Sales Manager, Mid-Market

The Sales Manager, Mid-Market at Square (Block) is a leadership role focused on driving growth within the mid-market segment. This position involves leading a team of approximately 10 Senior Account Executives, each with over five years of full-cycle closing experience. The role is remote, based in Toronto, Ontario, Canada.

Key responsibilities include building and managing a high-performance sales team, coaching through data and business intelligence, driving operational excellence, and leading through influence. The Sales Manager will hire exceptional Account Executives, develop a culture of ownership and continuous learning, and establish predictable operating rhythms around forecasting and pipeline management. Collaboration with sales leadership, marketing, enablement, operations, and product teams is essential to improve the customer journey and strengthen commercial execution.

Candidates should have at least seven years of experience as a sales manager, with a proven track record of leading high-performing sales teams in fast-paced, high-growth environments. A minimum of three years of documented sales success as an individual contributor exceeding targets is required. Experience leading an outbound-led team, with the ability to coach outbound strategies such as ideal customer profile targeting and multi-channel approaches, is essential.

While specific compensation details are not provided, Square (Block) offers a comprehensive benefits package, including health and wellness programs, professional development opportunities, and a collaborative work environment. The company is committed to fostering a culture of inclusion and continuous learning.

Square (Block) is a global company dedicated to building simple, powerful tools that make progress towards an economy that’s truly open to all. The company offers opportunities for growth and development, encouraging employees to build and innovate within a supportive and dynamic environment.