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About the Role

Square is building a world-class, high-accountability field sales organization and is looking for a leader who is both a coach and a builder. 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.

Responsibilities

Lead with expertise in the field
Develop Territory Account Executives through active, in-market coaching
Model world-class selling by joining prospect and customer meetings
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
Run disciplined weekly pipeline, forecast, and deal reviews
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
Ensure your team can confidently articulate Square’s value and differentiation

Requirements

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

Skills

Deep knowledge of the craft of selling: how to open doors, generate pipeline, position value competitively, and close with precision
Hands-on leadership
Deep product expertise
Strong competitive instincts
Active engagement leadership style
Disciplined sales motion
In-person selling
Proactive outbound strategy
Consultative discovery
Competitive positioning
Closing with clarity
Product fluency
Value articulation
Decisive deal strategy
Pipeline management
KPI management
Diagnosing gaps
Identifying risks
Expanding coverage
Opportunity creation and progression
Forecasting
Deal reviews
Data-backed insights
Sales execution
High-velocity sales cycles
Complex sales cycles
Building a high-performance, high-accountability culture
Trust building
Setting clear expectations
Ownership
Open communication
Hiring
Onboarding
AE development
Exceeding quota
Scaling expertise
Scaling process
Scaling go-to-market effectiveness
Articulating value and differentiation
Interpersonal skills
Leadership skills
Organizational skills
Communication skills

Experience Level

8+ years of sales success
5+ years of leadership experience

Benefits

Remote work
Medical insurance
Flexible time off
Retirement savings plans
Modern family planning

About the Company

Since opening doors in 2009, Square has evolved with the world of commerce, enabling anyone to take payments and never miss a sale. They expanded into software to build integrated, omnichannel solutions for sellers, covering online sales, inventory management, buy now, pay later, appointment booking, customer engagement, and staff management. Financial services tools are embedded at the point of sale, providing merchants access to business loans and cash flow management. Afterpay furthers the goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale. Square is a partner to sellers of all sizes, from large enterprises to small businesses. As sellers grow, so do their solutions, presenting a massive opportunity to build a significant, meaningful, and lasting business that helps sellers worldwide do the same.
Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each brand 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, they are helping build a financial system that is open to everyone.

Equal Opportunity

Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class.
We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances.
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.