Customer Support & Operations Specialist

Remote, Part-Time (15-25hrs/week), Flexible Contractor - Based in Japan

Monthly Salary of ¥124,000 – ¥165,000

**Ideal start date is ASAP - role will be closed once a suitable candidate is found**

NOTE: Do not apply via whichever website you are seeing this job description. Apply via this link instead:

(see details below)

• Please note that for this application form you will be required to record a video of yourself answering a few questions, so be prepared to do that.

Why work at Pilot

If you think you'd like working at a company whose very purpose is to give you and others the absolute best life possible, in the most fun way possible, working on cool things with cool people, to help people have an awesome time and make memories…

…well then Pilot might just be the place for you.

It's embedded into who we are. That's why we have a public 23-page culture code. Read it here to see if we vibe:

At Pilot you'll get…

• A flexible workweek, with unlimited paid vacation
  (with manager approval/coordination) and get compensated competitively through salary and stock options so you'll own your work.
• Autonomy and freedom.
  As long as our customers are happy and the support inbox is handled, you otherwise mostly get to pick your own projects, set your own goals, and work the hours you want, where you want, with who you want. Our team travels all over the world - you can too.
• Work with people who all want to be your friend
  (we actually hang out). Our team is incredibly talented, but we value humility.
• Leaders who own their mistakes
  (yes, that includes me), actively seek feedback to identify & solve them, and are pretty experienced. You can learn more about me here: TL'DR: this isn't my first startup; my last tech startup sold for 8-figures after we grew it for 3 years without investors, reaching $3.5 million in annual recurring revenue.
• Decisions based on data
  , not based on that Linkedin post your manager saw that one time. Everyone at any every level is empowered to make decisions because we share everything and have a culture of transparency, trust, and experimentation.
• It's travel, so it's super fun. It's a startup, so it's super challenging
  with a huge upside.
  And, it's social impact focused
  , so you'll actually be helping people, not just maximizing profits.
• We're proud to have a diverse team
  , with plans to become a B-Corp eventually.
• We also have some great employer reviews
  here:

"Okay, but what even is Pilot?"

Great question. Glad you asked.

We're building Pilot to be a Collaborative Trip Booking and Planning App, powered by AI, to help groups (of 2 or more) discover, plan, book, and share experiences with the people they care about. A shareable productivity tool like Notion or Google Docs but for planning and booking trips.

• We've been featured by the Washington Post, WIRED Magazine, Forbes, and TechCrunch, and are a Next Canada Accelerated Startup. That's this:
• We incorporated on Sixto de Mayo 2020. We missed Cinco de Mayo by one day and are still bitter about it. We spent the time since then iterating towards our current platform. It wasn't until 2022 that we had a team of full-time staff, as I had to work at the acquirer of my previous company after the sale for a bit.
• We've raised over $2.2M CAD to date
• Today we're a team of ~10. Check out the team at
• Our product is live publicly (try it at ) - we started with our trip planner, and have been building out the "explore" and bookings side of the app for the last year or so.
• Over 40,000 people have signed up to Pilot
• And it seems to be working After 10 minutes of planning, 60% of people say they'd never go back to their old way. Activation and retention rates are 2-3x the travel industry average.
• We're growing fast
  : we recently became a certified Google Travel Partner to distribute 3M+ stays. If we can pull it off, that means millions a year in annual revenue.
  We're already doing thousands of dollars in bookings every day
• which is what we need this role for So, we've got a clear path to this high level of distribution, something most startups struggle to ever find.

So that's us. Feel free to learn more about us at:

The role. The goal.

Here's what we're looking for from you:

It's very simple. We want someone to
run all our customer support operations, including helping with managing travel bookings for users, and supporting executives in partnerships relating to them.

We're still small, but we're quickly ramping up and need someone to own this to allow us to do so.

