Mid-Market Account Manager, Retail

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 Square’s Strategic Account Management organization is seeking an experienced professional to drive growth and retention within our Retail Strategic Account Management program. This team partners with some of Square’s largest retail sellers – businesses redefining how technology shapes the customer and merchant experience. In this role, you’ll serve as a trusted advisor to retail executives and operators, helping them simplify operations, improve performance, and scale using Square’s ecosystem. You’ll uncover opportunities for growth, develop tailored retention strategies, and collaborate closely with Product, Engineering, Finance, and Marketing to deliver seamless, impactful outcomes for our most valuable sellers. The ideal candidate is strategic, empathetic, and passionate about building long-term relationships. You excel at navigating complex organizations, aligning internal teams, and finding creative ways to solve customer challenges. You thrive in dynamic environments, advocate for your clients, and play a key role in shaping how Square continues to serve the upmarket retail space. You Will Own and maintain relationships across a portfolio of ~160 strategic retail sellers, driving account expansion, retention, and satisfaction Consult with business owners and operators to uncover opportunities across operations, payments, and commerce Design and implement customized solutions that drive measurable business results Act as the voice of the customer, advocating for upmarket seller needs with Product, Engineering, and Operations teams Collaborate cross-functionally with Account Executives, Product Managers, and Solution Engineers to deliver integrated, scalable outcomes Where and when appropriate, visit customers in-person for negotiations and/or churn prevention Negotiate and manage contracts and pricing, ensuring mutual wins and long-term success Deliver white-glove support, resolving critical issues and proactively driving engagement You Have 5+ years of experience in sales or account management, ideally within SaaS, payments, or POS technology Proven success growing and retaining a book of business Consistent overperformance on key metrics and revenue targets Strong discovery and consultative selling skills Retail industry experience preferred, but not required Technical solutioning skills, including requirements gathering and translating customer needs into scalable solutions Demonstrated success retaining and expanding strategic accounts Experience negotiating contracts and pricing with senior stakeholders Exceptional written and verbal communication skills – storytelling is central to this role Creative, strategic problem-solver who thrives in ambiguous envi