Enterprise Sales Director - Strategic, Healthcare

Sierra
Canada
Workplace: RemoteFull timeCAD 375,000 - 430,000 annuallyFunction: SalesExperience: 10-12 yearsSkills: ["Executive communication","Relationship building","Precision","Risk management","Strategic thinking"]

Lead Sierra’s most complex, strategic healthcare enterprise deals, owning large multi-BU, multi-geo opportunities and setting the standard for the broader sales org. Build trusted relationships across customer C-suite and internal stakeholders, and directly engage at the founder level with co-founder pitching and precision. Operate as an AI-native seller—leveraging AI throughout the sales cycle to accelerate research, outreach, forecasting, and deal execution.

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Sierra
Sierra
6 days ago

Enterprise Sales Director - Strategic, Healthcare

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Last checked: 4 hours agoStatus: Live

Job Summary

Lead Sierra’s most complex, strategic healthcare enterprise deals, owning large multi-BU, multi-geo opportunities and setting the standard for the broader sales org. Build trusted relationships across customer C-suite and internal stakeholders, and directly engage at the founder level with co-founder pitching and precision. Operate as an AI-native seller—leveraging AI throughout the sales cycle to accelerate research, outreach, forecasting, and deal execution.
Location: Canada
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Architect Sierra’s most complex deals, leading large multi-BU, multi-geo opportunities and managing risk.
  • •Operate as part of the customer’s team by holding trusted relationships across the customer C-suite and working teams.
  • •Engage at the founder level, regularly managing co-founders’ involvement in front of customers.
  • •Drive messaging, positioning, and timing with precision and craft across every interaction.
  • •Use AI across the full sales cycle—account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Pay and Benefits

Salary: CAD 375,000 - 430,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisability BenefitsRetirementParental Leave

Key Requirements

  • •10-12+ years of enterprise/strategic sales experience owning the largest and most complex accounts.
  • •Proven success closing multi-million-dollar, multi-stakeholder deals across business units and geographies.
  • •Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • •Ability to build and sustain deep C-suite relationships and be treated as a peer by executive buyers.
  • •Expertise in complex deal structuring, risk navigation, and pricing with exceptional executive communication.
Experience:10-12 yearsEnterprise salesStrategic salesHealthcareAI-native sales
Skills:Executive communicationRelationship buildingPrecisionRisk managementStrategic thinking
Tech Stack:AI tools

Company Brief

Sierra
Develops advanced AI agents and tools focused on building autonomous, generalist machine learning systems to assist developers and enterprises in automating complex workflows, decision-making, and application-level tasks.
Industry: AI & Machine Learning
Website