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Sierra is building an AI platform that helps businesses create better, more human customer experiences. The company is 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).
The Retail team partners with major retailers across apparel, beauty, grocery, big-box, home, auto, and consumer services. Sierra's AI agents serve millions of shoppers daily—handling order tracking, returns, product discovery, and customer service. Uniquely, the platform generates revenue beyond cost savings through personalized recommendations, cart recovery, win-back campaigns, and in-store support.
As Enterprise Sales Director for Retail, you will lead prospecting and relationship management with large retail customers, managing complex 6- and 7-figure ACV deals. You'll identify and target enterprise prospects through research and networking, serve as primary contact for key decision-makers, negotiate and close deals, and develop tailored sales strategies. You'll collaborate cross-functionally with GTM, product, technical, and operations teams. The role emphasizes operating as an AI-native seller—using AI tools for account research, personalized outreach, call summarization, and pipeline forecasting to focus on high-value customer relationships.
You bring 6–8 years of enterprise sales experience, a proven track record managing $1M+ quotas, and expertise closing large accounts. Strong communication, analytical thinking, and prospecting skills are essential. Familiarity with the AI landscape is a plus.
Sierra is primarily in-person in San Francisco with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. The company is guided by values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family.
