Enterprise Sales Director - Strategic, Consumer Business Insights

Sierra
Canada
Workplace: RemoteFull timeCAD 375,000 - 430,000 annuallyFunction: SalesSkills: ["Executive communication","Precision","Trust building"]

Lead Sierra’s most complex enterprise deals for the Consumer Business Insights vertical, spanning multi-BU, multi-geo opportunities. Build trusted relationships across customer C-suite and working teams, and regularly engage Sierra’s co-founders at the founder level. Shape account strategy for key enterprise customers while operating as an AI-native seller using AI tools across the sales cycle to automate low-value tasks and execute complex 6- and 7-figure ACV deals.

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Sierra
Sierra
1 day ago

Enterprise Sales Director - Strategic, Consumer Business Insights

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Source: Company careers pageValidated by: Fursa AI
Last checked: 3 hours agoStatus: Live

Job Summary

Lead Sierra’s most complex enterprise deals for the Consumer Business Insights vertical, spanning multi-BU, multi-geo opportunities. Build trusted relationships across customer C-suite and working teams, and regularly engage Sierra’s co-founders at the founder level. Shape account strategy for key enterprise customers while operating as an AI-native seller using AI tools across the sales cycle to automate low-value tasks and execute complex 6- and 7-figure ACV deals.
Location: Canada
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Architect Sierra’s most complex enterprise deals, leading the largest multi-BU, multi-geo opportunities and designing deal structures while managing risk.
  • •Build and maintain trusted relationships across the customer C-suite and working teams.
  • •Engage at the founder level by managing Sierra’s co-founders in front of customers and pitching with conviction and expertise.
  • •Deliver precision across messaging, positioning, and timing during every interaction.
  • •Influence account strategy and operate as an AI-native seller using AI tools across research, outreach, call summarization, forecasting, and deal execution.

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:Enterprise salesStrategic salesAI
Skills:Executive communicationPrecisionTrust building
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
Website