Bespoke Travel Designer & Operations Lead

About the Role

We are seeking an experienced Bespoke Travel Designer & Operations Lead to join a VIP Guest Services team that creates once-in-a-lifetime journeys for a select group of high-profile guests. You will own the end-to-end creation of a small number of fully custom, never-been-done-before trips, from initial concept through on-the-ground operations, sourcing exclusive homes and experiences and choreographing them into flawless itineraries. Over time, the role is expected to grow to lead a small team of Travel Specialists supporting a portfolio of loyal guests year-round. This is a hands-on role for a creative, well-connected travel product builder who thrives on moving quickly.

Key Responsibilities

• Brainstorm, research, scout, and build a portfolio of custom small-group and private trips tailored to distinct guest profiles, from luxury travelers to families to adventure seekers
• Design complete itineraries that cannot be booked anywhere else, unlocking unique destinations, cultural moments, homes, and experiences
• Own the operational plan for each trip, including transportation, timing, luggage and group movement, insurance, and contingency planning for last-minute changes
• Source and secure accommodations on or off platform, negotiate favorable rates and amenities with vendors, and manage guest budgets
• Interface with guests, travel coordinators, luxury home owners, realtors, and travel suppliers from initial contact through booking, payment, and pre-, on-, and post-trip follow-up
• Serve as a point of contact for guests during travel, resolving issues and emergencies as they arise
• Build and maintain relationships with luxury home owners, villa and real estate partners, and experience vendors to ensure high-quality delivery and preferential treatment
• Provide personalized, discreet service while maintaining strict confidentiality
• Collaborate with internal stakeholders, including program and communications partners, to align trips with guest expectations and broader program goals
• Meet or exceed key sales and service performance indicators
• As the team grows, lead, coach, and develop Travel Specialists, setting the standard for high-touch guest engagement

Qualifications

Required

• Proven experience designing and operating bespoke small-group or private trips for discerning clientele, with real examples of trips you built from concept to completion
• Background with a tour operator, luxury travel design firm, premium membership travel program, or comparable travel product-development environment
• Strong operational planning skills, including group logistics, vendor coordination, and contingency management
• Global travel destination knowledge and an established network of suppliers, property owners, and experience providers
• Excellent communication and interpersonal skills with the ability to build trust with high-profile clients and internal stakeholders
• Professional demeanor, discretion, and sound business judgment
• Highly organized, resourceful, and able to prioritize and deliver on commitments in a fast-paced, entrepreneurial environment
• Ability to travel as needed and to work a flexible schedule, including some weekends

Preferred

• BA/BS in Business Administration, Hospitality, Tourism, or a related field
• 10+ years of luxury travel experience
• 5+ years of team management experience
• Experience with luxury villa or private home rentals
• Availability aligned with North American or European time zones

Key Details

• Start date: October 13, 2026
• Duration: Through December 31, 2027, with potential for extension or conversion to a permanent role
• Location: Remote (within the U.S.)
• Work schedule: Full-time, 40 hours per week; flexible schedule including some weekends and travel
• Pay rate: $65-$75 per hour + benefits (medical, dental, vision, 401K)
• Work Authorization: Must be authorized to work in the U.S. without sponsorship.
• Engagement: W2 Contract role through Maleda Tech.