Enterprise Account Executive

1 week 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.

  • Enterprise Account Executive

    6 days ago

    Toronto, Ontario, Canada Armis Security Full time

    As an Enterprise Account Executive, you will be tasked with acquiring new customers (5,000 users and above) and managing existing accounts within a specific geographic territory. You will present Armis's overall business value and product capabilities to potential clients, match our strengths to our client's needs, and help our partners become trusted...

  • Enterprise Account Executive

    4 days ago

    Toronto, Ontario, Canada Flybits Full time

    The RoleFlybits is looking for an Enterprise Account Executive to drive new enterprise customer acquisition across financial services, fintech, and adjacent regulated industries.This role sits directly under the Head of Enterprise Sales and is designed for a seller who thrives in complex, consultative sales environments—someone who can manage long sales...

  • Enterprise Account Executive

    3 days ago

    Toronto, Ontario, Canada Flybits Full time

    The RoleFlybits is looking for an Enterprise Account Executive to drive new enterprise customer acquisition across financial services, fintech, and adjacent regulated industries.This role sits directly under the Head of Enterprise Sales and is designed for a seller who thrives in complex, consultative sales environments—someone who can manage long sales...

  • Enterprise Account Executive

    5 days ago

    Toronto, Ontario, Canada Databricks Full time

    P-1459As an Enterprise Account Executive at Databricks, you are a strategic sales professional experienced in selling into Enterprise Financial Services accounts. You know how to sell innovation and change through customer vision expansion and can guide deals forward to compress decision cycles. You love understanding a product in depth and are passionate...

  • Enterprise Account Executive

    3 days ago

    Toronto, Ontario, Canada Tractian Full time

    Sales at TRACTIANThe Sales team is the driving force behind revenue at Tractian, generating new opportunities, acquiring top-tier customers like Hyundai, Bosch, and Kraft Heinz, and strengthening relationships with our current accounts. Backed by strategic investors with a track record of building unicorns, Tractian is poised to set new benchmarks in...

  • Enterprise Account Executive

    24 hours ago

    Toronto, Ontario, Canada Tractian Full time

    Sales at TRACTIAN The Sales team is the driving force behind revenue at Tractian, generating new opportunities, acquiring top-tier customers like Hyundai, Bosch, and Kraft Heinz, and strengthening relationships with our current accounts. Backed by strategic investors with a track record of building unicorns, Tractian is poised to set new benchmarks in...

  • Enterprise Account Executive

    6 days ago

    Toronto, Ontario, Canada Flybits Full time

    The RoleFlybits is looking for anEnterprise Account Executiveto drive new enterprise customer acquisition across financial services, fintech, and adjacent regulated industries.This role sits directly under the Head of Enterprise Sales and is designed for a seller who thrives incomplex, consultative sales environments—someone who can manage long sales...

  • Account Executive, Enterprise

    4 days ago

    Toronto, Ontario, Canada Stripe Full time

    Who we are   About Stripe   Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering...

  • Account Executive, Enterprise

    2 weeks ago

    Toronto, Ontario, Canada Stripe Full time

    Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering...

  • Enterprise Account Executive

    6 days ago

    Toronto, Ontario, Canada Armis Security Full time $140,000 - $175,000

    Armis, the cyber exposure management & security company, protects the entire attack surface and manages an organization's cyber risk exposure in real time. In a rapidly evolving, perimeter-less world, Armis ensures that organizations continuously see, protect and manage all critical assets - from the ground to the cloud. Armis secures Fortune 100, 200 and...