Mid-Market Account Executive

As a Mid-Market Account Executive at Square, 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.

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 unique needs.
• Partner with Business Development on lead flow while independently driving net-new logo acquisition.
• 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.
• BA/BS degree or equivalent experience

Benefits:

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

OTE for this role is: $152,320 - $228,480 CAD