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Inside Sales Account Executive

Canada, Toronto · Job Posted May 06, 2026
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Job Description

At Square, we're re-imagining how small and midsize businesses grow. As an Inside Sales Account Executive, you'll convert high-quality inbound leads into long-term customers — while also sourcing your own opportunities to keep your pipeline full. You'll be at the heart of our growth engine: fast-paced, metrics-obsessed, and built for people who hold themselves to a higher bar than anyone else will. This is a role for people who don't wait for direction, don't make excuses, and don't settle for 'good enough'.

Job Responsibility

  • Own the full sales cycle from first conversation to close with SMB merchants
  • Engage and convert a steady flow of warm inbound leads
  • Generate a meaningful portion of your pipeline through outbound
  • Operate with urgency across every stage
  • Understand customer pain points and deliver value-based consultative solutions
  • Collaborate across teams to ensure seamless customer experience
  • Track and forecast your pipeline accurately in Salesforce
  • Consistently hit and exceed monthly and quarterly revenue goals
  • Raise your own bar every quarter
  • Turn obstacles into momentum

Requirements

  • 1-2 years of inside sales or full-cycle closing experience, ideally in a fast-paced SaaS, payments, or SMB-focused environment
  • Proven ability to exceed quota and close business in a high-volume, short-cycle motion
  • Strong phone, video, and written communication skills
  • A true hunter mentality
  • Curiosity and empathy: dig into the customer's business, uncover real needs, and position the right solution with confidence
  • Ability to thrive in ambiguity
  • CRM fluency (Salesforce or similar) and a data-driven approach to activity management
  • High standards for yourself and your team

What we offer

  • Remote work
  • medical insurance
  • flexible time off
  • retirement savings plans
  • modern family planning
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