Territory Account Executive, Mississauga

Block Block · Fintech · ON - Toronto, CA · 20249 S&M - Sales - Square Field Sales

Territory Account Executive for Square (Block) in Mississauga, ON, responsible for leading a market, building pipeline from the ground up, and closing deals for Square's full product suite of software and hardware, with a focus on restaurants, retail, and services verticals. This is a field-driven, execution-focused role requiring significant in-person client engagement and sales activities.

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

Nice to have

  • Territory Account Executive experience

What the JD emphasized

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