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[Remote] Manager, Field Sales - Central South
Note: The job is a remote job and is open to candidates in USA. Square is a technology company that builds tools to increase access to the global economy, particularly in commerce and financial services. They are seeking a senior leader for their field sales organization who will develop and manage a team of Territory Account Executives, driving sales through a disciplined and insight-led approach. The role emphasizes hands-on leadership, high-performance culture, and collaboration across the business to enhance product-market fit and revenue generation.
Responsibilities
- 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
- 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
- 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 — 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
- 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
Skills
- 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
Benefits
- Remote work
- Medical insurance
- Flexible time off
- Retirement savings plans
- Modern family planning
Company Overview
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