Manager, Field Sales

Responsibilities

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.
• Model effective selling by joining prospect and customer meetings, demonstrating product fluency, value articulation, and deal strategy.
• Spend significant time in the field with the team, strengthening local relationships and creating community-driven pipeline.

Operate in the details

• Manage pipeline and KPIs by diagnosing gaps, identifying risks, expanding coverage, and guiding Account Executives to create and progress high-quality opportunities.
• Run weekly pipeline, forecast, and deal reviews that drive action, accountability, and predictable outcomes across multiple markets.
• Use data-backed insights to coach Account Executive effectiveness and elevate sales execution.

Build a high-performance culture

• Create an environment defined by trust, clear expectations, ownership, and open communication.
• Hold the team to a high execution standard while providing clarity, structure, and hands-on coaching.
• Hire, onboard, and develop Account Executives to ramp quickly, deepen product expertise, and exceed quota.

Scale sales effectiveness

• Become a product and competitive expert so the team can articulate Square’s value and differentiation.
• Build scalable, repeatable field sales motions that increase funnel quality, improve outbound productivity, and accelerate growth.
• Refine strategy, playbooks, and operating rhythms to deepen Square’s presence and win market share across local ecosystems.

Partner across the business

• Champion the customer voice and collaborate cross-functionally to strengthen product-market fit and unlock new revenue pathways.
• Engage 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.
• Bias toward action and experimentation, balanced with thoughtful decision-making.
• 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 sales teams, preferably field sales.
• Strong ability to communicate and build relationships with senior executives.
• Excellent interpersonal, leadership, organizational, and communication skills.

Benefits

• Remote work options.
• Medical insurance.
• Flexible time off.
• Retirement savings plans.
• Modern family planning benefits.