[Remote] Enterprise Seller Onboarding (ESO) Technical Project Manager

Note: The job is a remote job and is open to candidates in USA. Square is a company that has evolved to provide integrated, omnichannel solutions for sellers. The Enterprise Seller Onboarding (ESO) Technical Project Manager will lead the onboarding and activation of new enterprise and strategic merchants, ensuring a seamless experience while collaborating cross-functionally to design and implement complex deployments.

Responsibilities

• 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 functions, and internal technical stakeholders like Solutions Engineering, Partner Engineering, Product, Engineering, etc
• 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

Skills

• 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

Benefits

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

Company Overview

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