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Sierra is building an AI platform that helps businesses deliver better, more human customer experiences. The healthcare team has already reached over 50% of U.S. families through AI agents deployed with leading health plans, providers, and healthcare platforms. These agents handle sensitive conversations—from benefits education to billing resolution—transforming how patients interact with the healthcare system.
As Enterprise Sales Director for Healthcare, you'll lead the sales strategy and execution for this high-impact vertical. Your responsibilities include prospecting and identifying enterprise customers (health plans, providers, diagnostics companies, financial platforms), building and maintaining relationships with key decision-makers, negotiating and closing complex 6-7 figure ACV deals, and developing tailored sales strategies to exceed targets. You'll collaborate cross-functionally with GTM, product, technical, and operations teams to drive deployment and revenue.
You'll operate as an AI-native seller, leveraging AI tools throughout the sales cycle—account research, personalized outreach, call summarization, pipeline forecasting—to automate low-value work and focus on high-value customer relationships. The role requires managing a $1M+ quota and running end-to-end enterprise deal cycles.
You bring 6-8 years of enterprise customer-facing sales experience with a proven track record closing large accounts. You have strong communication skills, an analytical mindset, and expertise in prospecting and lead generation. Familiarity with the AI landscape and healthcare industry is a plus. Sierra is headquartered in San Francisco with offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. The company was founded by Bret Taylor (former Salesforce co-CEO, OpenAI Board Chair) and Clay Bavor (18-year Google veteran, led Google Labs and AR/VR initiatives).
