[Remote] Program Management Specialist

Note: The job is a remote job and is open to candidates in USA. High Trail is working with a financial services and fintech client on the post-acquisition integration of a Gibraltar-based/EU payments entity. The Program Management Specialist will assess regulated systems, develop regulatory documentation, define integration sequencing, and create a phased technology migration roadmap while advising senior stakeholders through a complex, multi-year integration.

Responsibilities

• Assess the current state of controlled and regulated systems inherited through the acquisition and identify what requires regulatory approval before migration or change
• Prepare and help shape the regulatory approval packet/documentation required for system and organizational changes
• Define integration sequencing based on regulatory dependencies, technical dependencies, and risk
• Develop a phased migration plan that accounts for end-user experience, particularly where users may need to operate across multiple systems during transition
• Evaluate and plan the integration approach for identity/productivity/collaboration tools, including Microsoft 365, Google Workspace, and Okta
• Advise senior stakeholders on prioritization and sequencing under ambiguity, bringing structure to a complex, multi-year integration effort
• Operate with a risk-mitigation mindset, given incomplete confidence in prior assessment work completed by a previous consulting engagement

Skills

• • Demonstrated experience assessing regulated or controlled systems within a European regulatory context
• • Proven ability to identify regulatory dependencies, technical dependencies, and recommend sequencing across a large, complex system landscape
• • Strong program/project management experience leading complex technology integrations, ideally within M&A environments
• • Direct experience preparing or contributing to regulatory packets/documentation required for system or organizational change
• • Seniority and judgment to operate independently under ambiguity, advising on what should be prioritized from both a regulatory and technical standpoint
• • Direct experience with GDPR or comparable European regulatory frameworks
• • Experience with Gibraltar/EU-specific regulatory processes
• • Prior experience with cross-border integrations, particularly EU-to-US
• • Experience migrating Microsoft 365 to Google Workspace
• • Broader collaboration and productivity tool migration experience, even without this exact M365-to-Google transition

Benefits

• Remote work

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