Mid-Market Account Executive

Square · Toronto, Ontario · $152,320 - $228,480 CAD 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