About the role
Block - Careers - Manager, Field Sales - Toronto Block logo News Impact AI Open Source Bitcoin Careers Builder Fellowship Investors SEE ALL JOBS ; Manager, Field Sales - Toronto Apply Remote Toronto, Ontario, Canada Req ID: R0006767 Posted yesterday Apply Job Details Apply 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 Square is building a world-class, high-accountability field sales organization — and we’re looking for a leader who is both a coach and a builder. You know the craft of selling deeply: how to open doors, generate pipeline, position value competitively, and close with precision. You lead from the front, developing your team through active engagement — not from the sidelines. You will be the driving force behind a disciplined, insight-led sales motion that blends in-person selling with proactive outbound strategy. Your leadership will elevate both the quality and velocity of revenue while shaping a culture rooted in excellence, ownership, and growth. If you are a hands-on leader with deep product expertise, strong competitive instincts, and a track record of raising the bar for sellers — this is your next move. You Will Lead with expertise in the field Develop Territory Account Executives through active, in-market coaching — from sourcing and opening conversations to consultative discovery, competitive positioning, and closing with clarity. Model world-class selling by joining prospect and customer meetings, demonstrating product fluency, value articulation, and decisive deal strategy. Spend significant time in the field with your team, strengthening local relationships, fueling community-driven pipeline creation, and ensuring sellers experience Square through a human, product-driven presence. Operate in the details Manage pipeline and KPIs with rigor — diagnosing gaps, identifying risks, expanding coverage, and guiding AEs to create and progress high-quality opportunities. Run disciplined weekly pipeline, forecast, and deal reviews that drive action, accountability, and predictable outcomes across multiple markets. Use data-backed insights to coach AE effectiveness, elevate sales execution, and ensure consistent momentum across high-velocity, complex sales cycles. Build a high-performance, high-accountability culture Create an environment defined by trust, clear expectations, ownership, and open communication. Hold