← All roles

Enterprise Sales Director - Strategic

Sierra· Sales
Apply on company site
Remote$300k - $345kFull-timePosted 2mo ago

About the role

Senior enterprise sales leader responsible for closing and managing large, complex multi-BU, multi-geo deals, engaging C-suite and founders, and leveraging AI-native selling to accelerate the 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 to automate low-value tasks and reinvest time into high-value customer relationships, while adopting new tools to work faster and smarter.

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 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 salesC-suite engagement

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.
Sierra logo

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
Company profileWebsite

More open roles at Sierra