Mid-Market Account Executive

Posted 13 hours ago

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About the role

  • Mid-Market Account Executive selling Square’s integrated commerce and financial services solutions to merchants. Building outbound pipelines and closing complex, multi-product B2B deals.

Responsibilities

  • Own the full outbound sales cycle from prospecting to negotiation to close with mid-market merchants
  • Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies
  • Develop multi-product solutions across Square’s ecosystem and tailor them to each merchant’s needs
  • Partner with Business Development on lead flow while independently driving net-new logo acquisition
  • Conduct discovery, demos, and negotiations across multi-stakeholder deals
  • Act as a consultant and trusted advisor, flexing across BDR, AE, and AM responsibilities when needed
  • Collaborate with Product, Marketing, Implementation, and Operations
  • Maintain pipeline management and forecasting accuracy in Salesforce
  • Hit and exceed monthly and quarterly revenue goals

Requirements

  • 3+ years of full-cycle B2B sales experience with consistent quota achievement
  • Proven success in outbound prospecting and net-new business creation; SaaS or fintech preferred
  • Experience closing complex, multi-threaded deals with longer sales cycles
  • Ability to build pipeline from scratch using targeted, strategic outreach
  • Exceptional communication, presentation, and negotiation skills across phone, video, and written channels
  • Strong consultative selling skills
  • Ability to work independently while contributing to a team-first environment
  • Advanced proficiency with Salesforce and modern sales tools
  • BA/BS degree or equivalent experience

Benefits

  • Remote work
  • Medical insurance
  • Flexible time off
  • Retirement savings plans
  • Modern family planning
  • Reasonable accommodations throughout the recruitment process

Job type

Full Time

Experience level

Mid levelSenior

Salary

CA$116,064 - CA$174,096 per year

Degree requirement

Bachelor's Degree

Location requirements

RemoteCanada

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