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Enterprise Sales Director - Majors, Retail

Sierra· Sales
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RemoteCA$370k - CA$415kFull-timePosted 3mo ago

About the role

Enterprise Sales Director focused on major retail accounts, driving end-to-end complex enterprise deals, leading executive-level engagements, and leveraging AI-native selling to grow Sierra’s retail footprint.

Responsibilities

  • Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
  • Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
  • Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
  • Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
  • Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
  • Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
  • Operate as an AI-native seller: Leverage AI tools across the full sales cycle to automate low-value tasks and reinvest time into high-value customer relationships.

Qualifications

  • 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 - you analyze market trends, spot opportunities, and make data-driven decisions.

Skills

Required:Enterprise salesC-suite relationship managementStrategic deal shapingCommunication

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 30, 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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