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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.
Job Responsibility:
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
Manage pipeline and KPIs with rigor
Run disciplined weekly pipeline, forecast, and deal reviews
Use data-backed insights to coach AE effectiveness
Build a high-performance, high-accountability culture
Hire, onboard, and develop AEs
Scale expertise, process, and go-to-market effectiveness
Partner and innovate across the business
Engage deeply with community networks, partners, and local events
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
Excellent interpersonal, leadership, organizational, and communication skills