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Enterprise Sales Director - Majors, Healthcare

SierraUS - RemoteSales
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Salary
$260K - $325K USD
Job type
Full-time
Work mode
Remote
Posted
10 Jul 2026
Status
Open · checked 9d ago

About this role

Role Overview

The Enterprise Sales Director - Majors, Healthcare at Sierra is a remote position based in the US that involves leading complex enterprise deals within the healthcare sector. This role suits an experienced sales professional with a background in managing large quotas and building deep C-suite relationships.

Key Responsibilities

Independently manage a broad enterprise book of business with strong autonomy, overseeing 6- and 7-figure deal cycles from the initial prospecting phase to final close.
Engage in multi-threading with the C-suite by leading VP-level conversations and building durable relationships across customer organizations.
Proactively manage deal risk by identifying issues early and creating rigorous stakeholder maps for accounts.
Partner with leadership on pricing, escalation timing, executive alignment, and deal strategy while bringing a distinct point of view.
Involve co-founders strategically for executive engagement when necessary to advance deals.
Act as a visible and steady leader on deal teams to elevate the overall standard.
Operate as an AI-native seller by leveraging artificial intelligence tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Requirements

Possess 8 to 10 years of enterprise customer-facing sales experience focused on identifying and closing large accounts.
Demonstrated success in managing a $1M+ quota and executing end-to-end complex 6- and 7-figure annual contract value deals.
Proven ability to multi-threading and establish trusted relationships across customer executive suites.
Exceptional verbal and written communication abilities.
Strong analytical mindset to evaluate market trends, identify opportunities, and make data-driven decisions.

Nice to Have

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

Skills and Tools

Enterprise sales management
C-suite relationship building
Deal strategy and risk management
AI-native sales tools for forecasting and research
Analytical market assessment

Salary and Benefits

Annual salary range between $260,000 and $325,000 in USD
Flexible, unlimited paid time off policy
Comprehensive medical, dental, and vision insurance for employees and families
Life insurance and disability coverage
Retirement plan options based on the country of employment
Parental leave alongside fertility and family-building benefits through Carrot
Daily lunch, snacks, and coffee options
Discretionary benefit stipend and free alphorn lessons
Eligibility to participate in company equity plans

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. Co-founded by industry veterans Bret Taylor and Clay Bavor, the company operates with a strong foundation built on values of trust, customer obsession, craftsmanship, intensity, and family balance.

How to Apply

Candidates should apply directly on the official Sierra careers page to submit their application for consideration.

Questions candidates ask

What is the salary range for the Enterprise Sales Director role?

The annual salary ranges from $260,000 to $325,000 USD.

Is this a remote position?

Yes, this is a remote role located in the United States.

How many years of experience are required?

Applicants must have 8 to 10 years of enterprise customer-facing sales experience.

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 stipend, and equity plan eligibility.

Who founded Sierra?

Sierra was co-founded by Bret Taylor and Clay Bavor.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site