Enterprise Seller Onboarding Technical Project Manager

Role Description

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.

• Engage pre-sale to support discovery, solution validation, and the positioning of Square’s professional services offerings.
• Work cross-functionally with Sales, Account Management, Product, Engineering, and Customer Success to design and implement complex Square deployments.
• Discuss API/SDK product capabilities and evaluate third-party partner integrations.
• Deliver a remarkable onboarding and training experience that drives adoption and long-term seller success.
• Partner with Account Executives and Account Managers during pre-sale and onboarding to scope projects, validate proposed solutions, and support professional services positioning.
• Serve as a bridge between enterprise sellers and Product teams, ensuring seller needs meaningfully inform Square’s product roadmap.
• Function as the technical liaison between sellers, their technical teams, and internal technical stakeholders.

Qualifications

• 6+ years of experience in a customer-facing role.
• 4+ years of experience in project management, implementation, or onboarding roles.
• Experience working with RESTful APIs, webhooks, OAuth, and/or SDK integrations.
• Ability to understand and reason about system architectures, third-party integrations, and multi-system data flows.
• Proven ability to manage multiple complex projects simultaneously across competing priorities, timelines, and resources.
• Strong ability to distill complex enterprise requirements into tailored solutions.
• Working knowledge of project management methodologies, tools, and best practices.
• Experience in the POS, payments, or broader technology industry.

Requirements

• Engage with sellers pre-sale to support discovery, scoping, planning, and solution validation.
• Advise on and document Square’s first-party product capabilities and limitations.
• Own and manage multiple complex onboarding projects concurrently.
• Build strong cross-functional partnerships with various teams.
• Collaborate effectively with technical partners and communicate technical requirements.
• Evaluate third-party partner integrations for compatibility and feasibility.
• Proactively identify and manage risk throughout the onboarding lifecycle.
• Support data entry and data migration activities as part of the onboarding process.
• Maintain deep expertise in Square’s first-party products and developer platform.
• Act as a liaison between enterprise sellers and Product teams.
• Triage and drive resolution of technical issues during onboarding.
• Demonstrate professionalism, collaboration, and strong executive presence.

Benefits

• Remote work options.
• Medical insurance.
• Flexible time off.
• Retirement savings plans.
• Modern family planning options.