Enterprise Sales Director - Majors, Healthcare

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. 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.

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 some of the most sensitive and high stakes conversations in any industry. Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.

• Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
• Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
• Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
• Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
• Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
• Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
• Operate as an AI-native seller: 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 that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

• 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• Proven ability to multi-thread and build trusted relationships across customer C-suites.
• Exceptional verbal and written communication.
• Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.

• Familiarity with the AI landscape, key players, and emerging trends.

We want our benefits to reflect our values and offer the following to full-time employees:

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability benefits
• Retirement plan dependent on country of employment
• Parental leave
• Fertility and family building benefits through Carrot
• Lunch, as well as delicious snacks and coffee to keep you energized
• Discretionary benefit stipend giving people the ability to spend where it matters most
• Free alphorn lessons

Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.