Manager, Field Sales - Toronto

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 the team to a high bar of execution while providing the clarity, structure, and hands-on coaching needed to meet it.
  • Hire, onboard, and develop AEs to ramp quickly, deepen product expertise, and consistently exceed quota.
  Scale expertise, process, and go-to-market effectiveness
  • Become a product and competitive expert — ensuring your team can confidently articulate Square’s value and differentiation.
  • Build scalable, repeatable field sales motions that increase funnel quality, improve outbound productivity, and accelerate growth in your assigned cities.
  • Continuously refine strategy, playbooks, and operating rhythms to deepen Square’s presence and win market share across key local ecosystems.
  Partner and innovate across the business
  • Champion the customer voice and collaborate cross-functionally to strengthen product-market fit and unlock new revenue pathways.
  •  Engage deeply with community networks, partners, and local events to amplify brand awareness and fuel top-of-funnel opportunity creation.

You Have

• 8+ years of sales success, ideally in a high-growth environment
• 5+ years of leadership experience, preferably managing field account executives
• Experience in high-transaction SaaS or financial services sales
• Strong bias toward action and experimentation, balanced with thoughtful decision-making
• A track record of building a winning, high-performing culture through hands-on leadership and coaching
• Extensive experience operating in a metrics-driven sales organization
• Proven ability to influence and collaborate with cross-functional partners in a rapidly scaling business
• Experience scaling and overseeing large Field Sales teams
• Strong ability to communicate and build relationships with senior executives
• Excellent interpersonal, leadership, organizational, and communication skills

Application Guidelines

Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.

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 here 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.