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. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same. 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 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.

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.

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 Hold the team to a high bar of execution while providing the clarity, structure, and hands‑on coaching needed to meet it. Scale expertise, process, and go‑to‑market effectiveness 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.

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.



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 ~ 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 ~ Experience scaling and overseeing large Field Sales teams ~ Strong ability to communicate and build relationships with senior executives ~ Block takes a market‑based approach to pay, and pay may vary depending on your location. 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. 202,000 — $304,000 CAD 202,000 — $304,000 CAD Block takes a market‑based approach to pay, and pay may vary depending on your location. 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. 180,208 — $270,312 CAD 180,208 — $270,312 CAD 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, versatile time off, retirement savings plans, and modern family planning are just some of our offering. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time.

Together, we’re helping build a financial system that is open to everyone. #

📌 Sales Manager, Field Sales (Toronto)
🏢 Block
📍 Toronto