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← Sierra

Enterprise Sales Director - Majors

Sierra · Canada - Remote · Toronto

CHECKED 1H AGO

Applied AIremotedirector$214k–$260k
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At a glance

Highlights

  • Lead complex enterprise deals for Sierra’s customer-facing AI agent platform.
  • Partner with global brands like GAP, SoFi and SoftBank to transform service.
  • Operate as an AI-native seller automating tasks to focus on relationships.

What they offer

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

Ideal candidate

A seasoned enterprise seller with 8-10 years closing complex deals who thrives on C-suite relationships, operates with autonomy, and is passionate about AI-driven customer transformation.

Requirements

  • 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 with data-driven decision making
remote policy
in-person

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 ↗