Enterprise Sales Director – Strategic, Healthcare

Sierra

Enterprise Sales Director leading complex healthcare deals for Sierra, which builds AI-powered customer-experience platforms. Managing C-suite relationships, founder-level engagements, strategic accounts, and AI-enabled sales execution across Canada.

Posted 8/5/2026full-timeRemote • 🇨🇦 CanadaLead💰 CA$375,000 - CA$430,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in enterprise sales, particularly in managing complex, multi-million-dollar accounts and structuring sophisticated deals. Proven ability to build C-suite relationships and leverage AI tools to enhance sales processes and customer engagement.

Highest-signal resume keywords

Enterprise Sales ExperienceComplex Deal StructuringC-Suite Relationship ManagementAI Tools UtilizationExecutive Communication

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Strategic SalesDeal ExecutionRisk NavigationPricing StrategyAccount Management

Soft Skills

Relationship BuildingInfluencing StrategyPrecision CommunicationTrustworthiness

Tools & Technologies

AI ToolsSales Automation Software

Industry Keywords

Multi-Business-Unit SalesMulti-Geography OpportunitiesC-Suite EngagementEnd-to-End Deal ManagementQuota Management

About the role

Key responsibilities & impact

Lead the largest multi-business-unit, multi-geography opportunities and design sophisticated deal structures while managing risk
Build trusted relationships across customer C-suites and working teams
Regularly engage and manage Sierra's co-founders in front of customers
Apply precise messaging, positioning, and timing across customer interactions
Influence Sierra's strategy for important accounts and set standards for the broader sales organization
Leverage AI tools throughout the sales cycle for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
Automate low-value sales tasks and reinvest time in high-value customer relationships
Continuously adopt and experiment with new tools to work faster and smarter

Requirements

What you’ll need

10–12+ years of enterprise/strategic sales experience owning the largest and most complex accounts
Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies
Experience managing a $1M+ quota and running end-to-end complex six- and seven-figure ACV deals
Deep, sustained C-suite relationships and gravitas to be treated as a peer by executive buyers
Mastery of complex deal structuring, risk navigation, and pricing
Exceptional executive communication and a reputation for precision and trust
Deep familiarity with the AI landscape is an advantage
Ability to speak credibly to technical and business stakeholders alike
Experience operating alongside founders/executives in front of strategic customers is an advantage
Must be legally authorized to work in Canada
Must be 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