of strategic accounts. Your role is to architect high-value deals, build peer-level relationships with executive buyers, and shape how Sierra approaches its most important accounts.
Key responsibilities include: architecting complex multi-stakeholder deals; managing C-suite relationships with executive gravitas; engaging co-founders strategically with customers; operating with precision in messaging and positioning; influencing Sierra's enterprise sales strategy; and leveraging AI tools across the full sales cycle (account research, outreach, call summarization, forecasting, deal execution) to focus on high-value customer relationships.
You'll bring 10-12+ years of enterprise sales experience managing the largest, most complex accounts. You must have a track record closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies, with demonstrated success managing $1M+ quotas and closing 6- and 7-figure ACV deals. Deep C-suite relationships, mastery of complex deal structuring, and exceptional executive communication are essential. Ideally, you have familiarity with the AI landscape and experience operating alongside founders/executives in front of strategic customers.
Sierra's culture is built on five core values: Trust (accountability, empathy, quality, responsiveness), Customer Obsession (deeply understanding customer goals and driving outcomes), Craftsmanship (attention to detail and continuous improvement), Intensity (playing to win, fixing problems openly), and Family (balancing intensity with support for personal and professional well-being).
