Role Description
Square is building a world-class, high-accountability field sales organization β and weβre looking for a leader based in North Carolina who is both a coach and a builder. You know the craft of selling deeply: how to open doors, generate pipeline, position value competitively, and close with precision. You lead from the front, developing your team through active engagement β not from the sidelines.
You will be the driving force behind a disciplined, insight-led sales motion that blends in-person selling with proactive outbound strategy. Your leadership will elevate both the quality and velocity of revenue while shaping a culture rooted in excellence, ownership, and growth.
If you are a hands-on leader with deep product expertise, strong competitive instincts, and a track record of raising the bar for sellers β this is your next move.
-
Lead with expertise in the field
-
Develop Territory Account Executives through active, in-market coaching β 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 β 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 β ensuring your team can confidently articulate Squareβs 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 Squareβs 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.
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
-
Excellent interpersonal, leadership, organizational, and communication skills
Benefits
-
Remote work
-
Medical insurance
-
Flexible time off
-
Retirement savings plans
-
Modern family planning
Company Description
Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people.
-
Square makes commerce and financial services accessible to sellers.
-
Cash App is the easy way to spend, send, and store money.
-
Afterpay is transforming the way customers manage their spending over time.
-
TIDAL is a music platform that empowers artists to thrive as entrepreneurs.
-
Bitkey is a simple self-custody wallet built for bitcoin.
-
Proto is a suite of bitcoin mining products and services.
Together, weβre helping build a financial system that is open to everyone.