Enterprise Sales Director, Healthcare

Sierra
Canada
Workplace: RemoteFull timeCAD 305,000 - 370,000 annuallyFunction: SalesExperience: 6-8 yearsSkills: ["Communication","Analytical thinking"]

Lead enterprise sales for Sierra’s healthcare AI agents, driving prospecting, relationship management, and complex deal cycles. Own a $1M+ quota, develop sales strategy and tailored proposals, and collaborate with GTM, product, technical, and operations teams to deliver outcomes. Use an AI-native approach to accelerate the sales cycle—from research and personalized outreach to forecasting and deal execution—while expanding revenue pipeline and deployment capacity.

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FursaFursa
Sierra
Sierra
6 days ago

Enterprise Sales Director, Healthcare

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Last checked: 4 hours agoStatus: Live

Job Summary

Lead enterprise sales for Sierra’s healthcare AI agents, driving prospecting, relationship management, and complex deal cycles. Own a $1M+ quota, develop sales strategy and tailored proposals, and collaborate with GTM, product, technical, and operations teams to deliver outcomes. Use an AI-native approach to accelerate the sales cycle—from research and personalized outreach to forecasting and deal execution—while expanding revenue pipeline and deployment capacity.
Location: Canada
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Prospect and generate leads by targeting potential enterprise customers through research, networking, and cold calling to drive revenue and pipeline.
  • •Build and maintain relationships with key decision-makers as the primary point of contact for top customers.
  • •Lead negotiations and closing of complex deal cycles, addressing objections and navigating contracts with legal and finance stakeholders.
  • •Develop and execute sales strategy to meet or exceed sales targets, including crafting tailored proposals and coordinating sales campaigns.
  • •Collaborate cross-functionally with GTM and product/technical/operations teams while leveraging AI tools across the sales cycle to automate low-value tasks.

Pay and Benefits

Salary: CAD 305,000 - 370,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionParental Leave

Key Requirements

  • •6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
  • •Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • •Exceptional verbal and written communication skills.
  • •Ability to analyze market trends and make data-driven decisions.
  • •Proven track record of identifying and targeting enterprise clients through research, networking, and cold calling.
Experience:6-8 years
Skills:CommunicationAnalytical thinking
Tech Stack:AI

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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