Senior Technical Project Manager

We are seeking a fractional contract (1099) Senior Technical Project Manager with deep experience managing Point-of-Sale (POS) and cashless payment systems to lead complex, cross-functional initiatives from concept through delivery. The ideal candidate brings strong technical acumen, retail systems experience, and the ability to independently translate leadership direction into actionable plans, data insights, and recommendations. The contractor will work with internal and external teams to lead the deployment of a new enterprise system. Expected weekly commitment is 15-20 hours but will depend at what stage of the project and deployment.

Prior experience within a Family Entertainment Center (FEC) environment is strongly preferred, though candidates with broader retail, hospitality, or high-transaction environments will also be considered.

This role requires a self-directed professional who can operate with minimal supervision while maintaining tight alignment with executive and operational leadership.

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Key Responsibilities

• Lead end-to-end delivery of technical projects related to POS platforms, cashless card systems, payment processing, and system integrations
• Serve as the primary liaison between business stakeholders, leadership, vendors, and technical teams
• Translate leadership objectives and operational needs into project plans, system requirements, timelines, and technical recommendations
• Independently analyze data, system performance, and business workflows to provide clear insights and improvement recommendations
• Manage project scope, schedules, budgets, risks, and dependencies across multiple concurrent initiatives
• Coordinate with vendors and internal teams on system implementations, upgrades, migrations, and enhancements
• Ensure solutions meet security, compliance, scalability, and reliability standards
• Identify risks and proactively develop mitigation strategies without reliance on constant oversight
• Provide clear, concise communication to leadership, including status reporting and executive-level summaries
• Support operational teams during rollout, stabilization, and post-implementation review

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Qualifications

• 7+ years of experience in technical project management
• Hands-on experience managing POS systems, payment technologies, or cashless card solutions
• Strong understanding of retail transaction flows, hardware/software integrations, and data reporting
• Proven ability to work independently, taking high-level direction and executing without step-by-step guidance
• Demonstrated success managing cross-functional and vendor-led projects
• Excellent analytical, documentation, and communication skills
• Comfortable operating in fast-paced, operationally critical environments
• Prior experience in a Family Entertainment Center (FEC) environment
• Experience supporting high-volume transaction systems
• Background in retail, hospitality, amusement, or similar customer-facing operations
• Familiarity with system integrations, APIs, and data analysis related to POS platforms
• PMP or similar project management certification (preferred, not required)

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How to Apply

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