Manager, SMB Account Management

About the Company

Since its founding in 2009, Square has significantly advanced the commerce landscape by evolving from a payment facilitator to a provider of integrated omnichannel solutions. The company offers sellers a comprehensive suite of tools including online sales platforms, inventory management, buy now pay later options, appointment bookings, customer engagement features, and staffing/payroll solutions. Financial services such as business loans and cash flow management are integrated at the point of sale. Through its brand Afterpay, Square enables merchants to access next-generation shoppers and scale their businesses.

Square supports merchants ranging from startups to large enterprises with complex operations. As customers grow, Square continuously enhances its solutions to foster their success. The company has notable opportunities especially in Canadian markets including Greater Vancouver, Calgary, Toronto, and Montreal.

Role Overview

The Account Management division is recruiting a driven and people-oriented leader to oversee a remote team of 8–10 SMB Account Managers. This role focuses on growing revenue, expanding software adoption, and reducing customer churn within the SMB merchant portfolio. Reporting to the Head of Account Management for Canada, the manager will cultivate a data-informed, mission-centered culture emphasizing coaching and development.

This position requires cross-functional collaboration with Product, Operations, and Sales teams to ensure excellent execution, share merchant feedback, and uphold Square’s mission of Economic Empowerment.

Key Responsibilities

• Lead and develop a remote team of 8–10 Account Managers responsible for retention and growth of SMB merchants.
• Manage pipelines to drive increased upsell, improved retention, and elevated customer satisfaction through continuous coaching and feedback.
• Set clear performance targets and accountability via regular one-on-ones, deal evaluations, and consistent team meetings.
• Collaborate with other departments to identify merchant insights, tackle escalations, and enhance overall customer experience.
• Support company leadership in achieving team objectives and refining programs.
• Identify training needs and promote adoption of best practices across the team.
• Act as senior escalation contact for complex or critical merchant issues.
• Occasional quarterly travel for team gatherings or customer engagements.

Qualifications

• 8 to 10+ years in Account Management, Sales, Business Development, or Marketing.
• 3 to 5 years managing teams in quota-driven environments.
• Experience supporting SMB or Mid-Market businesses.
• Proven history of exceeding revenue and retention targets.
• Strong coaching skills with measurable impact on team performance.
• Cross-functional collaboration experience enhancing processes and resolving challenges.
• Excellent written and verbal communication abilities.
• Bilingual proficiency in English and French is preferred.

Additional Information

Square is committed to creating an inclusive environment that gives equal opportunity to all applicants, including those with arrest or conviction records, following applicable laws. The company ensures a fair hiring process and accommodates applicants with disabilities confidentially.

Compensation is market-based and varies by location within Canada, with salary bands ranging approximately from CAD 167,500 to CAD 251,300 annually.

Application limits allow up to 9 active submissions within 60 days, with a 90-day waiting period before reapplying to the same role post review.

Automated AI tools may be used during application evaluations to promote fairness and compliance with local regulations.

Benefits

Square offers various benefits designed to empower employees, including remote work capabilities, health insurance, flexible time off, retirement plans, and support for family planning. Further benefit details can be found through the company’s internal resources.

Company Brands

Square is part of Block, Inc., which also encompasses Cash App, Afterpay, TIDAL, Bitkey, and Proto, collectively working towards an inclusive financial ecosystem.

Privacy

The company adheres to strict data privacy regulations.