Enterprise Sales Director - Strategic, Healthcare

About us

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.

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 a commitment to balancing Family along the way. 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 and Clay Bavor . 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

Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.

Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.

Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.

Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.

Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.

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.

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 spanning business units and geographies.

Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.

Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.

Mastery of complex deal structuring, risk navigation, and pricing.

Exceptional executive communication and a reputation for precision and trust.

Even better...

Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.