Enterprise Sales Director - Strategic, Healthcare

Sierra

1d•CA$375,000 - CA$430,000•Onsite

About The Position

Sierra is building a platform to help businesses create better, more human customer experiences with AI. The company is primarily in-person in San Francisco, with expanding offices globally. Sierra is guided by core values: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. The co-founders are Bret Taylor and Clay Bavor, both with extensive backgrounds in tech leadership. The Healthcare team at Sierra partners with leading health plans, providers, and platforms to deliver AI agents that handle sensitive conversations, transforming patient and policyholder interactions with the healthcare system. The goal is to make care more accessible, human, and affordable.

Requirements

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.

Nice To Haves

Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders.
Experience operating alongside founders/executives in front of strategic customers.

Responsibilities

Architect Sierra's most complex deals, leading large multi-BU, multi-geo opportunities with sophisticated deal structures and risk management.
Operate as part of the customer's team, building trusted relationships across the customer C-suite and working teams.
Engage at the founder level, managing Sierra's co-founders in customer interactions.
Bring precision to messaging, positioning, and timing in all interactions.
Shape strategy for approaching important accounts and set standards for the broader sales organization.
Operate as an AI-native seller, leveraging AI tools across the sales cycle for research, outreach, summarization, forecasting, and execution, while adopting new tools to improve efficiency.