Manager, Field Sales

You will:
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:
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

Skills Required
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
Proven ability to scale and oversee large Field Sales teams
Extensive experience operating in a metrics-driven sales organization
Track record of building a high-performing culture through hands-on leadership and coaching
Strong ability to communicate and build relationships with senior executives
Proven ability to influence and collaborate with cross-functional partners
Excellent interpersonal, leadership, organizational, and communication skills