Director, Information Technology

Established in 2025, The Vacation Group is a full-service travel collective bringing together four distinguished agencies under one unified brand. As an Internova Travel Group brand and members of Travel Leaders Network, The Vacation Group offers a broad portfolio of travel services including cruises, solo cruises, custom luxury vacations, and student and group tours.

Formerly CruCon Cruise Outlet, SinglesCruise, Travel Leaders Vacation Center, and Student Tours, we are comprised of an award-winning team of seasoned travel advisors and customer service professionals. The Vacation Group is committed to delivering exceptional value, expert guidance, and personalized travel experiences across the globe. With strong industry partnerships and a client-first approach, The Vacation Group provides travelers with a seamless planning process and access to unparalleled value and exclusive perks.

The combined legacy of its founding brands has earned recognition from leading travel partners including Royal Caribbean, Celebrity Cruises, Norwegian Cruise Line, Oceania Cruises, and many others — making The Vacation Group a trusted name in the travel industry for service excellence and innovation. For more information about The Vacation Group click here.

Strategic technology executive responsible for leading digital transformation, innovation, and operational excellence across consumer and member-facing platforms. Drives adoption of emerging technologies (AI, cloud, automation) and ensures robust, scalable solutions that deliver business value and superior user experiences. Partners with cross-functional and cross-divisional teams to align technology strategy with organizational goals, foster a culture of agility, and champion data-driven decision-making.

Digital Product Leadership

• Define and evolve product vision for next-generation consumer/member platforms, leveraging AI where possible.
• Lead product roadmap development, integrating feedback from stakeholders, market research, and analytics to prioritize high-impact initiatives.
• Conduct competitive analysis and monitor industry trends (e.g., personalization, cybersecurity, sustainability) to inform strategic direction.
• Oversee full product lifecycle: ideation, development, launch, and continuous improvement, with a focus on rapid iteration and user-centric design.

Program & Project Management

• Champion agile methodologies (Scrum, Kanban) and modern project management tools to accelerate delivery and enhance transparency.
• Proactively identify risks and implement mitigation strategies to ensure timely, on-budget project completion.
• Manage resources across internal teams and external partners, including remote and hybrid workforces.
• Oversee vendor relationships, contract negotiations, and performance management for third-party technology providers.

Technology Operations & Support

• Ensure seamless deployment and support of new applications and enhancements, leveraging DevOps practices for continuous integration and delivery.
• Establish robust incident management, bug tracking, and root cause analysis processes.
• Drive adoption of self-service support, automation, and AI-powered troubleshooting to improve operational efficiency.
• Develop and execute comprehensive launch plans, user onboarding, and change management strategies.

Talent Development & Stakeholder Engagement

• Build and mentor high-performing, diverse technology teams; foster a culture of innovation, collaboration, and continuous learning.
• Facilitate cross-functional alignment and consensus-building across business units.
• Lead training initiatives, including development of digital learning resources and “train the trainer” programs.
• Represent technology function in executive leadership forums, providing strategic insights and updates on digital initiatives.

• 7+ years’ experience in technology leadership, product management, or digital transformation.
• 3+ years managing distributed teams (onsite, remote, hybrid).
• Bachelor’s or Master’s degree in Computer Science, Business, or related field.
• Expertise in Agile, Scrum, and waterfall methodologies; proficiency with modern PM tools (Jira).
• Proven success in delivering complex projects on time and within budget.
• Strong vendor management and negotiation skills.
• Exceptional communication and stakeholder management abilities.
• Experience with travel industry platforms, data analytics, and digital customer experience.
• Ability to lead large-scale change, drive consensus, and present to executive audiences.

PAY AND BENEFITS

Our benefit offerings include choice of two medical plans and two dental plans, vision insurance, flexible spending accounts (FSAs), company-paid life insurance and AD&D, optional additional life insurance and AD&D, disability insurance, paid parental leave, paid time off, 401k Plan with company match, discounted employee travel options, access to LinkedIn Learning webinars and courses. Discounted pet insurance and auto, home, & renters insurance.

The salary range on this job posting/advertising has been developed to give applicants a wide range to comply with pay transparency laws in all states and geographical areas. Many factors, such as years of experience, geographical location, budget etc. are considered when determining the starting rate of pay. The salary range posted represents the pay range for U.S. candidates. If the job posting indicates that the role is available for international candidate consideration, the salary range will be based on the local market for the country where the candidate would be working.

This role may be eligible for an incentive, commission, bonus, or a discretionary bonus program based on the company’s financial goal achievement and individual performance.

Internova Travel Group is an Equal Opportunity Employer. We make employment decisions without regard to age, race, religion, national origin, gender, disability, veteran status, genetic information, sexual orientation and gender identity or any other protected class.

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