Finance & Internal Ops

Why you should 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: https://bit.ly/3KmavZF

At Pilot you’ll get…

• 🌴 A flexible schedule you set yourself, with unlimited paid vacation (with manager approval/coordination) and competitive pay, plus stock options so you own a piece of your work.
• 🙌 Near total autonomy and freedom. You pick your own projects, set your own goals, and work the hours you want, with who you want. Other than the days we get together in person, you work wherever you like. Our team travels all over the world, and 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 and solve them, and are pretty experienced. You can learn more about me at connorjwilson.com. TL’DR: this isn’t my first startup. My last one, NiceJob, sold for $30M in 2021 after we grew it for 3 years without investors, reaching $3.5M in annual recurring revenue.
• 🧪 Decisions based on data, not based on that LinkedIn post your manager saw that one time. Everyone at 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.
• 🧳 Paid travel on occasion, for training and research. So far we’ve paid for team trips to and around Thailand, Taiwan, Colombia, Portugal, Spain, Hungary, Turkey, India, San Francisco, Vancouver, Toronto, and more. These have been very valuable for the team and we’ll keep doing them.
• 🌎 We’re proud to have a diverse team, with plans to become a B-Corp eventually.
• ⭐ We also have some great employer reviews here: glassdoor.ca/Reviews/Pilot-Reviews-E3311415.htm

Reviews and culture code: Glassdoor | Culture code | About Connor

“Okay, but what even is Pilot?” 🤔

Great question. Glad you asked.

Pilot is multiplayer consumer AI for travel: the free web & mobile app where groups plan, decide, & book trips together.

Think Notion or Google Docs, but purpose-built for travel, and simple enough that anyone can use it. More visual and interactive than a chatbot. It stays free because we make our money on the booking, not on paywalling the planning.

• 🎓 We’ve been featured by The Washington Post, WIRED, Forbes, and TechCrunch. We’re Next Canada and Creative Destruction Lab alumni, were selected for TechCrunch’s Startup Battlefield 200, were a New Ventures BC top 10 startup in 2023, and a BC Tech top 3 startup of the year in 2024.
• 💸 We’ve raised about CA$2.2M to date, from funds and from angels including the founders of Moment Energy, Nexonia, Farewill, and DayOne, plus an AI engineering leader at Meta.
• 😎 Today we’re a team of about 10, led by people who all ship code daily and talk to customers weekly. Check out the team at pilotplans.com/careers
• 🏆 Our product is live (try it at pilotplans.com). We started with the free trip planner, and now we book too, as merchant of record across 3.2 million stays.
• 🎉 Over 120,000 travelers have used Pilot to help book and plan their trips
• ⌚ And it seems to be working. After 10 minutes of planning, 60% of users say they’d be very disappointed to lose Pilot, against a 40% benchmark for product-market fit. People who book come back at 50% after 90 days, close to 3x the travel industry average. We’re rated 4.4 on Trustpilot. Most big OTAs sit under 2.
• 🚀 We’re growing fast. We went from near-zero to a $1.2M gross-booking run rate in six months, on $10,500 of ad spend. We’re live on Google Travel, which is distribution usually reserved for much later-stage companies, and we’ve signed Skyscanner, Viator, GetYourGuide, Tiqets, Omio, Enterprise, and Faye.
• 🧮 We’re also unusually efficient. Net burn averaged about $14,600 a month in the first half of 2026, roughly 80% below typical for our stage, with a burn multiple of 0.83. Under 1 is top decile. That means new money goes to growth, not survival.

So that’s us. Feel free to learn more about us at: pilotplans.com/careers

The role. The goal. 🛣️

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

It is very simple. We want someone to own the money, and the machinery behind it. We sell travel directly, so real cash moves through us every day: guests pay us, we pay suppliers, and the details in between matter. Beyond that, somebody needs to own the internal operations that keep a company running. Right now the founders handle all of it, and that does not scale.

This role starts hands-on and grows fast. It is a high trust seat, and we would rather bring in someone early in their career who is sharp and reliable and let them grow into running finance and operations here, than hire someone senior who wants to stay in their lane. The pay and the equity are set up for exactly that.

