Head of SMB Account Management, Canada

  • Full-time

Company Description

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 through Afterpay, 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.

Job Description

Square Canada is looking for a passionate innovative go to market leader to grow and manage our Canadian based Account Management Team (inside sales) and join a cross-functional leadership team in driving Square’s market share in Canada. You will be responsible for planning, organizing, energizing and leading a group of direct Account Managers and eventually leaders. Your impact in this role will directly influence Square’s market expansion strategy and the retention and growth of Square’s upmarket businesses (small to medium size businesses) in the region. Your experience will be a valuable contribution to Square’s approach in preserving and improving the Merchant experience, nurturing a culture of growth mindset, and investing in individual team members development. This role reports directly to our Global Head of SMB Account Management. 

You will:

  • Be a key driving force in continuing Square’s Account Management team growth, specifically in our SMB segment
  • Create a vision for the Canada Account Management Team alongside our Global SMB AM vision with the goal of growing your team alongside Square’s continued success in Canada 
  • Partner cross-functionally with Finance, Sales, Marketing and Senior Leadership globally to shape Square go to market strategy in Canada 
  • Act as a key contributor to our Global Account Management Leadership team 
  • Drive improvements through pilots and experimentation to the AM and Merchant experience through close partnership with data science, automation, tooling and analytics partners 
  • Own experimentation within the existing Merchant portfolio to unlock new and expanded AM opportunities 
  • Act as a leader and decision maker in goal setting, AM incentive structures, and establishing performance levers
  • Bring a creative, seller obsessed and collaborative mindset to the work you do each day 


  • 7-10 years of sales or account management success, preferably in a high growth company
  • Passion for supporting, growing, and empowering SMB/Mid-Market businesses
  • Love for developing people at all stages of their career and leading organizations through change
  • 6+ years of leadership experience, with experience leading distributed teams of managers and individual sales people 
  • Proven ability to work with and influence cross-functional teams and departments in a rapidly growing environment
  • Understanding of Square’s culture and mission
  • Proven ability to communicate (written and verbal) with senior executives
  • Excellent interpersonal, leadership, organizational, and communication skills
  • Extensive experience in a metrics-driven sales organization
  • (Preferred) Experience in financial services or SaaS sales 
  • (Preferred) Fluency in French 

Additional Information

US and Canada EEOC Statement

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 a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. 

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.

Additionally, we consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.



We want you to be well and thrive. Our global benefits package includes:

  • Healthcare coverage
  • Retirement Plans
  • Employee Stock Purchase Program
  • Wellness perks
  • Paid parental leave
  • Paid time off
  • Learning and Development resources

Block, Inc. (NYSE: SQ) is a global technology company with a focus on financial services. Made up of Square, Cash App, Spiral, TIDAL, and TBD, we build tools to help more people access the economy. Square helps sellers run and grow their businesses with its integrated ecosystem of commerce solutions, business software, and banking services. With Cash App, anyone can easily send, spend, or invest their money in stocks or Bitcoin. Spiral (formerly Square Crypto) builds and funds free, open-source Bitcoin projects. Artists use TIDAL to help them succeed as entrepreneurs and connect more deeply with fans. TBD is building an open developer platform to make it easier to access Bitcoin and other blockchain technologies without having to go through an institution.

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