Based in San Francisco, Sierra is building a platform to help businesses deliver AI-driven, human-centered customer experiences. We are primarily an in-person company with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. Remote work is available (Remote OK). Role: Enterprise Sales Director – Strategic, Healthcare. What you'll do: Architect Sierra's most complex deals by leading our largest multi-business-unit, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision. Operate as part of the customer's team with trusted relationships across C-suite and cross-functional teams. Regularly engage with Sierra's co-founders in front of customers, delivering pitches with founder-level conviction and expertise. Bring precision to messaging, positioning, and timing across every interaction. Shape strategy by influencing how Sierra approaches its most important accounts and setting the standard for the broader sales organization. Operate as an AI-native seller, leveraging AI tools across the full sales cycle—from account research to personalized outreach, call summarization, pipeline forecasting, and deal execution—to automate low-value tasks and reinvest time into high-value relationships, while continuously adopting new tools to work faster and smarter than traditional methods allow. What you'll bring: 10–12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts. Demonstrated success closing multi-million-dollar, multi-stakeholder deals across business uni

Based in San Francisco, Sierra is building a platform to help businesses deliver AI-driven, human-centered customer experiences. We are primarily an in-person company with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. Remote work is available (Remote OK). Role: Enterprise Sales Director – Strategic, Healthcare. What you'll do: Architect Sierra's most complex deals by leading our largest multi-business-unit, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision. Operate as part of the customer's team with trusted relationships across C-suite and cross-functional teams. Regularly engage with Sierra's co-founders in front of customers, delivering pitches with founder-level conviction and expertise. Bring precision to messaging, positioning, and timing across every interaction. Shape strategy by influencing how Sierra approaches its most important accounts and setting the standard for the broader sales organization. Operate as an AI-native seller, leveraging AI tools across the full sales cycle—from account research to personalized outreach, call summarization, pipeline forecasting, and deal execution—to automate low-value tasks and reinvest time into high-value relationships, while continuously adopting new tools to work faster and smarter than traditional methods allow. What you'll bring: 10–12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts. Demonstrated success closing multi-million-dollar, multi-stakeholder deals across business uni