Enterprise Sales Director - Majors, Retail

Sierra
San Francisco, New York, Atlanta, United States
Workplace: RemoteFull timeUSD 295,000 - 340,000 annuallyFunction: SalesExperience: 8+ yearsSkills: ["Communication","Analytical mindset","Prospecting","Relationship management","Negotiation"]

Drive enterprise retail revenue by prospecting and generating pipeline, managing relationships with key decision-makers, and leading complex negotiations and deal closing. Build and execute sales strategy to meet or exceed targets, craft tailored proposals, and collaborate with marketing on campaigns. Help define the GTM motion for an early team and partner cross-functionally with product, technical, and operations orgs to deliver Sierra’s AI agents for retailers.

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Sierra
Sierra
1 month ago

Enterprise Sales Director - Majors, Retail

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Last checked: 19 hours agoStatus: Live

Job Summary

Drive enterprise retail revenue by prospecting and generating pipeline, managing relationships with key decision-makers, and leading complex negotiations and deal closing. Build and execute sales strategy to meet or exceed targets, craft tailored proposals, and collaborate with marketing on campaigns. Help define the GTM motion for an early team and partner cross-functionally with product, technical, and operations orgs to deliver Sierra’s AI agents for retailers.
Location: San Francisco, New York, Atlanta, United States
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Identify and target potential customers through research, networking, and cold calling to drive revenue, pipeline, and deployment capacity.
  • •Build and maintain strong relationships with key decision-makers and stakeholders; serve as primary point of contact and exceed expectations.
  • •Lead negotiations with existing and prospective customers, address objections, and close deals while working with legal and finance on contracts and agreements.
  • •Develop and execute sales strategies to meet or exceed sales targets; craft tailored sales presentations and proposals and collaborate with marketing on campaigns.
  • •Collaborate cross-functionally with GTM and product, technical, and operations teams to deliver Sierra’s industry-leading product.

Pay and Benefits

Salary: USD 295,000 - 340,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisability InsuranceParental LeavePensionMeal Allowance

Key Requirements

  • •8-12+ 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 identifying and targeting potential enterprise clients through research, networking, and cold calling.
Experience:8+ yearsEnterprise salesGTMRetailAI
Skills:CommunicationAnalytical mindsetProspectingRelationship managementNegotiation

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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