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Senior Account Executive, Mid-Market

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. Own the full outbound sales cycle from prospecting to negotiation to close with mid-market merchants .

Posted 11/4/2026full-timeRemote • CanadaSenior💰 CA$116,064 - CA$174,096 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in full-cycle B2B sales, including outbound prospecting, negotiation, and closing complex deals. Proficient in pipeline management and leveraging Salesforce to achieve revenue goals while collaborating cross-functionally.

Highest-signal resume keywords
Full-Cycle B2B Sales ExperienceOutbound ProspectingComplex Deal ClosingSalesforce ProficiencyConsultative Selling Skills

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
B2B SalesOutbound ProspectingPipeline ManagementNegotiationSales ForecastingMulti-Product SolutionsSaaS SalesFintech SalesTargeted OutreachRevenue Achievement
Soft Skills
Exceptional CommunicationPresentation SkillsNegotiation SkillsResilienceCreativity
Tools & Technologies
SalesforceModern Sales Tools
Certifications & Qualifications
BA/BS Degree
Industry Keywords
Outbound Sales CycleMid-Market MerchantsNet-New Logo AcquisitionCross-Functional CollaborationConsultant and Trusted Advisor

About the role

Key responsibilities & impact
  • 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 cross-functionally with Product, Marketing, Implementation, and Operations
  • Maintain pipeline management and forecasting accuracy in Salesforce
  • Consistently hit and exceed monthly and quarterly revenue goals

Requirements

What you’ll need
  • 5+ 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
  • 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
  • BA/BS degree or equivalent experience

Benefits

Comp & perks
  • Remote work
  • Medical insurance
  • Flexible time off
  • Retirement savings plans
  • Modern family planning
  • Reasonable accommodations for disabled applicants throughout the recruitment process