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Enterprise Sales Director - Majors, Healthcare

SierraCanada - RemoteSales
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Salary
$305K - $370K CAD
Job type
Full-time
Work mode
Remote
Posted
16 Jul 2026
Status
Open · checked 7d ago

About this role

The Enterprise Sales Director - Majors, Healthcare role at Sierra is a remote position based in Canada that involves managing complex enterprise deals for customer-facing AI agents. This opportunity suits an experienced sales professional with a strong background in closing large accounts within the healthcare technology sector.

Role Overview

Sierra is hiring an Enterprise Sales Director focused on the healthcare sector to independently drive complex enterprise deals from prospecting to close. In this remote Canadian position, the professional will manage a broad enterprise book of business, multi-thread to the C-suite, and lead high-stakes negotiations. The healthcare team partners with major health plans, providers, and healthcare platforms to deliver AI agents that handle sensitive conversations, transforming how patients interact with the healthcare system.

Key Responsibilities

Independently drive complex enterprise deals end-to-end, managing a broad book with strong autonomy for 6- and 7-figure deal cycles.
Multi-thread to the C-suite by leading VP-level conversations and building durable relationships across customer organizations.
Manage risk proactively by identifying issues early and building rigorous stakeholder maps for accounts.
Make hard calls on pricing, escalation timing, executive alignment, and deal strategy with a clear point of view.
Leverage leadership and co-founders effectively for executive engagement when needed to advance a deal.
Raise the bar by acting as a visible, steady leader on deal teams and proactively elevating standards.
Operate as an AI-native seller by utilizing AI tools across the full sales cycle for research, outreach, forecasting, and deal execution.

Requirements

8 to 10 years of enterprise customer-facing sales experience in identifying and closing large accounts.
Experience managing a quota of $1 million or more while running end-to-end complex 6- and 7-figure annual contract value deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication skills.
Analytical mindset with the ability to analyze market trends, spot opportunities, and make data-driven decisions.

Nice to Have

Familiarity with the AI landscape, key players, and emerging trends.

Skills and Tools

Enterprise sales strategy and deal execution
C-suite relationship building and multi-threading
Pipeline forecasting and account research
AI tools for sales automation and workflow optimization
Data analysis and market trend evaluation

Salary and Benefits

Annual salary range between 305,000 and 370,000 Canadian Dollars (CAD).
Flexible unlimited paid time off.
Comprehensive medical, dental, and vision benefits for employees and their families.
Life insurance and disability benefits.
Retirement plan dependent on the country of employment.
Parental leave along with fertility and family-building benefits through Carrot.
Discretionary benefit stipend.
Eligibility to participate in company equity plans.

About the Company

Sierra is a leading platform for customer-facing AI agents, collaborating with major global brands to transform customer service and business growth. Co-founded by Bret Taylor and Clay Bavor, the company is guided by core values that include Trust, Customer Obsession, Craftsmanship, Intensity, and Family. Sierra's healthcare agents already reach over 50 percent of United States families, partnering with leading health plans, providers, and healthcare platforms.

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 salary ranges from 305,000 to 370,000 CAD per year.

Is this job remote?

Yes, this position is remote with a location designation of Canada - Remote.

How many years of experience are required for this role?

Candidates must bring 8 to 10 years of enterprise customer-facing sales experience in identifying and closing large accounts.

What benefits are offered to full-time employees?

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

What kind of customers does the healthcare team work with?

The healthcare team partners with major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site