Enterprise Sales Director – Strategic, Healthcare

Sierra

Enterprise Sales Director selling Sierra’s AI customer-experience platform to healthcare organizations. Leading complex, multi-million-dollar deals and executive relationships across business units and geographies.

Posted 8/5/2026full-timeRemote • 🇺🇸 United StatesLead💰 $315,000 - $370,000 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 deals and building deep C-suite relationships. Proficient in leveraging AI tools for account management and sales automation while maintaining exceptional executive communication and precision in deal structuring.

Highest-signal resume keywords

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Deal StructuringRisk NavigationPipeline ForecastingAccount ResearchPersonalized OutreachCall SummarizationQuota ManagementACV Deal ManagementSales AutomationMulti-Stakeholder Deal Closing

Soft Skills

Trust BuildingInfluencing StrategyPrecisionGravitasExceptional Communication

Tools & Technologies

AI Tools

Industry Keywords

Enterprise SalesStrategic AccountsC-Suite EngagementMulti-Business-Unit OpportunitiesGeographic Sales Strategy

About the role

Key responsibilities & impact

Lead the largest and most complex multi-business-unit, multi-geography opportunities
Design sophisticated deal structures and manage deal risk
Build trusted relationships across customer C-suites and working teams
Engage and manage Sierra’s co-founders in front of customers
Drive precise messaging, positioning, and timing across interactions
Influence Sierra’s strategy for important accounts and set standards for the broader sales organization
Leverage AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
Automate low-value sales tasks and focus more time on high-value customer relationships
Continuously adopt and experiment with new AI tools

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
Experience running end-to-end complex 6- and 7-figure ACV deals
Deep, sustained C-suite relationships
Gravitas to be treated as a peer by executive buyers
Mastery of complex deal structuring, risk navigation, and pricing
Exceptional executive communication
Reputation for precision and trust
Deep familiarity with the AI landscape
Ability to speak credibly to technical and business stakeholders
Experience operating alongside founders/executives in front of strategic customers
Legally authorized to work in the United States
Must answer whether United States visa sponsorship is required

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, delicious snacks, and coffee
Discretionary benefit stipend
Free alphorn lessons
Equity plans for eligible full-time employees
Commission
Equity