Senior Director, Travel Services

Road Scholar • Boston, MA

2d • $119,500 - $144,500 • Remote

About The Position

The Senior Director, Travel Services sets the strategic direction and provides overall leadership for Travel Services, strengthening the function’s capabilities and its ability to deliver a high-quality, consistent participant experience. Leading through a team of senior leaders, this role ensures the operation is effectively led and executed while remaining focused on long-term strategy, innovation, and continuous improvement. The Senior Director designs and leads a function that enables the team to navigate the complexity of the airline landscape, manage high operational demands, and deliver on Road Scholar’s mission and business goals. Road Scholar offers a remote work environment. The compensation range for this exempt level salaried position is $119,500 - $144,500 based on experience.

Requirements

• 8+ years of leading complex service, operations, customer experience, contact center, hospitality, travel, healthcare, or other service-oriented organizations
• 5+ years of experience leading organizational change, process improvement, and operational transformation initiatives
• 5+ years of experience leading leaders, developing emerging leaders and building high-performing teams
• Experience balancing strategic planning with operational execution in a complex, service-oriented environment
• Proven ability to quickly learn complex business functions and lead teams comprised of subject matter experts
• Demonstrated ability to make sound decisions in areas where others possess deeper technical expertise
• Experience building strong partnerships with operational subject matter experts to drive business outcomes
• Strong service orientation and commitment to delivering high-quality customer experiences
• Strategic thinker with the ability to translate vision into action
• Strong change leadership and organizational development skills
• Excellent communication and relationship-building abilities
• Demonstrated ability to lead through ambiguity and complexity
• Ability to balance participant needs, employee experience, and business objectives
• Strong analytical and problem-solving skills
• Ability to lead effectively without being the technical expert in every area of responsibility
• Curiosity and learning agility; quickly develops understanding of complex business processes and operating environments

Responsibilities

• Define and drive the vision and long-term direction for Travel Services, ensuring alignment with organizational priorities
• Establish and communicate a clear service and operating model across inbound, outbound, and support teams
• Ensure the function evolves to meet changing participant and organizational needs
• Lead strategic and systemic improvement efforts across the function
• Champion changes that enhance service quality, efficiency, in both the employee and participant experience
• Translate insight into action by delivering measurable operation and experience improvements
• Serve as the primary cross-department leader for Travel Services, partnering across teams to influence outcomes and drive alignment
• Ensure clarity in roles, responsibilities, and handoffs across functions (e.g., Air Operations, Program teams, PX, PS)
• Connect the work of Travel Services to broader organizational goals and initiatives
• Oversee the establishment of operational goals, KPIs, and best practices that reflect the true goals of the function
• Define performance standards across service, quality, and efficiency, ensuring they are meaningful and actionable
• Ensure a performance management framework is in place, enabling leaders to monitor results and adjust operations in real time to achieve targets
• Lead and develop a team of senior leaders, including the Senior Operations Manager, Senior Training Manager, and the Director, Travel Services
• Design an organizational structure that supports clarity, scalability, and effective spans of control
• Coach leaders to operate at the appropriate level, balancing strategic thinking with execution
• Set direction for the Training function, led by a Senior Manager, to ensure programs effectively build capability and reinforce service, quality, and efficiency standards
• Set direction for the Operations function, led by an Operations Manager, to ensure strong workforce planning, performance monitoring, and actionable insight
• Ensure alignment across Training and Operations to drive consistency in execution and support informed, data-driven decision-making
• Deliver measurable improvements in participant experience, operational efficiency, and team effectiveness
• Position Travel Services as a strategic contributor to the organization’s broader success
• Ensure team efforts are clearly connected to participant impact and business outcomes

Benefits

• Medical, Dental and Vision Insurance (with a substantial employee subsidy!)
• 403(b) Retirement Plan with a company match of 5% after 1 year of employment!
• Up to 20 days of PTO annually, accrued every payroll cycle
• A paid week off, in addition to your PTO, at the end of December to enjoy the holiday season!
• A generous employee discounts on our programs
• As a Road Scholar employee, you can opt-in to receive an IATA membership
• LinkedIn Learning access to all employees amongst other professional development opportunities

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed