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SquareSquare

Onboarding Project Manager

Leads technical onboarding and activation projects for complex enterprise merchants, coordinating pre-sales discovery, integrations, migrations, and issue resolution across technical and commercial teams. Requires substantial customer-facing and project management experience plus familiarity with APIs, system architecture, and payments or technology.

About the job

Responsibilities

  • Lead technical onboarding and activation of new enterprise and strategic merchants.
  • Deliver onboarding and training experiences that drive adoption and long-term seller success.
  • Support pre-sale discovery, project scoping, solution validation, and professional services positioning.
  • Own multiple complex onboarding projects, balancing priorities, timelines, and resources.
  • Build cross-functional partnerships with Sales, Account Management, Customer Success, Solutions Engineering, Partner Engineering, Product, Marketing, and Engineering.
  • Communicate technical requirements clearly to technical and non-technical stakeholders.
  • Evaluate third-party integrations, including POS peripherals, ERP systems, loyalty platforms, and eCommerce systems, for compatibility and feasibility.
  • Identify and manage risks throughout onboarding and maintain stakeholder communication.
  • Support data entry and data migration activities for selected sellers.
  • Maintain expertise in first-party products, the developer platform, and its ecosystem.
  • Translate enterprise requirements into feature requests and product roadmap input.
  • Triage and drive resolution of technical issues during onboarding.

Requirements

  • 6+ years of experience in a customer-facing role and 4+ years in project management, implementation, or onboarding roles.
  • Professional experience with RESTful APIs, webhooks, OAuth, and/or SDK integrations.
  • Ability to understand 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 across competing priorities, timelines, and resources.
  • Ability to distill complex enterprise requirements into tailored solutions and communicate technical concepts clearly.
  • 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 benefits

Skills

REST APIs, Webhooks, OAuth, Sdk Integrations, Api Documentation, System Architecture, Third-Party Integrations, Data Migration, Project Management, Technical Project Tracking, Pos Systems, Payments

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