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Field Sales Account Executive

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Block

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Location:
Canada , Kelowna

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Category:
Sales

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Contract Type:
Not provided

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Salary:

95938.00 - 143937.00 CAD / Year
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Job Description:

At Square, we're re-imagining how small and midsize businesses grow. As a Sales Account Executive on our Outbound Team, you'll bring Square's ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You'll run sophisticated, multi-product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.

Job Responsibility:

  • Own the full outbound sales cycle — from prospecting to negotiation to close — with SMB and 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 unique needs
  • Conduct high-impact discovery, demos, and negotiations with decisiveness across multi-stakeholder deals
  • Act as a consultant and trusted advisor — seamlessly flexing across BDR, AE, and AM responsibilities when needed
  • Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions
  • Maintain disciplined pipeline management and forecasting accuracy in Salesforce
  • Consistently hit and exceed revenue goals — monthly and quarterly

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 — diagnose business challenges and map tailored solutions
  • A hunter's mindset — resilient, creative, and driven to win
  • Ability to work independently while contributing to a team-first environment
  • Advanced proficiency with Salesforce and modern sales tools
What we offer:
  • Remote work
  • Medical insurance
  • Flexible time off
  • Retirement savings plans
  • Modern family planning

Additional Information:

Job Posted:
April 20, 2026

Employment Type:
Fulltime
Work Type:
Remote work
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