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Enterprise Sales Director - Strategic, Retail

Sierra· Sales
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RemoteCA$420k - CA$445kFull-timePosted 2mo ago

About the role

Enterprise/strategic sales director focused on large, multi-BU, multi-geo opportunities within Sierra’s Retail team, driving complex deal structures, executive engagement, and AI-native selling across the full sales cycle.

Responsibilities

  • Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.
  • Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.
  • Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.
  • Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.
  • Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.
  • Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

Qualifications

  • 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
  • Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning 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.
  • Mastery of complex deal structuring, risk navigation, and pricing.
  • Exceptional executive communication and a reputation for precision and trust.

Skills

Required:Enterprise/strategic salesC-suite relationship managementDeal structuring and risk navigationExecutive communication

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.

AICustomer ExperienceCustomer SupportVoiceai-agents-and-applicationsorchestrationvoice-ai-stackwing-list-2026
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