Updated April 13th, 2024

Job Title: Trip Leader

Company: The Cycling House

About Us: At The Cycling House, we’ve curated exceptional cycling experiences since 2005. Our passion for a great ride and our commitment to service ensures that each trip is unforgettable for our guests. We’re seeking a dynamic and dedicated Trip Leader to join our team and lead our cycling excursions.

Role Overview: Every Cycling House team member goes above and beyond. We pay attention to the smallest details, treat guests like family, and cover many miles by bike with our guests. This job is not easy, and it’s not for everyone, but the challenges are always worth the rewards.

The Trip Leader at The Cycling House is a pivotal role, responsible for creating and delivering the ultimate cycling experience. As the leader for both guests and staff, you’ll be entrusted with making critical decisions, fostering a sense of community, and ensuring the safety and enjoyment of all participants. We are looking for leaders who can do a world-class job with style, professionalism, and a fun-loving attitude.

Key Responsibilities:

• Execute and own the trip plan, delivering an experience that exceeds guests’ expectations while adhering to company values.
• Serve as the primary point of contact for guests, providing exceptional customer service and ensuring their needs are met throughout the trip.
• Manage the on-site team of guides and chefs, providing support, guidance, and feedback to ensure a seamless and meaningful experience for all.
• Adapt trip itineraries as needed due to weather or unforeseen events, maintaining flexibility while upholding the quality of the experience.
• Foster a sense of camaraderie and connection among guests and staff, embodying The Cycling House ethos of hospitality and inclusivity.
• Handle day-to-day operations, including logistics, guest relations, and team management, with professionalism and attention to detail.

Required Qualifications:

• Warm and engaging personality with a natural ability to connect with individuals and build group rapport.
• Strong leadership skills, with the ability to make decisions confidently and assertively, particularly in high-pressure situations.
• Exceptional organizational and time management abilities, capable of managing multiple tasks simultaneously.
• Adaptability and flexibility to thrive in a dynamic, fast-paced environment with ever-changing circumstances.
• Excellent verbal and written communication skills, with a keen attention to guest and team needs.
• Comfort and experience with delivering information concisely and clearly while talking in front of a group.
• Ability to ride a bike on road and gravel surfaces for up to 8 hours while maintaining energy levels and attending to personal needs.
• Valid driver’s license and clean driving record.
  • Europe: Must be proficient in driving a manual transmission. 
• Must be 25 years of age or older due to insurance requirements.

Preferred Qualifications:

• First aid and CPR certification (WFA or WFR is a bonus)
• Previous experience in hospitality, outdoor adventure, or group travel preferred.
• Basic bike maintenance and mechanic knowledge – i.e., changing a flat, swapping stems, applying bike measurements, etc. 

Estimated Travel and Time Commitments:

• Expect to be on the road for 15-20 week-long trips per year, totaling approximately 100-170 workdays per calendar year.
• This includes travel, administrative work before and after trips, and communication with our office throughout the year.

Compensation at a Glance:

• Four weeks of paid training.  New hires transition from guide to co-leader before assuming the role of Trip Leader, with a daily rate of $100 during training.
• Competitive wages for future trips worked are estimated to yield annual earnings of $30,000 – $50,000+, including tips, depending on the number of trips worked. 
• Healthcare benefits
• Cell phone stipend
• All food, lodging, and travel expenses are covered while working trips.
• Access to industry pro deals with leading cycling and outdoor brands.
• Annual 4-day destination staff retreat to connect with colleagues and build lasting friendships.

Equal Opportunity Employer:

The Cycling House is an equal-opportunity employer and values diversity in the workplace. We encourage individuals from all backgrounds to apply.

How to Apply:

If you’re ready to embark on an adventure with The Cycling House and possess the passion, leadership, and dedication to deliver extraordinary cycling experiences, we want to hear from you! Please fill out the application form below for the full-time Trip Leader position.