Senior Sales Manager - Mid-Market

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

We’re building a team of elite sales leaders who raise the performance of everyone around them.

As a Senior Sales Manager, you'll lead a team of approximately 10 Senior Account Executives while owning one of our most important growth levers: developing talent that consistently outperforms expectations. This role isn't about managing activity, it's about building a high-performance sales organization where every hire strengthens the team, every coaching conversation improves execution, and every business decision is grounded in data.

You'll lead our most experienced Account Executives, AEs with 5+ years of full-cycle closing experience, on a fully outbound team where pipeline is strategic and self-sourced across executive networks, partnerships, trade shows, intent data, and more. Your reps own the execution. You sharpen the strategy behind it, and you coach in the work rather than after it. That means diagnosing pipeline health before it becomes a forecasting problem, developing future leaders before promotions become necessary, and building playbooks and an operating rhythm that makes growth predictable.

You'll partner cross-functionally to improve how we sell, challenge the status quo, and continuously raise the talent bar across the organization. Success is measured not only by quota attainment, but by the strength of your team, the quality of your pipeline, and the leaders you develop.

You Will

• Build a High-Performance Team
• Hire exceptional Account Executives and raise the talent bar with every addition to your team. 
• Develop a culture of ownership, accountability, continuous learning and high standards. 
• Identify future top performers early and create development plans that accelerate their growth. 
• Coach Through Data & Business Intelligence
• Lead your business through rigorous pipeline inspection, forecasting and performance diagnostics. 
• Use leading indicators to identify performance gaps early and coach reps toward sustainable improvement. 
• Turn data into action by identifying trends, diagnosing root causes and driving measurable improvements across your team. 
• Drive Operational Excellence 
• Establish predictable operating rhythms around forecasting, pipeline management and business reviews. 
• Build disciplined education that creates consistent, repeatable revenue outcomes. 
• Continuously improve how your team sells by refining processes, simplifying execution and eliminating friction. 
• Lead Through Influence 
• Partner closing with sales Leadership, Marketing, Enablement, Operations and Product to improve the customer journey and strengthen commercial execution. 
• Use customer insights and field intelligence to shape strategy and influence product evolution. 
• Lead through change by helping your team adapt quickly while maintaining high performance. 

You Have

• 7+ years experience as a sales manager. 
• 3 years of documented sales success as an individual contributor exceeding target. 
• A proven track record leading high-performing sales teams in a fast-paced, high-growth environment.
• Experience leading an outbound-led team, with the ability to coach outbound as a strategy: ICP targeting, multi-channel approach, and pipeline quality over sheer volume, rather than as an activity metric.
• Success developing Account Executives into top performers through structured coaching and clear performance expectations.
• Deep expertise in pipeline management, forecasting, and using data to improve business outcomes.
• Demonstrated experience hiring exceptional talent and building teams that consistently outperform.
• Strong business judgment with the ability to balance short-term execution and long-term organizational health.

Zone A: 171640 - 257460 CAD
Zone B: 171640 - 257460 CAD