# Onboarding Project Manager

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Remote
**Role:** Technical Program Management
**Experience:** 6+ years
**Skills:** REST APIs, Webhooks, OAuth, Sdk Integrations, Api Documentation, System Architecture, Third-Party Integrations, Data Migration, Project Management, Technical Project Tracking, Pos Systems, Payments
**Posted:** 2026-08-07

> 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.

## Job Description

## 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

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