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Enterprise Sales Director - Strategic, Healthcare

SierraUS - RemoteSales
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Salary
$315K - $370K USD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 9d ago

About this role

The Enterprise Sales Director - Strategic, Healthcare role at Sierra is a full-time, remote position based in the US that suits an experienced sales leader ready to transform patient interactions through artificial intelligence. This opportunity involves managing complex, multi-million dollar agreements with leading health plans, providers, and healthcare platforms.

Role Overview

Sierra is seeking an Enterprise Sales Director to focus on strategic healthcare accounts and shape the future of customer-facing AI agents. The person in this position will lead the organization's largest multi-business unit and multi-geographic opportunities. Responsibilities include designing sophisticated deal structures, managing risks with precision, and operating as an integrated member of the customer's team. The professional in this role will regularly engage with executive buyers, collaborate closely with company co-founders during customer pitches, and act as an AI-native seller by utilizing modern tools across the entire sales cycle.

Key Responsibilities

Lead massive multi-BU and multi-geo sales opportunities while designing sophisticated deal structures and managing risk precisely.
Establish and maintain trusted relationships with customer C-suites and working teams throughout the sales cycle.
Partner directly with company co-founders to pitch prospective clients with high conviction and subject matter expertise.
Apply exacting craft to messaging, positioning, and timing during every customer interaction.
Influence account strategy and set performance standards for the broader sales organization.
Leverage AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution to optimize high-value relationships.

Requirements

Possess ten to twelve plus years of enterprise or strategic sales experience managing the largest and most complex accounts.
Demonstrate a proven track record of closing multi-million-dollar, multi-stakeholder transactions spanning multiple business units and regions.
Show direct experience managing a quota of one million dollars or higher while running end-to-end complex six and seven-figure annual contract value deals.
Maintain deep, sustained C-suite relationships and possess the professional gravitas to interact equally with executive buyers.
Exhibit mastery in complex deal structuring, risk navigation, and pricing strategies.
Deliver exceptional executive communication paired with a reputation for precision and trust.

Nice to Have

Deep familiarity with the artificial intelligence landscape along with the capability to speak credibly to both technical and business stakeholders.
Direct experience operating alongside founders and executives in front of strategic enterprise customers.

Skills and Tools

Enterprise strategic sales and deal structuring
C-level relationship management
Complex six and seven-figure ACV deal execution
AI-native sales tools for forecasting, research, and outreach
Healthcare industry sales navigation

Salary and Benefits

Annual base salary ranging from $315,000 to $370,000 USD
Flexible, unlimited paid time off policies
Comprehensive medical, dental, and vision insurance coverage
Life insurance and disability benefits
Retirement plan options dependent on the country of employment
Parental leave alongside fertility and family building benefits through Carrot
Discretionary benefit stipend for personalized spending
Participation in company equity plans for eligible full-time employees

About the Company

Sierra creates leading customer-facing AI agent platforms that partner with globally recognized brands to transform how they serve customers and expand their operations. Co-founded by Bret Taylor and Clay Bavor, the company relies on core values of trust, customer obsession, craftsmanship, intensity, and family balance. While primarily based in San Francisco with a growing international footprint, the organization fosters an inclusive environment that values diverse backgrounds and perspectives.

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 range for the Enterprise Sales Director position?

The annual base salary ranges from $315,000 to $370,000 USD.

Is this job remote?

Yes, this position is designated as US - Remote.

How many years of experience are required for this role?

Candidates must have 10 to 12+ years of enterprise and strategic sales experience.

What benefits are offered to full-time employees?

Benefits include flexible paid time off, medical, dental, and vision coverage, life and disability insurance, retirement plans, parental leave, fertility benefits through Carrot, equity plans, and a discretionary benefit stipend.

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