Group Specialist, Success

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, with unlimited paid vacation (with manager approval/coordination) and competitive pay so you are rewarded for the business you bring in.
• 🙌 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 group bookings end to end, and to win more of them. Retreats, conferences, weddings, sports teams, and larger friend and family trips keep finding us on their own, and we have never had anyone dedicated to them. That is what this role is.

Half the job is looking after the groups that come to us. The other half is going and finding more, through business development and marketing. It is some of the best business we get, and nobody owns it yet. You would.

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:

Drumming Up New Business

• Go and find group business rather than waiting for it to arrive
• Build relationships with the kinds of organisations that travel in groups: companies, clubs, teams, event organisers, wedding planners
• Work with marketing on campaigns, partnerships, and content aimed at group travel
• Follow up with past groups and turn one trip into the next one
• Bring us ideas for where group demand is hiding, then go and get it

Owning Group Requests

• Respond quickly to group, retreat, and wedding block enquiries
• Work out what the group actually needs: dates, size, budget, flexibility, and who makes the call
• Put together options and quotes a group can decide from, not a wall of links
• Follow up until they decide, without being pushy

Sourcing & Holding Inventory

• Source rooms, rates, and holds with hotels and our distribution partners
• Negotiate group rates and terms
• Get confirmed options into Pilot so the group can plan around them
• Keep track of what we are holding and when it expires

Booking & Vendor Operations

• Place bookings, confirm them with the property, and keep good records
• Get on the phone with hotels and partners when that is what resolves it
• Sort out booking errors, availability problems, and special requests
• Handle changes and cancellations all the way through to travel

Support During & After the Trip

• Be reachable when a group is travelling and something goes wrong
• Handle escalations calmly and with urgency
• Make sure people feel informed and taken care of
• Follow up afterwards and turn a good trip into repeat business

Making It a System

• Build the templates, processes, and documentation so the next one is easier
• Flag recurring problems to product and engineering
• Keep an eye on how the pipeline is converting and what it is worth
• 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…

Core Traits and Working Style

• Calm under pressure and emotionally steady, even when a group of 30 needs an answer tonight
• Highly reliable, detail aware, and follows things through to completion
• Acts with urgency and does not let issues linger
• Comfortable working without perfect information and making good judgment calls
• Polite, respectful, and empathetic with guests and partners, while still being firm when needed
• Low ego. Focused on solving the problem, not defending themselves

Business Development and Marketing

• Comfortable generating business, not just servicing it. Happy to go out and find the next group
• Comfortable asking for the business without being pushy
• Can negotiate rates and terms with a hotel and hold a position
• Has ideas about where demand comes from, and is willing to test them
• Motivated by closing and by margin, not just by clearing a queue

Communication and Execution

• Very strong written communication. Clear, concise, and human
• Comfortable getting on the phone with guests, hotels, and partners
• Knows when async is enough and when a call resolves things faster
• Able to explain issues and next steps clearly to non-technical people

Availability and Responsiveness

• Genuinely available on an on-call basis, including some evenings and weekends when a group is travelling
• Comfortable working Pacific time hours for North American groups
• Comfortable with fast-moving environments and shifting priorities
• Understands group travel is time sensitive and that dates expire

Experience and Background

• Prior experience in group sales, hotel sales, events, travel agency work, hospitality, or customer support is strongly preferred
• Experience dealing directly with customers or external partners is a plus
• Travel or hospitality experience is helpful but not required
• Based in or near Vancouver, and able to be with us in person 1 to 3 times a week

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!! 🙋‍♂️