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Sierra is building an AI platform that helps businesses create better, more human customer experiences. The healthcare team has developed AI agents that already reach over 50% of U.S. families, partnering with leading health plans, providers, and healthcare platforms to handle sensitive conversations—from benefits education to billing resolution.
As Enterprise Sales Director for Healthcare, you will lead the sales strategy and execution for Sierra's healthcare business. You'll identify and target enterprise customers (health insurance networks, providers, urgent care practices, diagnostics companies, and healthcare financial platforms), build relationships with key decision-makers, and close complex 6- and 7-figure ACV deals. Your responsibilities include prospecting and lead generation through research and networking, managing relationships with the largest customers, negotiating and closing deals, developing tailored sales strategies and presentations, and collaborating cross-functionally with GTM, product, technical, and operations teams.
You'll operate as an AI-native seller, leveraging AI tools across the full sales cycle—account research, personalized outreach, call summarization, pipeline forecasting, and deal execution—to automate low-value tasks and focus on high-value customer relationships. The role requires managing a $1M+ quota and running end-to-end complex enterprise deals.
Sierra is founded by Bret Taylor (former Salesforce co-CEO, Google Maps co-creator, OpenAI Board Chair) and Clay Bavor (18 years at Google, led Google Labs and AR/VR initiatives). The company is primarily in-person in San Francisco with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. The culture is built on five core values: Trust, Customer Obsession, Craftsmanship, Intensity, and Family.
