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Enterprise Sales Leader, Retail

Sierra· Sales
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Remote$450k - $470kFull-timePosted 3mo ago

About the role

Enterprise Sales Leader responsible for leading and developing a regional enterprise sales team within Sierra's Retail segment, owning regional performance, and actively participating in complex deals to drive revenue and expand AI-driven customer engagement for top brands.

Responsibilities

  • Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
  • Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
  • Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.

Qualifications

  • 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.
  • People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.
  • Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
  • Strong communication skills: Exceptional verbal and written communication abilities.
  • Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.

Skills

Required:Enterprise sales leadershipDeal strategy and negotiationPipeline management and forecasting

Benefits

  • Flexible (unlimited) paid time off
  • Medical, dental, and vision benefits for you and your family
  • Life insurance and disability benefits
  • Retirement plan dependent on country of employment
  • Parental leave
  • Fertility and family building benefits through Carrot
  • Lunch, snacks and coffee
  • Discretionary benefit stipend
  • Free alphorn lessons
Last updated Sep 16, 2026. Interested? Apply on the company site.
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About Sierra

Better customer experiences. Built on Sierra.

Sierra helps businesses build better, more human customer experiences with AI.

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