Field Sales Manager, North Carolina

Square; Raleigh (NC); On-site; USD 174,000 - 261,000; Full time

Job summary

Square is seeking an experienced sales leader to guide Territory Account Executives, model in-market selling, and drive a human, product-driven presence. You will spend substantial time in the field with your team, strengthening relationships and fueling community-driven pipeline creation.

Responsibilities include rigorous pipeline management, weekly forecasts, data-driven coaching, and building scalable field motions to accelerate growth across multiple markets while maintaining a

Qualifications

• 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.

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

Sales leadership

Leadership experience

SaaS / financial services sales

Bias toward action

Executive communication

Cross-functional collaboration

Metrics-driven

Field sales scaling

People management

Interpersonal skills

Job description

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

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to identity or other legally protected class. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future. To find a location's zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information.

Zone A: ($198,000 - $297,000)

Zone B: ($184,000 - $276,000)

Zone C: ($174,000 - $261,000)

Zone D: ($164,000 - 246,000)

Amounts listed above include target variable compensation.