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Head of Bookings

Location: Office Based Amsterdam, The Netherlands

Department: Bookings & Customer Service

Reports to: Chief Executive Officer (CEO)

Type: Full-time

About One of a Kind Travel

One of a Kind Travel is on a mission to become the leading luxury villa and vacation rental platform in Europe. We pride ourselves on delivering exceptional, personalized service to high-end clients, ensuring that every booking is seamless from start to finish. With rapid growth across multiple markets, we are building a world-class team that shares our passion for excellence and customer experience.

Job Overview

We are looking for a Head of Bookings to lead and expand our Bookings Department. This role requires a dynamic, hands-on leader who will manage and grow our team of booking agents. The ideal candidate will not only manage daily operations but also convert booking requests, set up processes and tools and ensure both commercial and operational excellence. We need someone who can wear multiple hats – managing a team, handling bookings themselves and ensuring that One of a Kind Travel provides the best customer experience in the industry.

Key Responsibilities

Team Leadership & Management

• Manage and mentor a growing team of booking agents, ensuring high performance, motivation and a customer-first mindset.

• Recruit, train and develop the bookings team, ensuring the department is fully resourced to meet growing business demands.

• Define and monitor individual and team KPIs, providing regular feedback and coaching to improve performance.

• Conduct regular one-on-ones, team meetings and performance reviews to ensure continuous development.

Operational Excellence

• Establish and improve booking processes, workflows and best practices to ensure high efficiency and customer satisfaction.

• Implement tools and technologies that streamline operations and provide actionable insights for performance improvement.

• Ensure timely responses to booking requests, general inquiries and follow-ups, providing an outstanding customer experience.

• Monitor team workload and task distribution to ensure requests are handled efficiently and without overlap.

Commercial Focus

• Actively handle booking requests and inquiries, ensuring a high conversion rate from requests to bookings.

• Work closely with the account management (supply) and marketing teams (demand) to align on targets, ensuring a seamless handoff between marketing and bookings.

• Implement upselling and cross-selling strategies, ensuring that additional services (car rentals, chefs, yacht rentals, etc.) are offered and sold to clients.

• Track and optimize conversion rates, working towards improving the lead-to-booking process.

• Monitor market trends and adjust booking strategies to ensure we remain competitive and innovative.

Process & Tool Development

• Build scalable systems and processes that improve the overall efficiency of the booking department.

• Drive the adoption of new tools and technologies, ensuring the team is equipped to handle growth and complexity.

• Set up real-time reporting and dashboards to track team performance, conversion rates and other key metrics.

Qualifications & Experience

• 5+ years of experience in customer service, sales or bookings, preferably in (luxury) travel, hospitality or a similar industry.

• 2+ years of leadership experience, managing teams with a focus on performance and growth.

• Proven track record of improving processes, implementing tools and managing commercial and operational excellence. • Strong understanding of customer service principles and best practices, ideally within the (luxury) travel segment.

• Hands-on experience in managing booking/customer service flows, responding to client inquiries and converting leads into bookings.

• Familiarity with booking tools, CRM systems and communication hubs (e.g., Helpscout, HubSpot or similar).

• Excellent communication and interpersonal skills, with the ability to inspire and motivate a growing team.

Key Competencies

• Leadership: Ability to manage and grow a team, offering coaching, feedback and setting a high bar for performance.

• Operational Savvy: Proven track record in setting up processes and implementing tools to optimize the efficiency and performance of a team.

• Customer-Centric: A passion for delivering outstanding customer service and ensuring every booking is flawless from start to finish.

• Sales-Driven: Ability to convert leads into bookings and encourage upselling and cross-selling of additional services.

• Problem-Solving: Creative thinker with the ability to anticipate challenges and implement proactive solutions.

• Adaptability: Comfortable working in a fast-paced environment with the ability to manage multiple priorities.

Why Join Us?

• Be a part of a rapidly growing company with ambitious growth plans.

• Opportunity to shape and build the Bookings Department from the ground up.

• Work with a dynamic, passionate team in the luxury travel sector.

• Flexible work environment with opportunities for growth and development.

How to Apply:

If you are a dynamic, hands-on leader with a passion for customer service and operational excellence, we would love to hear from you! Please send your CV and a brief cover letter outlining your experience and why you’re the perfect fit for this role to boris@oneofakindtravel.com.

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