SMB Account Executive, Canada

📋 Description

• Own the full outbound sales cycle from prospecting to close for mid-market merchants.
• Build and manage a high-quality pipeline through cold outreach and targeted campaigns.
• Develop multi-product solutions across Square’s ecosystem for each merchant.
• Partner with Business Development on lead flow while driving net-new logo acquisition.
• Conduct discovery, demos, and negotiations across multi-stakeholder deals.
• Act as a consultant and trusted advisor, collaborating with cross-functional teams.

🎯 Requirements

• 5+ years of full-cycle B2B sales experience with quota achievement.
• Proven outbound prospecting success 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 outreach.
• Exceptional communication, presentation, and negotiation skills across channels.
• Strong consultative selling skills and hunter mindset; able to work independently.

🎁 Benefits

• Remote work; medical insurance; flexible time off; retirement savings plans; modern family planning.
• Inclusive workplace with equal opportunity commitments and accommodations.