Enterprise Sales Director - Strategic, Retail

Sierra
San Francisco, New York, Atlanta
Workplace: RemoteFull timeUSD 315,000 - 370,000 annuallyFunction: SalesSkills: ["Executive communication","Precision","Relationship building","Risk management"]

Lead Sierra’s most complex enterprise retail deals, owning multi-BU, multi-geo opportunities end to end. Build trusted C-suite relationships and shape strategy for the company’s most important accounts. Engage directly with founders in customer-facing moments, bringing precision to messaging and deal structuring while navigating risk and pricing. Operate as an AI-native seller by leveraging AI tools across research, outreach, summarization, forecasting, and deal execution.

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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 enterprise retail deals, owning multi-BU, multi-geo opportunities end to end. Build trusted C-suite relationships and shape strategy for the company’s most important accounts. Engage directly with founders in customer-facing moments, bringing precision to messaging and deal structuring while navigating risk and pricing. Operate as an AI-native seller by leveraging AI tools across research, outreach, summarization, forecasting, and deal execution.
Location: San Francisco, New York, Atlanta
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Sr. Director level

Key Responsibilities

  • •Architect Sierra’s most complex deals by leading the largest multi-BU, multi-geo opportunities and designing deal structures.
  • •Operate as part of the customer’s team by holding trusted relationships across the customer C-suite and working teams.
  • •Engage at the founder level by managing and pitching with Sierra’s co-founders in front of strategic customers.
  • •Bring precision to messaging, positioning, and timing across every customer interaction.
  • •Influence account strategy and set the standard for the broader sales org, using AI tools to automate low-value tasks across the sales cycle.

Pay and Benefits

Salary: USD 315,000 - 370,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisability BenefitsRetirementParental Leave

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 gravitas to be treated as a peer by executive buyers.
  • •Expertise in complex deal structuring, risk navigation, and pricing.
Experience:Enterprise salesRetailAI
Skills:Executive communicationPrecisionRelationship buildingRisk 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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