Project Manager, Data Analyst, IT Business Analyst

At Dream Giveaway, your work does more than drive results—it helps change lives. We run high-impact digital campaigns that combine premium automotive and lifestyle prizes with charitable fundraising. We support veterans' and children's charities and deliver engaging, purpose-driven experiences to a national audience. We're a fast-moving, mission-driven organization where creativity, accountability, and collaboration come together to make a real-world impact.

Dream Giveaway has been acquired and is now part of the Jumbo Interactive Group —an alignment that strengthens our mission, expands opportunity, and supports long-term growth for our people. This partnership provides greater stability, expanded career growth opportunities across a broader organization, and access to shared resources and expertise.

In this role, you ll lead Dream Giveaway s transformation to the JLP platform—orchestrating a complex, structured transition that balances speed with stability. You ll be the central hub connecting Dream Giveaway teams, Jumbo Group counterparts, IT, vendors, and external partners. Your work will span discovery and design through to launch and stabilization, ensuring the new platform supports Dream Giveaway s mission-driven operations, enables growth, and maintains compliance throughout.

• Lead the end-to-end implementation of Dream Giveaway s new core platform (JLP), ensuring a structured, low‑risk transition that supports long-term operational scalability.

• Deeply learn and document Dream Giveaway s current operations, systems, and regulatory/compliance requirements, then translate them into clear, future‑state processes.

• Own project planning and governance: develop and maintain project plans and milestones. Create and manage RAID (Risks, Assumptions, Issues, Dependencies) logs and a clear RACI (Responsible, Accountable, Consulted, Informed). Keep all stakeholders aligned across Dream Giveaway and the Jumbo Group.

• Drive detailed business process mapping, requirements gathering, and solution design, working closely with counterparts in Jumbo to align business needs with platform capabilities.

• Coordinate data migration and integration activities, ensuring data quality, accuracy, reconciliation, and minimal disruption to day‑to‑day operations.

• Act as the central point of contact between Dream Giveaway, Jumbo Group teams, IT, external vendors, and developers—facilitating decisions, clarifying requirements, and managing expectations.

• Proactively identify, assess, and surface project risks and dependencies early, and lead mitigation and escalation where needed.

• Track and report on progress, budget, and outcomes for leadership; provide clear, data‑driven updates and insights to support decision‑making.

• Champion change management across a small, entrepreneurial team—communicating clearly, supporting adoption of new processes and tools, and helping teams adjust to new ways of working.

• Lead the day‑to‑day planning and delivery of the JLP platform implementation for Dream Giveaway, working closely with stakeholders at Dream Giveaway and across Jumbo Group.

• Deeply understand current Dream Giveaway operations, compliance requirements, and fundraising workflows, translating them into clear, documented future‑state processes.

• Run business process mapping sessions with teams such as finance, sales, marketing, IT, and operations to capture requirements, dependencies, and risks.

• Build and maintain the project plan, governance model, RACI, and milestone roadmap; track progress against timelines and budget, and adjust as needed.

• Coordinate activities across multiple cross‑functional and external teams, including local leadership, IT, and external developers, to ensure aligned, on‑time delivery.

• Own day‑to‑day vendor and stakeholder communications: schedule and facilitate meetings, circulate agendas and notes, and drive follow‑ups to resolution.

• Oversee data migration and integration activities, working with technical teams to ensure data accuracy, reconciliation, and minimal disruption to live operations.

• Proactively surface risks, issues, and trade‑offs early; prepare options…