Supply Ops Growth

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 4 day workweek if you complete your full-time work before Friday, with unlimited paid vacation (with manager approval/coordination), and competitive pay through salary and stock options so you’ll own your work.
• 🙌 Near total autonomy and freedom. You 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, 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. This is a growth role, pointed at supply. We want someone to grow the inventory we can sell, get more of it live and bookable, and keep our pricing sharp enough to win the booking. We have contracted a lot more inventory than we currently distribute, and closing that gap is one of the biggest levers we have.

We are hiring in Palma because it puts you inside one of Europe’s densest hotel markets and within easy reach of the rest of it, but the role covers our supply everywhere, not only Europe. This is slow, relationship-driven work that most startups never get right, and we are already further along it than most.

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:

Getting Our Supply Live & Selling

• Get more of our contracted inventory live and bookable
• Improve how much of the available demand we can answer with live rates
• Work with engineering on the systems that deliver pricing at scale
• Audit rates, availability, and content quality so what we show is right

Pricing & Competitiveness

• Own how we price against competitors, and keep testing it
• Find where we are losing on price or coverage, and fix it
• Balance margin against volume, and know which one we need right now
• Bring us the pricing strategies we have not tried yet

Winning New Supply

• Source, pitch, and close direct hotel and supplier relationships, in person where it matters
• Negotiate rates, terms, and inventory access
• Attend industry events and trade shows, and come back with signed relationships rather than business cards
• Build the pipeline and keep it honest

Making It Repeatable

• Build the process, templates, and playbook so supply work scales past just you
• Track coverage, conversion, and margin by market, and act on it
• Work alongside our advisor, who has built this kind of supply operation before at a much larger scale
• 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…

Domain

• Experience in travel supply, hotel distribution, connectivity, revenue management, partnerships, or B2B sales in travel is strongly preferred
• Understands, or can learn very fast, how bed banks, channel managers, connectivity providers, and rate parity actually work
• Comfortable with the idea that travel supply is still a handshake business won in person over time
• Existing relationships in European hotel markets are a significant plus

Language & Location

• Fluent English, written and spoken. Our whole team works in English day to day
• Spanish is a strong plus, and other European languages help
• Based in or near Palma de Mallorca, with the right to work in Spain
• Able to travel frequently across Europe

Growth and Pricing Instinct

• Thinks like a growth person. Supply is the lever, but the goal is more bookings
• Comfortable owning a pricing strategy and iterating on it with data
• Understands margin, not just volume, and can tell when a deal is bad
• Comfortable in spreadsheets. You will live inside coverage, pricing, and margin numbers
• Can work with engineers on integrations without needing to be an engineer

Closing & Working Style

• Comfortable negotiating and closing, and happy to do it face to face
• Organized, follows up persistently, and does not let a deal go quiet
• Able to work independently and manage their own priorities day to day
• Comfortable with meaningful overlap with Pacific time a couple of days a week
• Low ego. Focused on solving the problem, not defending themselves
• Loves travel and has done a lot of it

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!! 🙋‍♂️