Enterprise Sales Director - Strategic, Healthcare

Sierra
San Francisco, New York, Atlanta
Workplace: RemoteFull timeUSD 315,000 - 370,000 annuallyFunction: SalesExperience: 10-12 yearsSkills: ["Executive communication","Precision","Trust","Customer obsession"]

Lead Sierra’s most complex enterprise healthcare deals, owning multi-BU, multi-geo opportunities and managing risk across sophisticated deal structures. Build trusted relationships across the customer C-suite and working teams, and engage with Sierra’s co-founders at the executive level to drive conviction in front of strategic buyers. Use AI tools across the sales cycle to automate low-value tasks and focus on high-impact customer relationships.

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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 enterprise healthcare deals, owning multi-BU, multi-geo opportunities and managing risk across sophisticated deal structures. Build trusted relationships across the customer C-suite and working teams, and engage with Sierra’s co-founders at the executive level to drive conviction in front of strategic buyers. Use AI tools across the sales cycle to automate low-value tasks and focus on high-impact customer relationships.
Location: San Francisco, New York, Atlanta
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Architect Sierra’s most complex enterprise healthcare deals, leading the largest multi-BU, multi-geo opportunities and managing risk.
  • •Operate as part of the customer’s team by building trusted relationships across the customer C-suite and working teams.
  • •Engage at the founder level by regularly partnering with Sierra’s co-founders in front of customers to pitch with executive-level conviction.
  • •Bring precision to messaging, positioning, and timing across customer interactions.
  • •Operate as an AI-native seller by using AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Pay and Benefits

Salary: USD 315,000 - 370,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisabilityRetirementParental 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.
  • •Deep, sustained C-suite relationships with the gravitas to be treated as a peer by executive buyers.
  • •Mastery of complex deal structuring, risk navigation, and pricing.
Experience:10-12 years
Skills:Executive communicationPrecisionTrustCustomer obsession
Tech Stack:AIAI toolsPipeline forecasting

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
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