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About the Role

Square is building a world-class, high-accountability field sales organization and is looking for a leader who is both a coach and a builder. 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.

Responsibilities

Lead with expertise in the field
Develop Territory Account Executives through active, in-market coaching
Model world-class selling by joining prospect and customer meetings
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
Run disciplined weekly pipeline, forecast, and deal reviews
Use data-backed insights to coach AE effectiveness, elevate sales execution, and ensure consistent momentum across high-velocity, complex sales cycles
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
Become a product and competitive expert
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

Requirements

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

Experience Level

8+ years of sales success
5+ years of leadership experience

Salary/Compensations

$202,000—$304,000 CAD

Benefits

Remote work
Medical insurance
Flexible time off
Retirement savings plans
Modern family planning

About the Company

Square makes commerce and financial services accessible to sellers.
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Together, we’re helping build a financial system that is open to everyone.