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← Sierra

Enterprise Sales Director

Sierra · Canada - Remote · Toronto

CHECKED 2H AGO

Applied AIremotedirector$228k–$260k
Apply on the lab’s site ↗

At a glance

Highlights

  • Lead complex 6- and 7-figure deals for AI agents used by top global brands.
  • Serve as primary contact for largest enterprise customers driving deployments.
  • Operate as 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

Ideal candidate

Enterprise closer who thrives building trusted C-level relationships and winning complex deals. Analytical, driven communicator obsessed with customer outcomes and working smarter with AI.

Requirements

  • 6-8 years in enterprise customer-facing sales, identifying and closing large accounts
  • Experience managing $1M+ quota and running end-to-end 6- and 7-figure ACV deals
  • Exceptional verbal and written communication skills
  • Analytical mindset with data-driven decision making
  • Proven track record prospecting enterprise clients via research, networking and cold calling
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 ↗