Dream Job? We are looking for a trip leader.

The Cycling House is searching for a highly motivated, team-oriented trip leader to lead and guide 10-18 week-long trips for our 2022-2023 seasons. The ideal candidate is a natural leader who loves working with people and has a flexible schedule that allows extended travel and time away from home.

The trip leader is one of the most important leadership positions at The Cycling House. They are the leader for both TCH guests and staff, the one who makes the final decisions at camp, and the catalyst who helps make the experience unique and memorable. 

The end goal for a trip leader is to run a successful trip that reflects our company’s values. The trip leader’s responsibility is to deliver “The Cycling House Experience” that we’ve been cultivating since 2005. Trip leaders go above and beyond our guests’ expectations – which usually comes out in the small “wows” throughout the week – and have personalities that connect with our guests. The safety of the riders and our staff is the trip leader’s primary concern. Being assertive in critical situations is a must. The trip leader must call the shots and expect staff to execute the plan in serious situations. 

What are the attributes of a successful trip leader?

  • Brings commitment to service – working with the team to make the week unforgettable for each guest.
  • Has a warm personality that connects easily with individuals and brings groups together. Can show up as the ultimate storyteller or a thoughtful listener.
  • Attuned to guests’ and team members’ needs.
  • Stays composed under pressure amid guests’ expectations, team members’ needs and unforeseen bumps along the road.
  • Has the confidence to facilitate the overall trip experience and pre-ride and evening briefings with everyone.
  • Has a humble nature and isn’t afraid to tackle a sink full of dishes.
  • Can shift quickly from a relaxed conversation with guests to time-pressed tasks behind the scenes.
  • Has an ownership mindset – takes responsibility for the team and oneself, as well as aims for continuous improvement.
  • Is quick on their feet and uses sound judgment to make decisions as needed, often on the fly, sometimes weighing in with the rest of the team. 

What are the trip leader’s essential responsibilities?

  • #1: Executing and owning the trip plan. The Cycling House has designed and honed a variety of trip itineraries. The trip leader delivers the experience guests signed up for and beyond. The trip leader takes responsibility for executing the trip itinerary, preparing for guests’ arrival on Day One through their departure on Day Seven. The trip leader adapts the itinerary due to weather or other unforeseen events. The trip leader owns day-to-day operations throughout the trip.
  • #2: Serving as the guest relations point person throughout each trip. The trip leader serves as The Cycling House representative with guests and as social coordinator for all guests and staff. The trip leader strives to make each guest feel confident and secure throughout their experience. In anticipation of each trip, the trip leader prepares the team for incoming guests’ needs – dietary restrictions, medical issues and other preferences. Between tasks, the trip leader intentionally connects with each guest. Cyclists love their coffee, and the trip leader often gets it going first thing in the morning. 
  • #3: Managing the trip team of guides and chefs. The trip leader ensures the on-site team is equipped and supported to create a meaningful experience for all guests. The trip leader oversees quality control of food, accommodations and overall experience. The trip leader strikes a balance between encouragement and constructive feedback when needed for team members. The trip leader often turns the lights on to start the day and then off when closing things down for the night.

What are the estimated travel and time commitments?

Expect to be on the road for 12-18 week-long trips per year, a total work commitment of around 80-144 workdays per calendar year (~8 workdays/trip), including any travel, administrative work before and after the trip, and communication with our office spread out over the winter, spring, summer and fall.

What is the compensation package?

Four weeks of paid training. After completing these four weeks, we will implement the trip leader pay as outlined below. During these four training weeks, you will progress from the guide to co-leader before taking the reigns as a trip leader. During the four weeks of training, future trip leaders will get paid $100/day + tips. 

After the four weeks of paid training, trip leaders who advance will be offered a schedule and paid a competitive day rate + tips for future trips worked. Total annual wages are estimated at $19,500 – $35,000+ (Day rate + tips). The exact day rate is TBD after completion of the training process.

The Cycling House pays for all of your food, lodging and travel expenses while working trips. In addition, as a TCH employee, you have access to industry pro deals with Moots, Cervelo, Patagonia and many more companies. We realize this is a lifestyle job, so we plan an annual all-staff retreat, and you will gain a few friends for life.