Mid-Market Sales Manager

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. 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. Afterpay furthers our 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.

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. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

We're building a team of standout sales leaders, the kind who raise the performance of everyone around them.

As a Sales Manager, you'll lead a team of Account Executives and own one of our most critical growth levers: developing talent that consistently outperforms. This role is about building a high-performance sales organisation where every hire raises the bar, every coaching conversation sharpens execution, and every decision is grounded in data. You'll bring the rigour, along with energy! 

You'll be expected to coach in the work, not after it. You'll diagnose pipeline health before it becomes a forecasting problem, develop future leaders before promotions become necessary, and create an operating rhythm that enables predictable, repeatable growth.

You'll partner cross-functionally to improve how we sell, challenge the status quo, and continuously raise the talent bar across the organisation. Success is measured not only by quota attainment, but by the strength of your team, the quality of your pipeline, and the leaders you develop.

Build a High-Performance Team

• Hire Account Executives who can run complex, multi-stakeholder deals, and raise the bar with every addition to your team.
• Develop a culture of ownership, accountability, continuous learning and high standards.
• Identify future top performers early and create development plans that accelerate their growth.

Co-Sell on Complex Deals

• Sell alongside your team in discovery, business case development and negotiation on your most important pursuits.
• Engage senior stakeholders directly, including owners, operations and finance, and help your team multi-thread rather than sell to a single champion.
• Bring commercial judgment to pricing, deal structure and competitive displacement.
• Advance the deal while leaving the AE more capable of running the next one without you.

Coach Through Data & Business Intelligence

• Lead your business through rigorous pipeline inspection, forecasting and performance diagnostics.
• Use leading indicators to identify performance gaps early and coach reps toward sustainable improvement.
• Turn data into action by identifying trends, diagnosing root causes and driving measurable improvements across your team.
• Forecast accurately on long-cycle deals, which depends on stage integrity rather than optimism.

Drive Operational Excellence

• Establish predictable operating rhythms around forecasting, pipeline management and business reviews.
• Build disciplined execution that creates consistent, repeatable revenue outcomes.
• Continuously improve how your team sells by refining processes, simplifying execution and eliminating friction.
• Build repeatable plays for how this segment is won, from implementation and expansion.

Lead Through Influence

• Partner closely with Sales Leadership, Marketing, Enablement, Operations, Partnerships and Product to improve the customer journey and strengthen commercial execution.
• Use customer insights and field intelligence to shape strategy and influence product evolution.
• Lead through change by helping your team adapt quickly while maintaining high performance.

You Have

• 6+ years experience as a sales manager, including time leading teams selling into complex, multi-stakeholder accounts with cycles measured in months
• Experience hiring, ramping and retaining Account Executives who can run considered, competitive deals
• Experience developing already strong performers into people who win larger and more complex deals
• Proven track record in collaborating across different teams with the ability to inspire change
• Leadership and coaching experience and a desire to help others be their best
• Expertise in creating structure around sales metrics and managing yourself and others to achieve these metrics, including forecast accuracy on long-cycle deals
• An understanding of how to refine decision-making and consider the downstream and upstream effects of potential decisions

[[INSERT EEOC STATEMENT HERE]]