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Enterprise Sales Leader, Healthcare

SierraUS - RemoteSales
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Salary
$450K - $470K USD
Job type
Full-time
Work mode
Remote
Posted
10 Jul 2026
Status
Open · checked 7d ago

About this role

Role Overview

Sierra is seeking an Enterprise Sales Leader for their Healthcare team to oversee regional sales performance and guide a growing group of professionals in a remote capacity. This position suits an experienced sales leader with a background in complex enterprise deal-making and team management.

Key Responsibilities

Build, onboard, and mentor a high-performing regional sales team while fostering an environment of accountability and collaboration.
Take ownership of regional sales targets, forecast precision, and pipeline quality alongside RevOps.
Participate directly in customer and prospect interactions to assist with complex buying committees, negotiations, and closing strategies.

Requirements

Possess 10 to 15 or more years of experience in enterprise customer-facing sales roles focusing on large accounts.
Bring at least 5 years of experience in managing, coaching, and developing high-performing enterprise sales teams.
Demonstrate a strong track record of running end-to-end complex deals valued at $1 million or more.
Maintain exceptional verbal and written communication abilities alongside a data-driven, analytical mindset.

Nice to Have

Familiarity with the artificial intelligence landscape, key industry players, trends, and AI tooling workflows.
Experience in establishing go-to-market strategies and building sales motions or teams from an early growth stage.

Skills and Tools

Enterprise sales leadership
Pipeline management and forecasting
Complex deal negotiation
Sales strategy execution

Salary and Benefits

Annual salary ranging from $450,000 to $470,000 USD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision insurance for employees and their families.
Life insurance, disability benefits, and retirement plan options.
Parental leave, plus fertility and family building benefits via Carrot.
Discretionary benefit stipend and free alphorn lessons.

About the Company

Sierra serves as a leading platform for customer-facing artificial intelligence agents, partnering with major global brands to transform customer service and business growth. The organization is guided by core values emphasizing trust, customer obsession, craftsmanship, intensity, and family support.

How to Apply

Interested candidates should visit the official Sierra careers page to submit an application for this remote position.

Questions candidates ask

What is the salary for the Enterprise Sales Leader, Healthcare role?

The annual salary for this position is between $450,000 and $470,000 USD.

Is this position remote?

Yes, this role is listed as US - Remote.

What level of experience is required for this sales leadership position?

Applicants need 10 to 15+ years of enterprise customer-facing sales experience, including at least 5 years of people management experience leading enterprise sales teams.

What type of deals will this sales leader manage?

The role involves managing end-to-end complex enterprise deals valued at $1 million or more.

What benefits are provided to full-time employees?

Full-time employees receive flexible paid time off, medical, dental, vision, life and disability insurance, parental leave, family building benefits through Carrot, a discretionary stipend, and retirement plans.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site