Project Manager

Jumbo Interactive • Largo, FL

9d • $110,000 - $145,000 • Hybrid

About The Position

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.
What you will be doing
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.
What Your Day to Day looks like
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 and recommendations, and escalate decisions to Ryan and other leaders when required.
Prepare and deliver clear status updates, reports, and analysis for leadership, including Ryan and the Dream Giveaway leadership team, highlighting progress, risks, and impacts.
Support change management by communicating upcoming changes, coordinating training and handover, and helping teams adapt to new processes and tools.
How we will measure success in this role
In your first 3–6 months, you will have led the JLP platform implementation through discovery, design, and build, with a clear, agreed roadmap to go‑live across core Dream Giveaway workflows.
Within 6–12 months, the JLP platform will be live and stable for day‑to‑day use, with key fundraising, marketing, finance, and operations processes documented, communicated, and adopted by relevant teams.
The transition will be delivered on time and within the agreed budget, with minimal disruption to live campaigns, donor experience, and internal operations.
Leadership will have clear, data‑driven visibility into project status, risks, and business impact through regular reporting and updates that you own.
What We Would Like You To Bring
These are the core requirements for the role:
5+ years' experience as a Project Manager / Business Analyst leading complex SaaS (software-as-a-service) or platform implementations, ideally end‑to-end (discovery through go‑live and stabilization)
Proven track record delivering projects on time and on budget, with strong governance, risk management, and stakeholder communication
Strong business analysis skill set, including requirements gathering, process mapping, future‑state design, and documentation (RACI, governance models, roadmaps, etc.)
Hands‑on experience with data migration and systems integration, including reconciliation and ensuring data accuracy
Comfortable working closely with executives and senior stakeholders, translating business needs into clear, structured delivery plans
Experience coordinating across multiple cross‑functional teams and external vendors in a fast-moving environment
Familiarity with waterfall or hybrid delivery methodologies and the judgment to balance structure with pragmatism
Salary: $110,000–$145,000 USD base salary, depending on experience and skills.
Employment Type: Fixed-term contract, 9–12 months duration.
Our Ways of Working
At Dream Giveaway, we move fast—but with purpose. We've built a collaborative, respectful, and driven culture that values ownership, transparency, and doing the right thing for our donors, charity partners, and each other. This is a hybrid role based in our Largo office; expect to work on-site, e.g., initially FT in the office, then moving to 3 days per week and remotely from home for the remaining days.
Find Your Freedom at Dream Giveaway
As a team member at Dream Giveaway, look forward to:
Competitive, market-aligned compensation
Flexible, role-appropriate work arrangements
Hands-on learning across marketing, operations, and partnerships with direct access to leadership and decision-makers
Strong focus on career and skills development with opportunities to grow in a scaling organization
We are a 2026 Circle Back Initiative Employer – we commit to respond to every applicant.

Requirements

• 5+ years' experience as a Project Manager / Business Analyst leading complex SaaS (software-as-a-service) or platform implementations, ideally end‑to-end (discovery through go‑live and stabilization)
• Proven track record delivering projects on time and on budget, with strong governance, risk management, and stakeholder communication
• Strong business analysis skill set, including requirements gathering, process mapping, future‑state design, and documentation (RACI, governance models, roadmaps, etc.)
• Hands‑on experience with data migration and systems integration, including reconciliation and ensuring data accuracy
• Comfortable working closely with executives and senior stakeholders, translating business needs into clear, structured delivery plans
• Experience coordinating across multiple cross‑functional teams and external vendors in a fast-moving environment
• Familiarity with waterfall or hybrid delivery methodologies and the judgment to balance structure with pragmatism

Responsibilities

• 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 and recommendations, and escalate decisions to Ryan and other leaders when required.
• Prepare and deliver clear status updates, reports, and analysis for leadership, including Ryan and the Dream Giveaway leadership team, highlighting progress, risks, and impacts.
• Support change management by communicating upcoming changes, coordinating training and handover, and helping teams adapt to new processes and tools.

Benefits

• Competitive, market-aligned compensation
• Flexible, role-appropriate work arrangements
• Hands-on learning across marketing, operations, and partnerships with direct access to leadership and decision-makers
• Strong focus on career and skills development with opportunities to grow in a scaling organization

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed