Role
Square is building a world‐class, high‐accountability field sales organization — and we're looking for a leader 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 — 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.
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
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.
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