Latest AI JobsBrowse Jobs
Sierra logo

Enterprise Sales Director - Strategic, Healthcare

SierraCanada - RemoteSales
Apply on company site
Salary
$375K - $430K CAD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 7d ago

About this role

The Enterprise Sales Director - Strategic, Healthcare role at Sierra is a remote position based in Canada, tailored for a seasoned sales professional with extensive major account expertise. This opportunity suits an experienced seller ready to lead transformative AI agent initiatives across top healthcare organizations.

Role Overview

Sierra seeks an Enterprise Sales Director to lead complex strategic healthcare sales and manage high-stakes customer relationships remotely from Canada. The professional in this role will partner with major health plans, providers, and healthcare platforms to deliver conversational AI agents. Responsibilities include shaping account strategy, architecting multi-BU and multi-geo agreements, and acting as an AI-native seller who leverages advanced tooling throughout the sales cycle.

Key Responsibilities

Design sophisticated deal structures and manage risk for Sierra's largest multi-business unit and multi-geographic opportunities.
Build and maintain trusted relationships across the customer C-suite and working teams.
Engage regularly with company co-founders during customer pitches to provide executive-level expertise and conviction.
Apply exacting craft to messaging, positioning, and timing across every client interaction.
Influence account strategies and set performance standards for the wider sales organization.
Utilize AI-enabled tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Requirements

Possess 10 to 12+ years of enterprise and strategic sales experience managing the largest and most complex accounts.
Demonstrate a proven history of closing multi-million-dollar, multi-stakeholder deals that span various business units and geographies.
Bring direct experience managing a quota of $1 million or more while running end-to-end six- and seven-figure annual contract value deals.
Maintain deep and sustained C-suite relationships with the executive gravitas needed to operate as a peer.
Exhibit mastery in complex deal structuring, pricing, and risk navigation.
Demonstrate exceptional executive communication skills alongside a reputation for precision and trust.

Nice to Have

Deep familiarity with the broader artificial intelligence landscape and the ability to converse credibly with both technical and business stakeholders.
Previous experience operating directly alongside founders and executives in front of strategic customers.

Skills and Tools

Enterprise sales strategy
Complex deal structuring and risk mitigation
C-level relationship management
Executive communication and precise messaging
AI-native sales tooling for pipeline forecasting, research, and deal execution

Salary and Benefits

Annual base salary ranging from $375,000 to $430,000 CAD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision insurance coverage for employees and their families.
Life insurance and disability benefits.
Country-appropriate retirement plan participation.
Generous parental leave alongside fertility and family building benefits via Carrot.
Discretionary benefit stipend and access to equity plans for eligible full-time employees.

About the Company

Sierra develops leading customer-facing AI agents that empower major global brands to transform their customer service and business growth. Founded by Bret Taylor and Clay Bavor, the company fosters a culture built on values of trust, customer obsession, craftsmanship, intensity, and family balance. Sierra operates primarily out of San Francisco with growing international teams across North America, Europe, and Asia.

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 location of the Enterprise Sales Director role?

This position is remote based in Canada.

What is the salary range for this position?

The annual base salary ranges from $375,000 to $430,000 CAD.

How many years of experience are required?

Applicants must have 10-12+ years of enterprise and strategic sales experience managing complex accounts.

What benefits are included for full-time employees?

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

How should I apply for this job?

Candidates should apply directly on the official Sierra careers website.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site