What you’ll be doing and learning 🧑‍💻

You don’t necessarily need to 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:

Money In, Money Out

• Own the booking money flow end to end: payments in, supplier payments out, refunds, and chargebacks
• Reconcile bookings against supplier invoices and payment settlements
• Pay invoices and handle the recurring operational work that keeps things moving
• Look after our cash so it is working for us while we hold it

Local Payment Registration

• Own the project of getting Pilot registered in the places we need to be, so we can access local payment processing rates
• Work through the requirements, paperwork, and providers in each locality
• Cut how much margin we hand over to payment processing, which is one of our larger costs
• See it through. This is a long project and it would be yours

Margin & Cost Efficiency

• Track real margin per booking, after all the costs that eat into it
• Find where fees, currency conversion, and supplier terms are quietly costing us
• Look for savings everywhere, not just in finance: software, IT spend, subscriptions, vendors
• Approve smaller expenses and manage our tooling and IT spend
• Cut what we do not need

Planning, Reporting & Controls

• Own financial planning: budgets, forecasts, and what we can afford to do next
• Own the monthly close, bookkeeping, and management reporting
• Keep the numbers the team and our investors see accurate and current
• Build simple controls so mistakes get caught before they get expensive
• Support our annual R&D tax credit claim, and the data room when we raise

Internal & People Ops

• Own HR operations until we hire someone dedicated to it: onboarding, contracts, payroll, and the admin around hiring
• Keep us clean on tax, filings, and employment requirements across the countries we hire in
• Be the person who makes internal things work, so nobody else has to think about them
• Anything else as needed. We are a startup, so this is subject to change!

One important thing about all of the above

Treat everything above as a starting point, not a job spec carved in stone. It is not exhaustive, and it will change.

We’re a startup. We do more of what works and less of what doesn’t, and that means the shape of this role will move as we learn, sometimes quickly. You’ll pick up things that aren’t on this list, and some of what is on this list will turn out not to matter. So you need to be genuinely adaptable, and ideally you should enjoy that rather than just tolerate it. If what you want is a fixed list of duties that stays fixed, this won’t be the job for you, and that’s okay.

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.

“Should I apply??!??!?” 🤯

First of all, obviously.

It’s easy, and you can do it here: https://forms.gle/D1HrBVbDteJqXwZYA

Second of all, as long as you think you have either the necessary skills, or the ability to learn them very quickly to do this role, you’re good. We care about your ability to execute, not your experience, though it certainly can be an indicator.

That said, the ideal candidate probably has these traits…

Experience and Background

• 5+ years in finance, accounting, or finance operations, ideally with startup experience
• CPA, or working toward it, is a plus but not required
• Experience with merchant of record, marketplace, or payments reconciliation is a big plus
• Experience with Canadian SR&ED claims is a strong plus
• Multi-currency experience

Craft

• Very comfortable in spreadsheets, and in an accounting system such as Xero or QuickBooks
• Detail obsessed. Numbers either tie out or they do not
• Comfortable building a simple process where none exists today
• Comfortable picking up new tools and light automation if it saves hours

Ownership and Working Style

• Can own a long, unglamorous project end to end without being chased. The payment registration work is exactly that
• Able to work independently and set your own priorities
• Can explain a number to a non-finance person without condescension
• Discreet with sensitive information. You would see payroll and everything else
• Comfortable picking up HR and internal operations alongside the finance work
• Acts with urgency and does not let issues linger
• Low ego. Focused on solving the problem, not defending themselves

Fit

• Based in or near Vancouver, and able to be with us in person 1 to 3 times a week
• Comfortable with a part-time arrangement that may grow into something bigger
• Very curious, loves learning, and does it in their spare time
• Loves travel and is an experienced traveler

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

“I’m Interested, now what?” ⏭️

Wherever this job is posted (be it Wellfound, LinkedIn, Indeed, or some other site), submit your application here instead: https://forms.gle/D1HrBVbDteJqXwZYA. Other sites are not checked.

This form replaces the need for a screening call, so we can move straight to a proper interview if you’re selected.

From there it’s short: a role-specific interview with the people you’d work with, then a conversation with me plus a reference check.

Feel free to slide into our DMs with any questions.

Hope to hear from you soon!! 🙋‍♂️