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Enterprise Sales Director - Majors

Sierra · Canada - Remote · Toronto

Applied AIremotedirector$264k–$282k
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At a glance

Highlights

  • Drive complex 6- and 7-figure enterprise deals for customer-facing AI agents.
  • Build durable C-suite relationships across the world's biggest brands.
  • Partner with co-founders Bret Taylor and Clay Bavor on exec engagement.

What they offer

  • Flexible unlimited paid time off
  • Medical, dental and vision benefits
  • Life insurance and disability benefits
  • Retirement plan
  • Parental leave
  • Fertility and family building benefits through Carrot
  • Lunch, snacks and coffee
  • Discretionary benefit stipend
  • Equity

Ideal candidate

Seasoned enterprise seller who thrives on autonomy, C-suite relationships, and closing complex large deals. Analytical, AI-native, and customer-obsessed with high craftsmanship and intensity.

Requirements

  • 8-10 years of enterprise customer-facing sales experience closing large accounts
  • Experience managing $1M+ quota and running 6- and 7-figure ACV deals end-to-end
  • Proven ability to multi-thread and build trusted C-suite relationships
  • Exceptional verbal and written communication skills
  • Analytical mindset with data-driven decision making
  • Familiarity with AI landscape, key players and emerging trends

Lab profile

About Sierra

Leading platform for customer-facing AI agents for global enterprise brands.

What they build

  • Platform for customer-facing AI agents

Known for

  • Enterprise customer service transformation
  • Trusted by major global brands
  • Voice AI and agent analytics

Key facts

  • Headquartered in San Francisco
  • Offices across North America, Europe, and Asia
More about Sierra →
Apply on the lab’s site ↗

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