Territory Account Executive - Toronto

Block Block · Fintech · ON - Toronto, CA · Remote · 20213 S&M - Sales - Square Outside

Territory Account Executive for Square (Block) in Toronto, focusing on selling integrated software and hardware solutions to local businesses. This role involves significant field sales, pipeline generation, and achieving sales targets within the fintech domain.

What you'd actually do

  1. Spend ~80% of your week in the field — walking your territory, engaging local businesses, and driving 50–60 targeted business visits each week.
  2. Run a full-cycle, self-sourced sales motion: generate leads, identify needs, deliver compelling demos, and close deals across Square’s full product suite.
  3. Build strong, trust-based relationships with local sellers by being present, reliable, and value-driven.
  4. Develop a repeatable top-of-funnel engine through door-to-door outreach, community engagement, events, networking, and targeted partnerships.
  5. Build deep expertise in key verticals — including restaurants, retail, and services — to diagnose challenges and position the right Square solutions.

Skills

Required

  • 3+ years of sales experience in a full cycle closing role with field sales experience
  • Experience exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals
  • Ability to drive deals independently in a fast-paced, dynamic environment
  • Business development experience (e.g. hunting and cold calling)
  • Reliable transportation and live in the market you are serving
  • Collaborative and team player mentality
  • Prior Salesforce experience or equivalent

What the JD emphasized

  • must have reliable transportation and live in the market you are serving