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Sierra is building an AI platform that helps businesses deliver 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 operates primarily from San Francisco with offices across Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.
The Healthcare team at Sierra has built AI agents that reach over 50% of U.S. families, partnering with major health plans, providers, urgent care practices, diagnostics companies, and healthcare financial platforms. These agents handle sensitive, high-stakes conversations—from helping members understand benefits to resolving billing questions with empathy—transforming how patients interact with the healthcare system.
As Enterprise Sales Director for Healthcare, you will architect Sierra's most complex deals, leading large multi-business-unit, multi-geography opportunities with sophisticated deal structures and precision risk management. You'll operate as a trusted advisor to customer C-suites and working teams, regularly engaging Sierra's co-founders in front of strategic customers with founder-level conviction and expertise. You'll shape how Sierra approaches its most important accounts and set the standard for the broader sales organization.
You'll leverage AI tools across the full sales cycle—account research, personalized outreach, call summarization, pipeline forecasting, and deal execution—to automate low-value tasks and reinvest time into high-value customer relationships. This is a role for an AI-native seller who continuously adopts new tools to work faster and smarter than traditional methods allow.
You bring 10-12+ years of enterprise and strategic sales experience owning the largest, most complex accounts. You've closed multi-million-dollar, multi-stakeholder deals spanning business units and geographies, managed $1M+ quotas, and run end-to-end complex 6- and 7-figure ACV deals. You have deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers. You master complex deal structuring, risk navigation, and pricing, with exceptional executive communication and a reputation for precision and trust.
Ideal candidates have deep familiarity with the AI landscape and can speak credibly to both technical and business stakeholders, plus experience operating alongside founders and executives in front of strategic customers.
