Content Intern, Creators

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 that works around your class schedule, with unlimited paid vacation (with manager approval/coordination) and competitive pay for an internship, 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 help us build our creator marketing strategy from scratch. We have never done it. The idea is to get Pilot in front of travel creators’ audiences, paid where it works and organic where we can, and to find out what actually moves the needle. Beyond that it is not defined, which is rather the point.

This is a blank page with a budget behind it, not a list of tasks. If you want a role where you find out whether something works, rather than execute someone else’s plan, this is that one.

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:

Building the Strategy

• Work out which creators, platforms, and formats are worth our money and our attention
• Build the case for what to test first, then go and test it
• Figure out what a good deal with a creator looks like for us, and what a bad one looks like
• Bring a point of view. Nobody here has done this before either

Running Creator Campaigns

• Find and reach out to travel creators whose audience looks like our users
• Negotiate and manage paid placements, sponsorships, and collaborations
• Brief creators well enough that what they make actually works
• Chase organic and earned coverage wherever we can get it without paying for it

Measuring What Works

• Track what each creator and each campaign actually brings in
• Be honest about what did not work, and say so early
• Report back regularly with numbers rather than vibes
• Double down on the formats and the creators that perform

Feeding the Rest of the Funnel

• Repurpose creator content across our own channels
• Work with the growth team so creator activity feeds everything else we are doing
• Use AI tools to move faster without letting quality slip
• 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…

Commercial Instinct

• Curious about what makes people buy, not just what makes them watch
• Comfortable with numbers, and can work out whether a campaign paid for itself
• Willing to call something a failure quickly rather than defending it
• Has opinions about which creators are worth it and which are inflated

Outreach and Negotiation

• Not afraid to send the cold email, or the follow-up after it
• Handles rejection well. Most creators will say no
• Organised enough to run outreach without being chased
• Can hold a position on price without burning the relationship

Craft and Taste

• Has made content of their own, and can show it
• Writes clearly and quickly, in a human voice
• Comfortable in CapCut, Canva, Figma, or similar
• Can tell the difference between content that performs and content that just looks nice

Professional Fit

• Currently studying or recently finished, in marketing, communications, business, or something adjacent, or self-taught and able to prove it
• Comfortable with a role that is genuinely undefined and will change as we learn
• Based in or near Vancouver, and able to be with us in person 1 to 3 times a week
• Comfortable with intern pay but excited by equity, training, autonomy, and rapid growth if you prove yourself
• Loves travel and has done some 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!! 🙋‍♂️