Manager of Project Management

World Travel Holdings is seeking an experienced, remote Manager of Project Management to help us deliver innovative solutions that make leisure travel more accessible and fun. This role is responsible for direct management of project delivery staff, including contract resources, and acts as a Program Manager to ensure alignment, efficiency, and success across the portfolio. The Manager will drive end-to-end delivery, foster a culture of accountability and continuous improvement, and build strong cross-functional partnerships across IT and business teams.

About World Travel Holdings
World Travel Holdings is the nation’s largest cruise agency and award-winning leisure travel company with a portfolio of nearly 40 diverse brands. In addition to owning some of the largest brands distributing cruises, villas, resort vacations, car rentals, resort day passes and luxury travel services, World Travel Holdings has a vast portfolio of private-label partnerships comprised of top leisure travel providers, including almost every U.S. airline, leading hotel brands and prominent corporations. The company also operates a top-rated travel agency franchise and is consistently recognized as an industry leader in employee engagement and work-at-home employment. Its global presence includes operating multiple cruise brands in the United Kingdom. World Travel Holdings has offices in Wakefield, Mass.; Ft. Lauderdale, Fla.; and Chorley, England. For more information, visit WorldTravelHoldings.com.

Program Management & Delivery Oversight

• Lead the development and execution of long-range portfolio plans, defining scope, milestones, timelines, and budgets
• Establish governance structures for decision-making, escalation, and reporting
• Oversee resource planning and allocation for project managers, scrum masters, business analysts, and cross-functional delivery teams
• Act as Program Manager across all delivery tracks, managing dependencies, risks, and milestones holistically
• Provide unified program status, risks, and priorities to leadership
• Ensure scope, timeline, and budget adherence for all projects
• Proactively escalate issues and provide solution-oriented recommendations
• Manage projects through the full life cycle: Initiating, Planning, Executing, Monitoring & Controlling, and Closing
• Lead Scrum Masters in effective Agile ceremonies and Project Managers in roadmap delivery

Leadership & People Management

• Manage, coach, and develop Project Managers and Scrum Masters to operate effectively in a hybrid delivery model
• Set clear performance expectations and ensure accountability for delivery commitments
• Foster a culture of ownership, collaboration, and psychological safety
• Provide regular feedback and career growth guidance
• Train, mentor, and support teams in Agile and Waterfall methodologies

Process & Standards

• Build, communicate, and implement a clear and consistent hybrid delivery methodology across all teams
• Maintain and improve governance practices and tools (project intake, prioritization, status reporting, retrospectives, planning)
• Ensure the effective configuration, administration, and utilization of project management platforms such as Jira, SmartSheets and SharePoint
• Ensure consistent documentation practices (RAID tracking, status reports, change logs)
• Continuously review and update standards based on lessons learned and industry best practices
• Develop and maintain a high-level understanding of delivered work to challenge plans, validate assumptions, and proactively identify gaps, risks, and dependencies

Stakeholder Engagement

• Ensure stakeholder alignment on program goals, success metrics, and dependencies
• Build strong, trust-based relationships with Product, Engineering, and business leaders
• Represent the delivery team in leadership forums, ensuring alignment with business priorities
• Translate business objectives into actionable delivery plans.
• Provide executive-level reporting that translates Agile progress into milestone-based tracking
• Facilitate executive workshops, Steering Committees and cross-functional discovery sessions

Risk & Issue Management

• Build structures to capture and validate assumptions for all program/project plans
• Identify, track, and resolve risks and issues at both project and program levels
• Ensure delivery teams have the support, decisions, and clarity needed to succeed
• Anticipate bottlenecks and act early to remove blockers

• Bachelor’s degree in Information Technology, Business, or related field required
• 8+ Years of relevant project leadership experience in a hybrid waterfall/agile environment
• 3+ years as a Scrum Master
• PMP and Certified Scrum Master Certification or equivalent  
• Working knowledge of agile methodology such as Scrum or Kanban to deliver end to end solutions
• Expert in project management tools like Jira, Smartsheets, SharePoint, etc.
• Experience managing vendors
• Experience working in a remote environment, managing teams and projects leveraging virtual collaboration tools
• Excellent communication and interpersonal skills
• Strong analytical and problem-solving skills