Product Specialist Manager, Square

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. About the Role Square is looking for a Product Specialist Manager to lead a team of specialists focused on helping sellers understand, adopt, and get more value from Square's growing product ecosystem. Our Product Specialists combine deep product expertise with strong customer and commercial skills. They partner closely with Account Executives and Account Managers on opportunities where specialized product knowledge can help address complex seller needs, accelerate adoption, and improve outcomes. As a Product Specialist Manager, you'll lead and develop a team of specialists, deploy their expertise against our highest-priority seller and product opportunities, and help strengthen product knowledge across the broader sales organization. You'll also serve as an important connection between our frontline teams and Product—surfacing seller insights, identifying friction, and helping improve how we bring Square's products to market. This is a hands-on leadership role for someone equally comfortable coaching a team, engaging in complex seller opportunities, building deep product expertise, and partnering cross-functionally to improve seller outcomes. What You'll Do Lead a High-Performing Product Specialist Team • Lead, coach, and develop a team of Product Specialists supporting Account Executives, Account Managers, and their sellers. • Build deep product expertise alongside strong consultative and customer engagement skills. • Establish clear priorities and operating rhythms to ensure specialist resources are deployed against the highest-impact opportunities. • Foster a culture of ownership, customer focus, collaboration, and continuous improvement. • Manage team performance, development, capacity, and engagement. Support Strategic Seller Opportunities & Product Adoption • Partner with Account Executives and Account Managers on high-value and complex opportunities where specialized product expertise can improve seller outcomes. • Coach specialists through discovery, product positioning, solution design, objection handling, and complex product conversations. • Engage directly with sellers when additional product expertise or leadership can help advance an opportunity. • Help sellers understand how Square's products can address their business needs and unlock greater value from the Square ecosystem. • Support GTM and Product priorities by deploying specialist expertise toward strategic and underpenetrated products. Scale Product Expertise Across Sales • Increase product knowledge and confidence across Account Executives, Account Managers, and other frontline teams. • Partner with Enablement, Product, and Marketing to develop product guidance, playbooks, messaging, training, and other resources. • Identify recurring knowledge gaps and seller objections and translate them into scalable enablement opportunities. • Develop repeatable approaches that allow frontline teams to independently navigate more product conversations over time. Connect Seller Insights to Product & GTM • Serve as a strong feedback loop between sellers, frontline sales teams, and Product. • Surface recurring seller needs, product gaps, objections, and adoption barriers. • Partner across Product, Sales, Marketing, GTM Strategy & Operations, Data Science, and Enablement to improve product commercialization and seller experience. • Use seller, product, and performance insights to continuously improve how specialist resources are prioritized and deployed. Success Metrics • Product adoption and attach rate • Seller opportunities supported and influenced • Conversion and outcomes of specialist-supported opportunities • Specialist engagement and utilization • Team performance and development • Increased product knowledge and self-sufficiency across frontline teams • Effectiveness of product enablement and specialist support • Quality and impact of seller insights surfaced to Product and GTM teams What You'll Bring • 7+ years of experience in B2B sales, account management, product specialization, solution consulting, fintech, SaaS, payments, or another complex customer-facing environment, including experience leading and developing teams. • Experience supporting complex products or solutions that require consultative discovery and deep product expertise. • Strong people leadership skills with a track record of coaching and developing high-performing teams. • Demonstrated ability to partner effectively with Account Executives and Account Managers in a specialist, overlay, or consultative model. • Strong customer and commercial instincts with the ability to connect seller needs to product capabilities and business value. • Ability to translat