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

The Global Seller Onboarding (GSO) team partners directly with Square’s largest and most complex sellers (what we call our clients) to ensure they fully realize the value of Square’s products and services. As a Senior Onboarding Specialist, you will lead the technical onboarding and activation of new merchants, delivering a seamless, scalable, and high-quality onboarding experience.

In this role, you will work cross-functionally with Sales, Account Management, Product, Engineering, and Customer Success to implement Square deployments for primarily SMB and Mid-Market sellers. For certain sellers, you may engage pre-sale to support discovery, solution validation, and the positioning of Square’s professional services offerings. This role is pivotal to Square’s upmarket growth strategy and to shaping the enterprise seller experience from initial solution design through activation.

You Will

• Engage with sellers pre-sale to support discovery, scoping, planning, and solution validation.
• Advise on and document Square's product capabilities and limitations to ensure clear, accurate expectations are set with prospective sellers.
• Own and manage multiple complex onboarding projects concurrently, balancing competing priorities, timelines, and resource constraints.
• Build strong cross-functional partnerships with Sales & Account Management, Customer Success, Product, Marketing, and Engineering teams.
• Collaborate effectively with technical partners and clearly communicate technical requirements to both technical and non-technical stakeholders.
• Proactively identify and manage risk throughout the onboarding lifecycle, ensuring consistent stakeholder communication and successful outcomes.
• Support data entry and data migration activities as part of the onboarding process for select sellers.
• Maintain deep expertise in Square's platform and ecosystem, providing guidance on technical and product capabilities to optimize the seller experience.
• Act as a liaison between sellers and Product teams, translating complex requirements into actionable feature requests and roadmap input.
• Demonstrate professionalism, collaboration, and strong executive presence while working under deadlines with internal and external stakeholders.
• Mentor and support junior team members and contribute to team enablement.
• Identify process gaps and drive improvements by leveraging scalable AI-powered automation.
• Travel up to 10% for client meetings, hardware installations, and other internal events.

You Have

• 4+ years of experience in a customer-facing role, including 3+ years of experience in project management, implementation, or onboarding
• Proven ability to manage multiple complex projects simultaneously across competing priorities, timelines, and resources.
• Strong ability to distill complex requirements into tailored solutions and communicate technical concepts clearly and concisely.
• Working knowledge of project management methodologies, tools, and best practices.
• Experience in the POS, payments, or broader technology industry.