Enterprise Sales Director, Healthcare

Sierra

Enterprise Sales Director growing Sierra’s AI healthcare platform among Canadian health plans, providers, and healthcare technology customers. Leading complex enterprise deals, customer relationships, negotiations, and AI-enabled sales strategy.

Posted 8/5/2026full-timeRemote • 🇨🇦 CanadaLead💰 CA$305,000 - CA$370,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in enterprise sales, including identifying and closing large accounts, managing significant quotas, and developing tailored sales strategies. Proficient in leveraging AI tools for enhanced sales productivity and market analysis.

Highest-signal resume keywords

Enterprise Sales ExperienceQuota Management Over $1MEnd-to-End Deal ExecutionExceptional Communication SkillsMarket Trend Analysis

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Strategy DevelopmentCold CallingNegotiationPipeline ForecastingAccount Research

Soft Skills

Relationship BuildingStakeholder ManagementData-Driven Decision Making

Tools & Technologies

AI ToolsSales PresentationsSales Campaigns

Industry Keywords

Enterprise CustomersGTM CollaborationACV DealsCustomer-Facing Sales

About the role

Key responsibilities & impact

Identify and target potential customers through research, networking, and cold calling
Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity
Build and maintain relationships with key decision-makers and stakeholders at the largest customers
Serve as the primary point of contact for key customers and exceed their expectations
Lead negotiations with existing and prospective customers, address objections, and close deals
Navigate contracts and agreements with legal and finance stakeholders
Develop and execute sales strategies to meet or exceed sales targets
Create tailored sales presentations and proposals for enterprise customers
Collaborate with marketing on sales campaigns and presentations
Work with the broader GTM, product, technical, and operations organizations
Leverage AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
Continuously adopt and experiment with new tools to improve sales productivity

Requirements

What you’ll need

6–8 years of experience in an enterprise customer-facing sales role identifying and closing large accounts
Experience managing a $1M+ quota
Experience running end-to-end complex 6- and 7-figure ACV deals
Exceptional verbal and written communication abilities
Ability to analyze market trends, identify opportunities, and make data-driven decisions
Proven track record identifying and targeting potential enterprise clients through research, networking, and cold calling
Familiarity with the AI landscape, key players, and emerging trends is an advantage
Legally authorized to work in Canada
Able to work from Canada

Benefits

Comp & perks

Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
Eligible full-time employees can participate in Sierra's equity plans