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. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

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 robust execution, share merchant feedback, and support our mission of Economic Empowerment.

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. Serve as a senior escalation point for complex or high-impact merchant situations. Travel approximately once per quarter for team events or customer meetings. 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. ~ Strong coaching skills with demonstrated ability to improve performance across a team. ~ 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.

We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Block takes a market-based approach to pay, and pay may vary depending on your location.

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.

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

📌 IMMEDIATE ACCOUNT MANAGERS NEEDED!!! (Vancouver)
🏢 Block
📍 Vancouver