Brand & Product Designer

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, 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 design our web and mobile apps and our brand. The area we need most in the immediate future is the discovery and booking experience, but there is plenty of work on the core planner too, on both mobile and web. We are also expanding our marketing site, so you would be deeply involved in that.

Design does a lot of the heavy lifting on whether people book with us, so this role has a direct line to the business.

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:

Product Design & Research

• Spend the majority of your time designing and conducting UX research, not on admin work. If you are not talking to or observing users every week, you are doing it wrong
• Proactively find the design problems that are stopping us from reaching our goals, and come up with solutions for them
• Research, design, and develop user interfaces and experiences, independently and collaboratively
• Conduct user research, interviews, and usability testing
• Create wireframes, prototypes, and high-fidelity mockups that fit both the brand and the user

Conversion & The Booking Path

• Own conversion design across the funnel, from the marketing site through to checkout
• Design the core planner experience on both web and mobile
• Use analytics to inform and validate design decisions, and follow through on what they say
• Follow lean product development methodology, iterating quickly on feedback and data

Brand

• Own and evolve the Pilot brand across product, marketing site, and social
• Keep design consistent and high quality across all products and platforms
• Develop and maintain our design system and documentation
• Bring marketing insight into design so the whole experience hangs together
• Communicate design thinking simply to the rest of the team
• 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…

Technical Knowledge and Data Analytics

• Understands and can interpret basic data analytics
• Has a general working knowledge of the latest tech, app, and design trends and applies them
• Understands the basics of branding and its role in product development
• Experience using Figma or similar tools

Product Development and Methodology

• Follows lean product methodology and adapts to a fast product development process
• Stays focused in a fast-paced environment
• Knows how to balance which details to obsess over versus when to move fast

AI & Emerging Tech

• Experience incorporating AI tools to speed up the design process
• Accountable for the quality and reliability of AI-assisted design. Does not blindly hand off without ownership and thoughtful consideration

Empathy and User Interaction

• Has a good understanding of human psychology and a strong sense of empathy, and can see through a customer frustration to the solution underneath
• Highly empathetic and not afraid to be frequently talking to users, both in person and online

Collaboration & Communication

• Can convey complex topics simply
• Excellent verbal and written communication skills
• Able to communicate well with engineers

Independent and Collaborative Work

• Able to think, work, and learn independently, but also a team player who collaborates well
• Self-reliant and able to drive themselves forward without relying on management
• Able to decompose complex problems into manageable units of work

Design Expertise & Background

• Very curious, loves learning, and does it in their spare time
• Understands and expresses brand through product choices
• Critical and opinionated in their design
• Pays great attention to detail, especially in design and critical thinking
• Bachelor's or Master's degree in Design or a related discipline, or a portfolio that makes the question irrelevant
• Loves travel and is an experienced traveler
• 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!! 🙋‍♂️