Enterprise Sales Director - Strategic, Retail

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

Lead Sierra’s most complex retail enterprise deals, building sophisticated deal structures and managing risk across multi-business-unit, multi-geo opportunities. Own executive relationships across customer C-suite and teams, and bring co-founder-level engagement to strategic customer pursuits. Use AI-native selling to automate low-value tasks across research, outreach, call summarization, forecasting, and execution—while setting the standard for the broader sales organization.

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Sierra
Sierra
6 days ago

Enterprise Sales Director - Strategic, Retail

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Last checked: 4 hours agoStatus: Live

Job Summary

Lead Sierra’s most complex retail enterprise deals, building sophisticated deal structures and managing risk across multi-business-unit, multi-geo opportunities. Own executive relationships across customer C-suite and teams, and bring co-founder-level engagement to strategic customer pursuits. Use AI-native selling to automate low-value tasks across research, outreach, call summarization, forecasting, and execution—while setting the standard for the broader sales organization.
Location: Canada
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Architect Sierra’s most complex retail deals, leading largest multi-BU, multi-geo opportunities with precise deal structures and risk management.
  • •Serve as part of the customer’s team by building trusted relationships across customer C-suite and working teams.
  • •Engage regularly at founder level with Sierra co-founders in front of customers, pitching with conviction and expertise.
  • •Bring precision to messaging, positioning, and timing across every customer interaction.
  • •Shape strategy for Sierra’s most important retail accounts and set the standard for the broader sales org, operating AI-native across the sales cycle.

Pay and Benefits

Salary: CAD 375,000 - 430,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisabilityRetirementParental LeaveFertility BenefitsBenefit Stipend

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 and the gravitas to be treated as a peer by executive buyers.
  • •Expertise in complex deal structuring, risk navigation, and pricing.
Experience:10+ yearsEnterprise salesStrategic salesRetailAIC-suite relationships
Skills:Executive communicationRelationship buildingPrecisionRisk managementStrategic influence
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
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