Sales Director - Healthcare

Sierra

3d•$300,000 - $345,000•Onsite

About The Position

Sierra is building a platform to help businesses create better, more human customer experiences using 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, Bret Taylor and Clay Bavor, have extensive experience in technology leadership roles at major companies like Salesforce, Facebook, and Google. The Healthcare team is a rapidly growing sector for Sierra, with agents reaching over 50% of U.S. families. They partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle sensitive conversations, assisting members with benefits understanding and billing inquiries. Their healthcare customers include major health insurance networks, nonprofit providers, multi-site practices, diagnostics companies, and financial platforms. Sierra aims to transform the patient experience, making care more accessible, human, and affordable through conversational AI.

Requirements

8-12+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Experience managing a $1M+ quota.
Experience running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: 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.
Experience building Go-To-Market strategies.
Experience building sales teams and sales motions from scratch, or from early stage growth.

Responsibilities

Identify and target potential customers through research, networking, and cold calling.
Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Build and maintain strong relationships with key decision-makers and stakeholders at the largest customers.
Serve as the primary point of contact for customers and exceed their expectations.
Lead negotiations with existing and prospective customers, addressing objections and closing deals.
Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Develop and execute sales strategies to meet or exceed sales targets.
Craft tailored sales presentations and proposals that meet enterprise customer needs.
Collaborate with the marketing team to implement effective sales campaigns and presentations.
Help define the sales motion and impact how the Go-To-Market function operates and succeeds.
Work closely with the broader Go-To-Market team, as well as product, technical, and operations organizations to deliver the product.