Self-Guided Support Staff (Part-Time)

What to Expect

You’ll support guests from around the world throughout their self-guided cycling tours, both in person and remotely. Depending on the assignment, you may be setting up riders at the start of their tour, transferring luggage between hotels, monitoring riders remotely, answering questions through WhatsApp, or providing emergency pickup support.

This role involves a lot of independent work and driving between locations, primarily in Gunma, Tochigi, and Nagano. Some days are busy and guest-facing, while others involve being stationed remotely and available if riders need assistance.

Your Mission 

Give every self-guided guest a smooth, well-supported cycling experience by setting them up for success, staying one step ahead of their needs, and providing reliable support from start to finish.

What Success Looks Like

• Set riders up for success. Provide a welcoming and professional tour setup, make bike fit adjustments, and ensure guests understand their navigation tools, support systems, tour logistics, and what to expect during their tour.
• Provide reliable and proactive on-call support. Respond promptly and accurately to guest questions, monitor rider progress, independently solve routine problems using Rindo's resources, and know when to ask for help / escalate.
• Handle tour logistics independently. Complete assigned prep, luggage transfers, and other SG tasks accurately and on schedule, following Rindo SOPs and keeping the wider team informed without needing constant direction.
• Be ready when something goes wrong. Stay within the required response area while on emergency support, respond quickly when called, prioritize guest safety, and communicate calmly with guests, Rindo staff, and emergency responders when needed.

Required Skills & Qualifications

• Bike mechanics: Comfortable with basic bike fitting and maintenance, including changing tires / tubes, adjusting brakes and shifting, swapping stems or pedals, and adjusting saddles and seat height.
• Driving in Japan: Holds a valid Japanese driver's license and is comfortable driving 1–3 hours at a time, occasionally totaling 4–6 hours on longer days.
• Language skills:
  • Excellent English communication skills (all guests are English-speaking).
  • Basic Japanese ability to communicate with hotels, restaurants, local businesses, and emergency responders when needed.
• Physical fitness: Able to lift 20–30 kg of luggage and load / unload a ~15 kg e-bike onto a car roof, requiring lifting overhead.
• Independent work: Comfortable working alone, traveling between locations, using company resources to solve problems independently, and being on call for several consecutive days.
• Technology: Comfortable using smartphones, Google Maps, WhatsApp, cycling GPS / navigation tools, and online company resources.

This Role May Not Be a Good Fit If...

• You need a predictable daily routine. Tour locations, responsibilities, and logistics change frequently depending on where guests are riding and what support is needed.
• You have fixed commitments during your on-call day. You may have significant downtime, but you need to remain available to respond if a guest needs assistance or an emergency pickup.
• You need constant direction from a supervisor. Much of the role is performed independently, and you'll need to use Rindo's systems and your own judgment to solve routine problems.
• You aren't comfortable spending significant time working alone. You may be stationed remotely for several days with limited direct interaction with other Rindo staff.
• You don't have a service mindset. Even when you're working behind the scenes, your decisions, communication, and willingness to help directly affect the guest experience.

Season & Availability

We operate two main cycling seasons each year—spring and fall—with a several-month off-season in between. Our self-guided schedule varies throughout the season, but ideally support staff can help with multiple tours per week and remain on call for 5–6 consecutive days in one to two remote locations.

• Spring Season: Early March to mid-June — typically 30+ self-guided tours
• Fall Season: September to early December — typically 40+ self-guided tours

Training & Support

New Self-Guided Support staff receive hands-on training before working fully independently.

• Initial Training: 1–2 days at our Kiryu warehouse learning the role, equipment, SG systems, SOPs, and pre / post-tour logistics.
• Trial Setups: Join an experienced SG staff member for your first two guest setups, gradually taking responsibility for different parts of the process.
• Independent Training: Complete approximately 3–10 setups independently with an experienced staff member available nearby for backup when needed.

We don't expect you to know our systems from day one, but we do expect you to ask questions, learn quickly, and become increasingly independent as you gain experience.

Why Work in Self-Guided Support?

You'll help cyclists from around the world confidently explore rural Japan on their own while working independently across some of our favorite cycling regions.

This role can also offer significant downtime on quieter on-call days. It's a particularly good fit for flexible workers who have remote / computer-based work they can do while stationed in an area, provided that work can be immediately put aside if a guest needs support.

For the right person, it's a flexible way to combine independent work, travel around rural Japan, problem-solving, and guest service.

Compensation

Self-Guided Support is paid at a fixed daily rate based on the type of work being performed and level of guest responsibility.

For every 16 days worked in a single season, support staff members are eligible for a ¥15,000 bonus as an added reward for their time, commitment, and support. 

Tour Accommodations: Rindo covers the cost of all accommodations during tours, including prep and drive days. If a staff requests a room change for personal reasons, any additional accommodation costs will be the guide’s responsibility.

Meal & Transportation Compensation: When working remotely, support staff receive a food allowance of ¥4,000 per day. If our support staff use their own cars for Rindo work, any gas & toll-road fees will be reimbursed.