Remote opportunity at
SierraEnterprise Sales Leader, Healthcare
Sierra is seeking an Enterprise Sales Leader, Healthcare to guide its sales operations and expand its footprint in the healthcare sector. Sierra operates a leading platform…
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About This Role
Sierra is seeking an Enterprise Sales Leader, Healthcare to guide its sales operations and expand its footprint in the healthcare sector. Sierra operates a leading platform for customer-facing artificial intelligence agents, serving prominent organizations like Sutter Health and major health insurance networks. The healthcare team's AI agents currently reach over half of U.S. families, handling high-stakes interactions such as benefits education and billing support. This full-time remote role offers a…
Job Description
Sierra is seeking an Enterprise Sales Leader, Healthcare to guide its sales operations and expand its footprint in the healthcare sector. Sierra operates a leading platform for customer-facing artificial intelligence agents, serving prominent organizations like Sutter Health and major health insurance networks. The healthcare team's AI agents currently reach over half of U.S. families, handling high-stakes interactions such as benefits education and billing support.
This full-time remote role offers a salary between USD 450,000 and 470,000 per year. The ideal candidate will take charge of regional performance, guide account executives, and actively participate in complex sales cycles with health plans, providers, and healthcare platforms. Sierra values trust, customer obsession, craftsmanship, intensity, and family balance, aiming to make patient care more accessible and affordable through advanced technology.
Responsibilities
- Hire, onboard, and develop account executives across the assigned region
- Coach sales representatives on execution, deal strategy, and pipeline management
- Manage regional performance metrics, sales forecasts, and pipeline quality
- Partner with Revenue Operations to maintain clean data and insights
- Participate directly in key customer and prospect meetings to help navigate complex buying committees
Requirements
- Possess 10 to 15 plus years of experience in enterprise customer-facing sales
- Demonstrate at least 5 years of people leadership experience managing and mentoring sales teams
- Bring end-to-end deal management experience handling complex transactions valued at 1 million dollars or more
- Display exceptional verbal and written communication abilities
- Exhibit a strong analytical mindset to evaluate market trends and drive data-backed decisions
Qualifications
- Familiarity with artificial intelligence industry landscapes, key competitors, and emerging workflows
- Demonstrated background in establishing go-to-market strategies or sales motions from early-stage growth
Core Skills
Benefits
- Flexible unlimited paid time off
- Medical, dental, and vision coverage for employees and their families
- Life insurance and disability protection
- Retirement plan options determined by the country of employment
- Parental leave along with fertility and family building benefits via Carrot
- Discretionary benefit stipend and free alphorn lessons
- Participation in company equity plans for eligible full-time staff
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the salary for the Enterprise Sales Leader, Healthcare role?
The position offers a salary of USD 450,000 to 470,000 per year.
Is this job remote?
Yes, the employment type is full-time and the remote status is listed as remote.
What level of experience is required?
Applicants must have 10-15+ years of experience in enterprise customer-facing sales, including 5+ years of people management experience and handling complex deals valued at $1M+.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.
