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Sierra is building an AI platform that helps businesses create better, more human customer experiences. The company is headquartered in San Francisco with offices across major US and international cities, 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 and AR/VR initiatives).
As Enterprise Sales Director for the Retail vertical, you will lead Sierra's most complex, strategic deals with the world's largest retailers. The retail team focuses on AI agents that power customer service, product discovery, personalized recommendations, cart recovery, and in-store support—driving both cost savings and revenue generation for major apparel, beauty, grocery, big-box, and marketplace brands.
Your responsibilities include architecting multi-business-unit, multi-geography deals with sophisticated structures; building and maintaining trusted relationships across customer C-suites; regularly engaging Sierra's co-founders in customer conversations; and setting the standard for precision in messaging, positioning, and deal execution. You will operate as an AI-native seller, leveraging AI tools across the full sales cycle—from account research and personalized outreach to call summarization and pipeline forecasting—to focus your time on high-value customer relationships.
You bring 10–12+ years of enterprise sales experience managing the largest, most complex accounts. You have a proven track record closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies, with experience running $1M+ quotas and closing 6- and 7-figure ACV deals. You possess deep C-suite relationships, exceptional executive communication skills, mastery of complex deal structuring and risk navigation, and a reputation for precision and trust. Ideally, you have familiarity with the AI landscape, can speak credibly to both technical and business stakeholders, and have experience operating alongside founders and executives in front of strategic customers.
