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Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together.
So we expanded into software and started building integrated, omnichannel solutions - to help sellers sell online, manage inventory, offer buy now, pay later functionality,  book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.
Today, we are a partner to sellers of all sizes - large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

Preferred locations: Greater Vancouver, Calgary, Toronto, Montreal areas

The Role

The Account Management organization is seeking a results-driven and people-focused leader to manage a team of SMB Account Managers. In this role, you will lead growth and retention efforts across a portfolio of Square's SMB  merchants, ensuring your team delivers consistent, high-quality customer engagement and measurable business outcomes. You will report directly to the Head of Account Management for Canada.

As a team leader, you will oversee a high-performing group of 8-10 Account Managers, driving results in revenue expansion, software adoption, and churn reduction. You'll foster a data-driven, mission-aligned culture while prioritizing coaching and team development.

This is a cross-functional role where you will partner closely with Product, Operations, and Sales to ensure strong execution, share merchant feedback, and support our mission of Economic Empowerment. 

You Will:

• Lead and develop a remote team of 8-10 Account Managers focused on growth and retention for SMB merchants.
• Drive measurable outcomes in upsell, retention, and customer satisfaction through strong pipeline management and consistent coaching
• Establish clear performance expectations and accountability through structured 1:1s, deal reviews, and team cadences.
• Partner cross-functionally to surface merchant insights, resolve escalations, and improve the overall customer experience.
• Support leadership in executing team OKRs and implementing program improvements.
• Identify enablement opportunities and reinforce best practices across the team.
• Serve as a senior escalation point for complex or high-impact merchant situations.
• Travel approximately once per quarter for team events or customer meetings.

You Have:

• 8-10+ years of experience in Account Management, Sales, Business Development, or Marketing
• 3-5 years of direct people management experience in a quota-carrying or performance-driven environment.
• Experience working with SMB or Mid-Market businesses.
• A track record of consistently exceeding revenue and retention goals.
• Strong coaching skills with demonstrated ability to improve performance across a team.
• Experience working cross-functionally to resolve issues and improve processes.
• Excellent written and verbal communication skills.
• Bilingual EN/FR ideal

We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances.
We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build a workplace that is fair and square? Check out our I+D page.

Pay Transparency:

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four 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. To find a location's zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information.

Zone A: (167,500 CAD - 251,300 CAD)

Zone B: (167,500 CAD - 251,300 CAD)