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Enterprise Sales Director - Majors, Healthcare

sierra · Canada - Remote · Full-time

About this role

ABOUT US

At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.

We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 

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 some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.

- Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.

- Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.

WHAT YOU'LL DO

- 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 be

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