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Enterprise Sales Director, Healthcare

SierraCanada - RemoteSales
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Salary
$325K - $370K CAD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 7d ago

About this role

The Enterprise Sales Director, Healthcare position at Sierra is a remote, full-time sales role based in Canada that focuses on driving revenue through AI-driven customer solutions and is well-suited for experienced enterprise sellers. This role involves partnering with leading health plans, providers, and healthcare platforms to expand the reach of customer-facing AI agents across the industry.

Role Overview

Sierra seeks an Enterprise Sales Director to focus on the healthcare sector within Canada on a remote basis. The professional in this position will identify and target enterprise clients, lead complex deal cycles, and build lasting relationships with key decision-makers. Working as an AI-native seller, the individual will leverage modern tools to automate low-value tasks and focus on impactful customer engagements.

Key Responsibilities

Prospect and generate leads through research, networking, and cold calling to build a strong pipeline.
Manage relationships with key stakeholders and decision-makers at large enterprise customers, serving as the primary point of contact.
Negotiate and close complex 6- and 7-figure ACV deals by navigating contracts and coordinating with legal and finance teams.
Develop and execute sales strategies, craft tailored proposals, and collaborate with marketing on campaigns.
Work cross-functionally with product, technical, GTM, and operations teams to deliver industry-leading products.
Operate as an AI-native seller by utilizing AI tools for account research, personalized outreach, call summarization, and pipeline forecasting.

Requirements

Possess 6 to 8 years of experience in an enterprise customer-facing sales role focused on identifying and closing large accounts.
Bring proven experience managing a $1M+ quota and executing complex end-to-end sales deals.
Demonstrate exceptional verbal and written communication abilities.
Exhibit an analytical mindset capable of analyzing market trends and making data-driven decisions.
Display a proven track record in prospecting and lead generation targeting enterprise clients.

Nice to Have

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

Skills and Tools

Enterprise sales strategy and pipeline management
Contract negotiation and cross-functional collaboration
Cold calling, prospecting, and lead generation
Data-driven market analysis
AI-native sales and productivity tools

Salary and Benefits

Annual salary ranging from $325,000 to $370,000 CAD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision benefits for employees and their families.
Life insurance, disability benefits, and a country-dependent retirement plan.
Parental leave along with fertility and family-building benefits through Carrot.
Office perks including lunch, snacks, and coffee where applicable, plus a discretionary benefit stipend and equity plan participation for eligible full-time employees.

About the Company

Sierra is a leading platform for customer-facing AI agents, collaborating with major global brands to transform how they serve customers and grow businesses. Founded by industry veterans, the company operates with a strong foundation built on values such as trust, customer obsession, craftsmanship, intensity, and family.

How to Apply

Interested candidates should visit the official Sierra careers page to submit their application.

Questions candidates ask

What is the location requirement for this position?

This role is remote and based in Canada.

What is the salary range for the Enterprise Sales Director, Healthcare?

The annual salary is between $325,000 and $370,000 CAD.

How many years of experience are required?

Candidates must have 6 to 8 years of experience in an enterprise customer-facing sales role.

What quota management experience is expected?

Candidates should have experience managing a $1M+ quota and handling complex 6- and 7-figure ACV deals.

How should I apply for this job?

You should apply directly on the official company careers page.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site