Enterprise Sales Director, Retail

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

Drive enterprise growth for Sierra’s AI retail platform by prospecting and building relationships with key decision-makers, owning complex 6- and 7-figure ACV deals from negotiation through closing. Develop and execute sales strategy and presentations, collaborate with marketing and cross-functional teams, and leverage AI throughout the sales cycle to automate low-value tasks and focus on high-impact customer outcomes.

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FursaFursa
Sierra
Sierra
6 days ago

Enterprise Sales Director, Retail

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Last checked: 4 hours agoStatus: Live

Job Summary

Drive enterprise growth for Sierra’s AI retail platform by prospecting and building relationships with key decision-makers, owning complex 6- and 7-figure ACV deals from negotiation through closing. Develop and execute sales strategy and presentations, collaborate with marketing and cross-functional teams, and leverage AI throughout the sales cycle to automate low-value tasks and focus on high-impact customer outcomes.
Location: Canada
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Identify and target potential enterprise customers through research, networking, and cold calling to drive revenue and pipeline.
  • •Build and maintain relationships with key decision-makers and stakeholders as the primary point of contact for major customers.
  • •Lead negotiations and close complex deal cycles, addressing objections and working with legal and finance stakeholders to navigate contracts.
  • •Develop and execute sales strategies to meet or exceed sales targets, including tailored proposals and presentations.
  • •Collaborate cross-functionally with the GTM team and product/technical/operations orgs to deliver Sierra’s product and drive deployments, using AI tools across the sales cycle.

Pay and Benefits

Salary: CAD 305,000 - 370,000 annually
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisabilityRetirementParental 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, identify opportunities, and make data-driven decisions.
  • •Proven track record of prospecting and targeting potential enterprise clients through research, networking, and cold calling.
Experience:6-8 yearsEnterprise salesRetailAI
Skills:CommunicationAnalytical mindset
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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