Head of Canada Sales

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 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.
The Role
Square's mission is to empower businesses of all sizes to start, run, and grow. As we continue to strengthen our presence in Canada, we're seeking an experienced, strategic, and people-focused sales leader to serve as Head of Canada Sales for our SMB and Mid-Market segments.
In this role, you will join Square's GlobalSales leadership team, shaping how we go to market across Canada's key business segments. You'll collaborate cross-functionally to drive revenue growth, expand market share, and build a scalable sales organization that consistently exceeds targets. You will report to the Global Head of Sales for Square.
You Will

• Develop and lead the sales strategy for Canada, defining goals, operating plans, and success metrics across SMB and Mid-Market segments.
• Oversee and support a multi-layered team of Sales Managers and Account Executives, ensuring effective leadership, coaching, and execution across all levels.
• Drive consistent performance and accountability, ensuring strong pipeline health, quota attainment, and revenue delivery.
• Attract, develop, and retain diverse talent, building an inclusive and high-engagement culture grounded in collaboration and shared success.
• Implement scalable processes and operating rhythms that make performance measurable, repeatable, and sustainable.
• Collaborate cross-functionally with Marketing, Product, Finance, Sales Operations, and Customer Success to align strategies and remove obstacles to growth.
• Partner with Sales Operations and Finance to enhance forecasting accuracy, compensation design, and resource allocation.
• Refine and expand inbound and outbound sales motions, leveraging insights and data to continuously improve productivity and effectiveness.
• Represent the voice of customers and field teams, sharing insights that inform product direction and go-to-market strategy.
• Model Square's values and culture, fostering inclusion, transparency, and integrity.

You Have

• 8+ years of B2B sales experience within technology or financial services, with a strong record of meeting or exceeding targets.
• 3+ years of leadership experience managing multi-layered teams, including both Sales Managers and Account Executives.
• Proven success in developing and executing sales strategies that drive measurable growth and customer impact.
• Experience building and scaling sales processes that enable consistent execution in a high-growth environments.
• Strong commercial and analytical skills, with the ability to set meaningful KPIs, analyze performance, and act decisively.
• Demonstrated cross-functional influence, aligning stakeholders across Product, Marketing, Finance, and Operations toward shared outcomes.
• A balanced leadership style that combines strategic vision, operational discipline, and empathy.
• A deep commitment to supporting Canadian SMB and Mid-Market businesses and advancing Square's mission to help them grow.

Why You'll Love Working Here

• Impact: You'll shape the future of Square in one of our most exciting and strategic growth markets, directly influencing how we serve Canadian businesses.
• Growth: You'll operate in a fast-paced, high-growth environment with significant opportunity to scale the business, develop new sales motions, and hone your leadership.
• Culture: You'll join a diverse, inclusive, and mission-driven team that values bold ideas, transparency, and continuous learning-where your contributions will make a tangible difference to our sellers and our business.

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 also consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations throughout the recruitment process. If you require an accommodation, let your recruiter know. Want to learn more about what we're doing to build an inclusive workplace? Check out our Inclusion & Diversity page .
Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two 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.
Zone A:
$207,686 - $311,564 CAD
Zone B:
$207,686 - $311,564 CAD
Use of AI in Our Hiring Process
We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.
Contact us at [email protected] with hiring practice or data usage questions.
Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.
Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we're helping build a financial system that is open to everyone.