Enterprise Sales Director, Healthcare

Sierra

1d•CA$305,000 - CA$370,000•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 values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family. The co-founders are Bret Taylor and Clay Bavor, both with extensive backgrounds in technology and AI. The Healthcare team at Sierra partners with leading health plans, providers, and healthcare platforms to deliver AI agents that handle sensitive conversations, transforming how patients and policyholders interact with the healthcare system. Customers include major health insurance networks, nonprofit providers, multi-site practices, diagnostics companies, and financial platforms. The role offers an opportunity to transform the patient experience and make care more accessible, human, and affordable.

Requirements

6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Exceptional verbal and written communication abilities.
Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

Nice To Haves

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

Responsibilities

Identify and target potential customers through research, networking, and cold calling to build new relationships and drive revenue, pipeline, and deployment capacity.
Build and maintain strong relationships with key decision-makers and stakeholders at the largest customers, serving as their primary point of contact and exceeding expectations.
Lead negotiations with existing and prospective customers, addressing objections, closing deals, and navigating contracts and agreements with legal and finance stakeholders.
Develop and execute sales strategies to meet or exceed sales targets, crafting tailored presentations and proposals, and collaborating with marketing on sales campaigns.
Work closely with the broader Go-To-Market team, as well as product, technical, and operations organizations to deliver the industry-leading product.
Leverage AI tools across the full sales cycle, including account research, personalized outreach, call summarization, pipeline forecasting, and deal execution, to automate tasks and focus on high-value customer relationships.