Senior Account Executive, Mid-Market

Responsibilities

• Own the full outbound sales cycle—from prospecting and negotiation through 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 to deliver cohesive solutions.
• Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
• Consistently 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 experience 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 and the ability to map tailored solutions to business challenges.
• Resilient, creative, and driven approach to winning business.
• 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.
• Ability to sell in both French and English.

Compensation and Benefits

• OTE: $152,300–$228,500 CAD.
• Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning benefits.