Enterprise Sales Leader, Healthcare

About us: Sierra is building a platform to enable every company to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. Our co-founders are Bret Taylor and Clay Bavor.

About the Healthcare team: Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle sensitive and high-stakes conversations. Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.

What you'll do: Lead and develop a high-performing sales team: hire, onboard, and develop AEs; coach reps on deal strategy, pipeline management, and execution; create a culture of accountability, learning, and collaboration. Own regional performance: own your regional number and forecast accuracy, inspect pipeline quality, and drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights. Be deeply involved in deals: join key customer and prospect conversations, help reps navigate complex buying committees and late-stage deals, support pricing, negotiation, and close strategy.

What you'll bring: 10-15+ years of experience in enterprise customer-facing sales, identifying and closing large accounts. 5+ years managing, mentoring, and developing a high-performing enterprise sales team. Experience running and managing end-to-end complex deals ($1M+). Strong communication skills and analytical mindset.

Even better: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows. Experience building GTM strategies and sales teams from scratch or early-stage growth.

What we offer: Flexible (unlimited) paid time off, medical, dental, and vision benefits, life insurance and disability benefits, retirement plan, parental leave, fertility and family building benefits, lunch and snacks, discretionary benefit stipend, and free alphorn lessons.