Top Sales Jobs in Toronto, ON

Manage and grow a book of SMB merchant accounts in Eastern Canada by identifying upsell opportunities, educating customers on Square products, resolving issues, collaborating with Sales/Support/Product teams, and improving the managed accounts program to drive retention and revenue.

The Account Executive will introduce Square's ecosystem to SMB merchants, oversee the sales cycle, achieve sales goals, and collaborate with teams to meet market needs.

The Business Development Rep Associate will initiate contact with potential sellers, promote Square's services, and document opportunities for the Account Executive team, while developing sales skills and advancing within the company.

The Enterprise Account Executive will manage high-value sales cycles, craft deal strategies, and lead multi-stakeholder engagements while promoting Square's solutions to enterprise clients.

Field-driven full-cycle sales role responsible for building pipeline, conducting in-person demos, closing deals, and establishing Square as the local payments and commerce partner. Requires territory presence, high-velocity outreach, partnership development, Salesforce pipeline management, and consistent quota overperformance.

Lead and coach a remote team of Account Executives to hit individual and team quota. Hire, train, forecast, manage pipeline and KPIs, run regular reviews, participate in client meetings, refine sales strategy, and use customer feedback to improve products and processes.

Lead and develop a remote mid-market sales team of Account Executives to drive revenue. Hire, train, and coach AEs; enforce KPI-driven execution, forecasting, and pipeline management; run pipeline and forecast reviews; evolve sales strategy and processes; participate in client/prospect meetings and use customer feedback to improve products.

Manage and scale outbound sales development team, shape strategy, improve pipeline generation, coach BDRs, ensure cross-functional alignment, and optimize performance.

Lead and close high-value, complex enterprise deals end-to-end. Drive insight-led strategy, manage multi-stakeholder technical sales cycles with Solutions Engineering, align internal stakeholders (Finance, Legal, Risk, Product), represent the company to executives, influence product and GTM, and use AI tools to increase efficiency.

The Strategic Account Manager will drive growth and retention within retail accounts, serving as a trusted advisor, implementing tailored solutions, and collaborating with cross-functional teams to enhance performance and satisfaction.