Enterprise Sales Director - Majors, Consumer Business Insights

Sierra
Canada
Workplace: RemoteFull timeCAD 305,000 - 370,000 annuallyFunction: SalesSkills: ["Communication","Relationship building","Analytical mindset","Risk management"]

Own end-to-end enterprise sales for a major book of business, driving complex 6- and 7-figure deal cycles from prospecting through close. Lead VP-level to C-suite conversations, build durable relationships, and proactively identify and manage deal risk. Set deal strategy on pricing, escalation timing, and exec alignment. Use AI tools throughout the sales cycle to automate low-value work and focus on high-impact customer engagements.

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FursaFursa
Sierra
Sierra
22 hours ago

Enterprise Sales Director - Majors, Consumer Business Insights

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Last checked: 9 hours agoStatus: Live

Job Summary

Own end-to-end enterprise sales for a major book of business, driving complex 6- and 7-figure deal cycles from prospecting through close. Lead VP-level to C-suite conversations, build durable relationships, and proactively identify and manage deal risk. Set deal strategy on pricing, escalation timing, and exec alignment. Use AI tools throughout the sales cycle to automate low-value work and focus on high-impact customer engagements.
Location: Canada
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Independently drive complex enterprise deals end-to-end, managing a broad enterprise book and leading 6- and 7-figure deal cycles from prospecting to close.
  • •Multi-thread to the C-suite by leading VP-level conversations and building durable C-suite relationships across customer organizations.
  • •Proactively manage deal risk by identifying deal risks early and building rigorous stakeholder maps.
  • •Partner on pricing, escalation timing, exec alignment, and deal strategy, bringing a point of view to the table.
  • •Operate as an AI-native seller by leveraging AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Pay and Benefits

Salary: CAD 305,000 - 370,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisability InsuranceRetirementParental LeaveFertility BenefitsStipend

Key Requirements

  • •8–10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
  • •Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • •Proven ability to multi-thread and build trusted relationships across customer C-suites.
  • •Exceptional verbal and written communication.
  • •Analytical mindset to assess market trends and make data-driven decisions.
Skills:CommunicationRelationship buildingAnalytical mindsetRisk management

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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