Senior Account Executive, Mid-Market Ontario

Senior Account Executive, Mid-Market - Canada

Remote Toronto, Ontario, Canada Req : R0006753 Posted yesterday

At Square, we’re re‑imagining how mid‑market businesses grow. As a Senior Sales Account Executive on our Mid‑Market Team, 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.

If you’re an experienced closer who thrives in outbound environments, loves solving meaningful business challenges, and consistently delivers against ambitious targets — this is your role.

• 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.

• 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
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• Ability to sell in both French and English.

Block takes a market‑based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job‑related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

OTE for this role is: $152,300 - $228,500 CAD

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.