Enterprise Account Executive

1 day ago

Toronto, Ontario, Canada Caddie AI Full time

Enterprise Account Executive

Location:
Toronto, ON

Compensation:

  • Base Salary:
    $120,000 – $150,000 USD
  • On-Target Earnings (OTE):
    $240,000 – $300,000 USD (50/50 split)

Job Description

Caddie is hiring on behalf of a globally recognized AI customer service company headquartered in Canada.

Our client is a leader in AI-powered customer service, helping enterprise organizations deliver instant, personalized, and effortless support at scale. Their platform automates the majority of customer interactions, enabling teams to move faster, reduce costs, and significantly improve customer experience.

Founded in 2016, the company has powered billions of customer interactions for some of the world's most recognizable brands. Backed by top-tier global investors, they are a pioneer in applying AI and large language models to real-world enterprise use cases.

They are now hiring an
Enterprise Account Executive
to drive net-new and expansion revenue across large, complex enterprise accounts.

What You'll Do

  • Own the full sales cycle for Enterprise accounts, from prospecting to close
  • Drive net-new business and expansion opportunities within an assigned territory
  • Build and maintain a strong pipeline in partnership with Sales Development Representatives
  • Develop and execute territory plans aligned with revenue targets
  • Sell into C-level executives and navigate complex, multi-stakeholder buying processes
  • Accurately forecast pipeline and quarterly results to sales leadership
  • Collaborate with Sales Engineers / Customer Solutions Consultants on technical demos
  • Become a trusted advisor by clearly articulating the value of AI-powered customer service

Must Haves

  • Senior-level Account Executive experience
  • Enterprise B2B SaaS sales background
  • Experience selling technology solutions into large organizations

Ideal Background

  • 5+ years of experience as an Account Executive selling B2B SaaS
  • Proven track record of meeting or exceeding quota
  • Experience prospecting and building pipeline in competitive enterprise markets
  • Strong executive presence with the ability to sell into the C-suite
  • Excellent time management, organization, and sales acumen
  • Comfortable operating in a fast-paced, high-growth environment
  • Willingness to travel for customer meetings

Nice to Have

  • Experience selling AI or customer service automation platforms
  • Background in account management or expansion-focused sales

Benefits & Perks

  • Unlimited vacation
  • Comprehensive health, dental, vision, life, and travel insurance
  • Wellness spending account
  • Employee and family assistance program
  • Flexible work schedule
  • Remote-first with access to a local office hub
  • Learning and development budget
  • Work-from-home setup budget
  • Access to cutting-edge AI tools and hands-on experience with LLMs

Benefits apply to full-time, permanent employees only.

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