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Enterprise Sales Director, Healthcare

SierraUS - RemoteSales
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Salary
$280K - $300K USD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 9d ago

About this role

This remote Enterprise Sales Director position at Sierra invites a seasoned sales professional to drive revenue within the healthcare sector, making it an ideal opportunity for candidates with extensive enterprise sales expertise. The role focuses on expanding the reach of advanced conversational artificial intelligence platforms across major health plans, providers, and healthcare networks.

Role Overview

The Enterprise Sales Director, Healthcare position involves leading complex sales cycles and building relationships with high-stakes healthcare clients. The professional in this role will introduce AI-driven solutions that assist patients and policyholders with sensitive conversations regarding benefits and billing. Candidates will operate as AI-native sellers, leveraging modern tools to streamline administrative tasks and dedicate more time to nurturing valuable client relationships.

Key Responsibilities

Identify and target potential enterprise clients through professional networking, thorough research, and cold calling.
Manage relationships with key decision-makers at major health insurance networks, nonprofit providers, and financial platforms.
Lead negotiations for six and seven-figure annual contract value deals, working alongside legal and finance teams.
Formulate targeted sales strategies, craft tailored proposals, and collaborate with marketing teams on impactful campaigns.
Partner cross-functionally with product, technical, and go-to-market organizations to ensure successful product deployment.

Requirements

Possess six to eight years of experience in an enterprise customer-facing sales capacity closing large accounts.
Demonstrated capability managing quotas exceeding one million dollars and executing end-to-end complex deals.
Exceptional verbal and written communication skills suitable for high-level stakeholder interaction.
Strong analytical mindset capable of interpreting market trends and making data-driven choices.
Proven history of proactive prospecting and lead generation within enterprise markets.

Nice to Have

Familiarity with the broader artificial intelligence landscape, key industry players, and emerging technology trends.

Skills and Tools

Enterprise prospecting and lead generation methodologies
Complex contract negotiation and deal closing
Market analysis and strategic sales planning
Cross-functional collaboration with technical and product teams
AI-powered sales tools for research, outreach, and pipeline forecasting

Salary and Benefits

Annual salary range between $280,000 and $300,000 USD
Flexible, unlimited paid time off policies
Comprehensive medical, dental, and vision coverage for employees and families
Life insurance, disability benefits, and retirement plans
Parental leave alongside fertility and family building assistance through Carrot
Discretionary benefit stipend and free alphorn lessons
Participation in company equity plans for eligible full-time employees

About the Company

Sierra builds customer-facing artificial intelligence platforms utilized by major global brands. Co-founded by industry veterans Bret Taylor and Clay Bavor, the organization is guided by core principles including trust, customer obsession, craftsmanship, intensity, and family support.

How to Apply

Interested applicants should visit the official Sierra careers page to submit their application.

Questions candidates ask

What is the salary range for the Enterprise Sales Director, Healthcare position?

The annual salary for this position ranges from $280,000 to $300,000 USD.

Is this job remote?

Yes, this is a remote position based in the United States.

How many years of experience are required for this role?

Applicants need 6 to 8 years of experience in an enterprise customer-facing sales role.

What types of healthcare organizations does Sierra partner with?

Sierra partners with major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.

What benefits are offered to full-time employees?

Full-time employees receive flexible paid time off, medical, dental, vision, life and disability insurance, retirement plans, parental leave, fertility benefits through Carrot, a discretionary benefit stipend, and equity plan participation.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site