Onboarding Project 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

The Enterprise Seller Onboarding team partners directly with Square’s largest and most complex sellers to ensure they fully realize the value of Square’s products and services. As an Enterprise Seller Onboarding (ESO) Technical Project Manager, you will lead the technical onboarding and activation of new enterprise and strategic merchants, delivering a seamless, scalable, and high-quality onboarding experience.

In this role, you will engage pre-sale to support discovery, solution validation, and the positioning of Square’s professional services offerings. You will work cross-functionally with Sales, Account Management, Product, Engineering, and Customer Success to design and implement complex Square deployments. You’ll have a strong ability to discuss API/SDK product capabilities and the technical background to evaluate and discuss third party partner integrations. This role is pivotal to Square’s upmarket growth strategy and to shaping the enterprise seller experience from initial solution design through activation.

A successful ESO Project Manager will:

1. Deliver a remarkable onboarding and training experience that drives adoption and long-term seller success.
2. Partner with Account Executives and Account Managers during pre-sale and onboarding to scope projects, validate proposed solutions, and support professional services positioning.
3. Serve as a bridge between enterprise sellers and Product teams, ensuring seller needs meaningfully inform Square’s product roadmap.
4. Function as the technical liaison between sellers, their technical teams and functions, and internal technical stakeholders like Solutions Engineering, Partner Engineering, Product, Engineering, etc.

You Will

• Engage with sellers pre-sale to support discovery, scoping, planning, and solution validation.
• Advise on and document Square’s first-party product capabilities (including the Square developer platform and its public APIs) 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, Solutions Engineering, Partner Engineering, Product, Marketing, and Engineering teams.
• Collaborate effectively with technical partners and clearly communicate technical requirements to both technical and non-technical stakeholders.
• Evaluate third-party partner integrations (POS peripherals, ERP systems, loyalty platforms, eCommerce, etc.) for compatibility and feasibility with Square's platform.
• 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 first-party products and developer platform and ecosystem, providing guidance on technical and product capabilities to optimize the seller experience.
• Act as a liaison between enterprise sellers and Product teams, translating complex requirements into actionable feature requests and roadmap input.
• Triage and drive resolution of technical issues during onboarding, partnering with internal stakeholders to unblock sellers.
• Demonstrate professionalism, collaboration, and strong executive presence while working under deadlines with internal and external stakeholders.

You Have

• 6+ years of experience in a customer-facing role and 4+ years of experience in project management, implementation, or onboarding roles.
• Experience working with RESTful APIs, webhooks, OAuth, and/or SDK integrations in a professional capacity.
• Ability to understand and reason about system architectures, third-party integrations, and multi-system data flows.
• Ability to understand developer documentation, API references, and technical project tracking tools.
• Proven ability to manage multiple complex projects simultaneously across competing priorities, timelines, and resources.
• Strong ability to distill complex enterprise 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.