Cycling Tour Guide

Seasonal Cycling Tour Guide Rindo Bike Tour Japan is a small cycling tour company based in Kiryu, Gunma, specializing in high-end, multi-day cycling adventures through the rural backroads of Japan. We're looking for cyclists with a strong service mindset to join our seasonal guide team. This isn't simply a job for people who love riding bikes—our guides are responsible for creating an exceptional experience for guests from around the world, both on and off the bike. For us, your mindset and personality matter more than how many miles you've done on the bike. We'll favor candidates who are a great culture fit and eager to grow into the role over highly experienced cyclists who aren't the right fit for our team. Your Mission Give every guest a 5+ star cycling experience in Japan by guiding them safely and confidently, connecting them with the culture and stories of the places they ride through, while working closely with a team of fellow A-player guides. What Success Looks Like - Guide confidently and safely. Come prepared, know the day's route and stops, adapt to different rider abilities, and help every guest complete the day's ride safely. - Create a 5+ star guest experience. Bring a genuine service mindset, build connections with guests, and look for ways to make their experience exceptional. - Bring Japan to life. Share your knowledge of Japanese culture and the stories behind the places we visit. - Be someone the team can rely on. Communicate well, follow changing tour logistics, work independently, and step in to help when needed. This Role May Not Be a Good Fit If... - You love cycling but don't enjoy service work—the job is about the guests' ride, not your own. - You need a predictable, recurring schedule or struggle with frequently changing logistics. - You prefer clear instructions for every task rather than problem-solving independently. - You want to experience the tour like a guest. The rides, meals, ryokans, and cultural experiences are part of the job, but you're there to create that experience for someone else. - You prefer work where your guest-facing responsibilities end at a set time. Guiding extends beyond the ride itself to meals, transfers, cultural stops, and other shared parts of the tour. Compensation & Support - Daily tour pay ranges from ¥20,000–¥40,000, increasing as guides complete more tours with Rindo. Guides are also eligible for a ¥15,000 bonus for every two tours completed within a single season. - Rindo covers required tour accommodations and provides daily meal allowances during prep, drive, and tour days. - New guides receive pre-tour training and work alongside experienced guides and a Lead Guide on their first tours. Guides who consistently perform at a high level have opportunities to take on greater responsibility and develop into Lead Guide roles. Location & Work Structure - Kiryu, Gunma is our home base. Guides need to travel to our warehouse in Kiryu for tour preparation and setup. Travel to / from Kiryu is at the guide's own expense; Rindo covers required travel during the tour itself. - Free seasonal guide housing is available in Kiryu. Guides can stay in shared company housing during the season, including between assigned tours. - Tours are multi-day assignments. Guides who commit to several back-to-back tours may choose to base themselves in Kiryu for much of the season, returning home during the 3–4 day gaps between tours. For example, a guide working 4–5 consecutive tours could expect to spend roughly two months based primarily in Kiryu. - Seasonal guides work on a fixed-rate contractor basis, with daily tour pay increasing based on the number of tours completed with Rindo. Why Guide With Rindo? You'll ride some of our favorite roads in rural Japan, work alongside a small team of experienced guides, and build genuine connections with cyclists from around the world. It's demanding work, but for the right person, it's an opportunity to combine cycling, service, travel, and Japan in a way few jobs offer.