[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.ResponsibilitiesDeliver a remarkable onboarding and training experience that drives adoption and long-term seller successPartner with Account Executives and Account Managers during pre-sale and onboarding to scope projects, validate proposed solutions, and support professional services positioningServe as a bridge between enterprise sellers and Product teams, ensuring seller needs meaningfully inform Square’s product roadmapFunction as the technical liaison between sellers, their technical teams and functions, and internal technical stakeholders like Solutions Engineering, Partner Engineering, Product, Engineering, etcEngage with sellers pre-sale to support discovery, scoping, planning, and solution validationAdvise 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 sellersOwn and manage multiple complex onboarding projects concurrently, balancing competing priorities, timelines, and resource constraintsBuild strong cross-functional partnerships with Sales & Account Management, Customer Success, Solutions Engineering, Partner Engineering, Product, Marketing, and Engineering teamsCollaborate effectively with technical partners and clearly communicate technical requirements to both technical and non-technical stakeholdersEvaluate third-party partner integrations (POS peripherals, ERP systems, loyalty platforms, eCommerce, etc.) for compatibility and feasibility with Square's platformProactively identify and manage risk throughout the onboarding lifecycle, ensuring consistent stakeholder communication and successful outcomesSupport data entry and data migration activities as part of the onboarding process for select sellersMaintain deep expertise in Square’s first-party products and developer platform and ecosystem, providing guidance on technical and product capabilities to optimize the seller experienceAct as a liaison between enterprise sellers and Product teams, translating complex requirements into actionable feature requests and roadmap inputTriage and drive resolution of technical issues during onboarding, partnering with internal stakeholders to unblock sellersDemonstrate professionalism, collaboration, and strong executive presence while working under deadlines with internal and external stakeholdersSkills6+ years of experience in a customer-facing role and 4+ years of experience in project management, implementation, or onboarding rolesExperience working with RESTful APIs, webhooks, OAuth, and/or SDK integrations in a professional capacityAbility to understand and reason about system architectures, third-party integrations, and multi-system data flowsAbility to understand developer documentation, API references, and technical project tracking toolsProven ability to manage multiple complex projects simultaneously across competing priorities, timelines, and resourcesStrong ability to distill complex enterprise requirements into tailored solutions and communicate technical concepts clearly and conciselyWorking knowledge of project management methodologies, tools, and best practicesExperience in the POS, payments, or broader technology industryBenefitsRemote workMedical insuranceFlexible time offRetirement savings plansModern family planningCompany OverviewSince we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. It was founded in 2009, and is headquartered in San Francisco, California, USA, with a workforce of 1001-5000 employees. Its website is https://block.xyz.Company H1B SponsorshipSquare has a track record of offering H1B sponsorships, with 22 in 2026, 257 in 2025, 253 in 2024, 260 in 2023, 297 in 2022. Please note that this does not guarantee sponsorship for this specific role.