Head of Field Sales

After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions - to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Today, we are a partner to sellers of all sizes - large, enterprise‑scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

Manager, Field Sales, Manchester

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 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.

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.

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

Hold the team to a high bar of execution while providing the clarity, structure, and hands‑on coaching needed to meet it.

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

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

Experience scaling and overseeing large Field Sales teams

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.

We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances.