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AI Fintech Startup: Account Executive

Job in Toronto, Ontario, C6A, Canada
Listing for: StackedSP Inc
Full Time position
Listed on 2026-01-02
Job specializations:
  • Business
    Business Development
  • Sales
    Business Development, Sales Development Rep/SDR, B2B Sales
Salary/Wage Range or Industry Benchmark: 252986.4 - 309205.6 CAD Yearly CAD 252986.40 309205.60 YEAR
Job Description & How to Apply Below

About the Company

Company Size: < 25 People

Industry: Fintech, AI, Software

Founding Year: 2021

Stage:
Seed

Funding: ~$20M

Investors:
Backed by top VC funds including OpenAI, Google Ventures, and General Catalyst

We’re working with a fast-growing fintech startup that’s redefining how small businesses manage finances. Their AI-driven platform replaces outdated bookkeeping tools with automation, making financial management effortless.

What you’ll do:
  • Own the entire sales cycle, from prospecting to closing, at a high-growth AI fintech.
  • Work directly with leadership to build and refine the go-to-market strategy.
  • Engage with SMBs, helping them streamline financial operations with AI-powered automation.
  • Evolve with the company—today’s motion is high-velocity and transactional, but as they scale, opportunities for more complex, strategic deals will emerge.
  • Leverage data and insights to improve sales processes and drive customer success.
What you’ll need:
  • 3-8 years of sales experience, ideally in fintech, SaaS, or a high-growth startup environment.
  • Proactive and adaptable—you thrive in fast-paced, dynamic environments.
  • Strong track record of exceeding sales targets and building lasting customer relationships.
  • Comfortable with ambiguity and excited by the challenge of refining a high-growth sales motion.
  • Passionate about AI, fintech, and transforming how businesses manage their finances.
Why Join?
  • Elite Backing – A company funded by top investors, including OpenAI and Google Ventures.
  • Early Impact – Join a team of < 25 people and play a critical role in shaping the future of the company.
  • Growth & Mobility – As the company scales, so will opportunities—whether in leadership, partnerships, or larger deal structures.
  • Culture & Perks – Regular travel to San Francisco, with a hybrid schedule at the Toronto office (4 days per week on-site)
  • Competitive Comp - 50/50 plan with competitive salary, benefits, and early-stage equity.

$180,000 - $220,000 a year

Salary Range above is salary + commission on a 50/50 plan, with opportunity to exceed. You'll also receive meaningful equity in an early stage venture backed startup commensurate with experience.

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