Territory Account Executive, Hamilton

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

This is a field sales role for a Territory Account Executive at Square (Block), focusing on selling their integrated omnichannel software and hardware solutions to businesses. The role involves building pipeline from scratch, conducting in-person demos, closing deals, and establishing strong relationships with local sellers. It requires significant time spent in the field, driving business visits, 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. Consistently exceed quota within a culture where high standards are the norm.

Skills

Required

  • 3+ years of sales experience in a full cycle closing role
  • field sales experience
  • exceeding sales targets
  • selling a diverse ecosystem of products
  • 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
  • live in the market you are serving
  • collaborative and team player mentality
  • Salesforce experience or equivalent

What the JD emphasized

  • field sales experience
  • exceeding sales targets
  • closing complex deals
  • drive deals independently
  • business development experience
  • door-to-door outreach