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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 prospecting and relationship management for Sierra's largest enterprise customers. Your responsibilities include identifying and targeting potential customers through research, networking, and strategic outreach; building and maintaining relationships with key decision-makers; negotiating and closing complex 6- and 7-figure ACV deals; developing and executing sales strategies to meet revenue targets; and collaborating cross-functionally with GTM, product, technical, and operations teams.
You will operate as an AI-native seller, leveraging AI tools throughout the sales cycle—from account research and personalized outreach to call summarization, pipeline forecasting, and deal execution—to automate low-value tasks and focus on high-value customer relationships.
Required qualifications: 6–8 years in enterprise customer-facing sales roles closing large accounts; experience managing $1M+ quotas and running end-to-end complex deals; exceptional verbal and written communication skills; analytical mindset with ability to identify market opportunities and make data-driven decisions; proven track record in prospecting and lead generation.
Preferred: familiarity with the AI landscape, key players, and emerging trends.
Sierra offers unlimited PTO, medical/dental/vision benefits, life and disability insurance, retirement plans, parental leave, fertility benefits, discretionary stipends, and equity participation for full-time employees.
