Canada GTM Strategy & Operations Lead

Overview

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.

The Role

As the GTM Strategy and Operations Lead for Square in Canada, you will drive the strategy, planning, and execution that fuel our growth. You will partner with Sales, Account Management, Partnerships, Marketing, Product, and Finance leadership to define priorities, build scalable go-to-market motions, and ensure disciplined execution. By combining sharp strategic thinking with operational excellence, you will help Square capture new opportunities, expand market share, and accelerate revenue in Canada.

• Drive GTM Strategy & Market Expansion
• Turn market and competitive insights into actionable go-to-market strategies that accelerate revenue and expand market share.
• Prioritize opportunities, make trade-off recommendations, and mobilize teams to capture new customer segments.
• Launch and scale repeatable playbooks across verticals, channels, and partnerships to drive sustainable growth.

• Execute High-Impact Market Programs
• Scope, lead, and own end-to-end strategic initiatives that solve high-impact business problems.
• Build business cases, align stakeholders, and deliver measurable outcomes through execution.
• Identify and activate high-value verticals, partnerships, and channels by driving cross-functional go-to-market launches.

• Partner with Finance to Co-Lead GTM Planning & Execution Rhythms
• Co-lead annual, quarterly, and long-range planning processes with Finance, ensuring alignment across Sales, Marketing, Partnerships, and Product.
• Run the rhythm of business (annual, quarterly, monthly reviews) with Finance, driving accountability to plans and surfacing course corrections quickly.
• Translate business results into clear actions that drive faster execution and better outcomes.

• Deliver Performance Insights That Drive Action
• Define KPIs in partnership with Analytics and Finance and ensure they are embedded in day-to-day decision-making.
• Track progress against goals, highlight gaps, and push teams to act decisively on insights.
• Use data to guide where to double down, pivot, or stop work, ensuring resources focus on the highest-return opportunities.

• Lead Cross-Functional Alignment & Build Scalable Systems
• Align Sales, Marketing, Partnerships, and Product teams around a unified growth vision, breaking down silos and accelerating execution.
• Serve as a trusted advisor to senior leadership, surfacing opportunities, while resolving roadblocks at pace.
• Build and operationalize scalable processes and cadences that increase clarity, speed, and impact across GTM functions.

• 8+ years of experience in Strategy, Operations, Management Consulting, or related fields; experience in SaaS, Fin Tech, or partnership ecosystems is a plus.
• Proven track record of leading strategic initiatives and cross-functional projects in high-growth environments, with strong analytical and problem-solving skills.
• Excellent communication and stakeholder management skills, with the ability to influence executive leaders and drive alignment across teams.
• Experience leading through influence and building scalable processes that drive sustainable growth.
• Bias toward action, with the ability to thrive in ambiguity, flex between strategy and execution, and drive results with minimal guidance.

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. If you require an accommodation, let your recruiter know. We are committed to an inclusive interview experience, including providing reasonable accommodations throughout the recruitment…