What you'll be doing and learning

You don't need to necessarily already have experience doing these (but it helps), and they are entirely subject to change based on what gets the most results. But here goes. The job duties are:

Customer Support Ownership

• Own customer support end to end across chat, email, and phone calls
• Respond quickly, clearly, and calmly to user issues and questions
• Handle escalations and time-sensitive cases with urgency and judgment
• Decide when to move a conversation from async to phone to resolve faster
• Ensure users feel informed, respected, and taken care of

Proactive Support & Engagement

• Set up and maintain saved replies, macros, and support workflows
• Identify repeat issues and confusing flows and flag them to product and engineering
• Proactively reach out to users when bookings or trips look risky or unclear
• Improve help docs, internal notes, and canned responses to prevent future tickets
• Treat support as a system to improve, not just a queue to clear

Booking & Vendor Operations

• Call hotels and travel partners to confirm bookings after they are placed.
• All bookings should be made instantly automatically, but we call to make sure.
• Resolve booking errors, availability issues, and special requests directly with vendors
• Follow up persistently until confirmations are received and documented
• Communicate clearly with users when issues arise and explain next steps
• Keep accurate internal records of booking confirmations and vendor outcomes

Partner & Ops Support

• Assist with operational and admin tasks related to partnerships and suppliers
• Coordinate follow-ups, confirmations, and light documentation for deals
• Act as a reliable point of contact between Pilot and external partners
• Help ensure partner communications are timely and organized

Continuous Improvement

• Spot patterns across support, bookings, and vendors and suggest process fixes
• Help define and improve internal SOPs for support and booking operations
• Share clear, actionable feedback with the product team based on real user issues
• Take ownership of problems until they are fully resolved, not just replied to
• Anything else as needed. We're a startup, so this is subject to change

Administrative Assistance

• When not busy with the above, you will be helping free up executive time with various miscellaneous administrative assistance tasks, such as those relating to: inbox management, partner research, recruitment, and others. However, your primary responsibility is customer support and any operational work needed to provide a smooth customer experience.

You'll need to be eager, ready to work hard, and able to work independently. We're moving fast, and that means doing a lot more in less time, sometimes cutting corners to do so.

Still, work-life harmony is important so you'll be the one setting your own goals to make sure they can be reasonably accomplished during your working hours.

The ideal candidate probably has at least some of these traits…

Core Traits and Working Style

• Calm under pressure and emotionally steady, even in stressful or time-sensitive situations
• Highly reliable, detail aware, and follows things through to completion
• Acts with urgency and does not let issues linger
• Proactive by default. Fixes problems at the root and prevents repeats
• Comfortable working without perfect information and making good judgment calls
• Polite, respectful, and empathetic with users and partners, while still being firm when needed
• Low ego. Focused on solving the problem, not defending themselves

Communication and Execution

• Very strong written communication. Clear, concise, and human
• Comfortable getting on the phone with users, hotels, and partners when needed
• Knows when async is enough and when a call will resolve things faster
• Able to explain issues and next steps clearly to non-technical users
• Can handle sensitive or emotional customer situations calmly

Independence and Learning

• Able to work independently and manage their own priorities day to day
• Learns quickly and enjoys figuring things out without hand-holding
• Curious and self-driven. Regularly learns new tools, systems, or concepts on their own
• Comfortable picking up basic technical concepts and learning light coding or scripting if helpful

Systems and Improvement Mindset

• Thinks in systems, not just tasks or tickets
• Notices patterns across support, bookings, and operations
• Comfortable working with basic data, metrics, and logs to understand issues
• Willing to help improve workflows, templates, documentation, and internal processes

Availability and Responsiveness

• Very online and responsive during working hours
• Comfortable with fast-moving environments and shifting priorities
• Understands that customer support and booking operations can be time sensitive

Experience and Background

• Prior experience in customer service, support, hospitality, retail, or operations is strongly preferred
• Experience dealing directly with customers or external partners is a plus
• Travel or hospitality experience is helpful but not required

If you meet even 50-70% of these you could be a great fit