Senior Manager, Field Sales

The Role

Square is building a world-class, high-accountability field sales organization. As a senior leader, you will coach and develop Territory Account Executives, model world-class selling, spend significant time in the field, manage pipeline and KPIs rigorously, build a high-performance culture, scale sales processes, and partner cross-functionally.

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.

Operate in the details

• 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

• 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.

Scale expertise, process, and go-to-market effectiveness

• Become a product and competitive expert — ensuring your team can confidently articulate Square’s value and differentiation.
• 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.

Partner and innovate across the business

• 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.

You have

• 10+ years of sales success, ideally in a high-growth environment
• 8+ 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

Pay Transparency Pay varies by location zone:

• Zone A: $239,000 - $359,000
• Zone B: $222,000 - $334,000
• Zone C: $210,000 - $316,000
• Zone D: $203,000 - $305,000 Amounts include target variable compensation.