Product & Brand Designer - for Consumer Travel App Startup

Product & Brand Designer

**Ideal start date is ASAP - role will be closed once a suitable candidate is found**

$40k – $65k CAD • 0.1% – 0.3% ($25k-$75k in equity based on latest valuation)

Hybrid role based in Vancouver, flexible full time. Compensation (cash/equity per year) based on experience: All equity granted via stock options with standard vesting periods. Most recent equity valuation was $18mil USD.

Hey, Hi, Hello!

My name is Connor Wilson. I’m the Founder and CEO of Pilot. 

We’re a travel app company with the mission of helping people like you around the world have an awesome time and make memories offline, so you and others can live a happier, more fulfilling life. 

But before I talk about us, I want to talk about you.

If you’re reading this job description, you’re probably either exploring new challenges or simply curious about a better fit… 

…because whether you realize it or not, you’re not as happy as you could be. 

There could be a lot of reasons for this. Here’s a few:

• You’re overworked and/or underappreciated
• You lack faith, trust or closeness to your colleagues or leaders
• Your company is bureaucratic, lacks transparency, or makes siloed top-down decisions
• You lack autonomy, freedom, or potential for growth
• You’re bored, aren’t learning or being challenged, or don’t care about what you’re working on or what your company does or who it serves
• Your company has an unhealthy/undesirable culture

We’ve been there. 

I’m here to tell you it doesn’t have to be that way. 

You know it doesn’t. 

Remember that project back in school or earlier in your life/career that you really enjoyed or got super passionate about? That didn’t feel like work did it? It was fun. Well your job shouldn’t either. Especially considering we spend most of our lives at our jobs.

Is your current company going to give you that?

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://docs.google.com/document/d/1gadFcFo79JWtVyI7n1FMj4wYePfzirAvZ1_kS7d2WnQ/edit?tab=t.0

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 get compensated competitively 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 - 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 & solve them, and are pretty experienced. You can learn more about me here: https://www.connorjwilson.com. TL’DR: this isn’t my first startup; my last tech startup sold for 8-figures after we grew it for 3 years without investors, reaching $3.5 million in annual recurring revenue. 
• Decisions based on data, not based on that Linkedin post your manager saw that one time. Everyone at any 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. 
• 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  

“Okay, but what even is Pilot?”

Great question. Glad you asked.

We’re building Pilot to be a Collaborative Travel Hub, powered by AI, to help groups (of 2 or more) discover, plan, book, and share experiences with the people they care about. A shareable platform like Notion or Google Docs with social functionality, not a social network. 

• We’re a Next Canada Accelerated Startup. That’s this: nextcanada.com 
• We incorporated on Sixto de Mayo 2020. We missed Cinco de Mayo by one day and are still bitter about it. We spent the time since then iterating towards our current platform. It wasn’t until 2022 that we had a team of full-time staff, as I had to work at the acquirer of my previous company after the sale for a bit.
• We’ve raised over $2M to date
• Today we’re a team of 10.
• Our product is live publicly (try it at pilotplans.com) - we started with our trip planner, and have been building out the “explore” and bookings side of the app for the last year or so.
• Over 30,000 people have signed up to Pilot
• And it seems to be working! After 10 minutes of planning, 60% of people say they’d never go back to their old way. Activation and retention rates are 2-3x the travel industry average.
• We’re growing fast: we recently became a certified Google Travel Partner to distribute 2M+ stays. If we can pull it off, that means millions a year in annual revenue. We’ve got a clear path to this high level of distribution, something most startups struggle to ever find.

So that’s us. Feel free to check out the team at pilotplans.com/careers 

The role. The goal.

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

It’s very simple. We want someone to help us design our web and mobile applications and our brand. The areas we most need in the immediate future are improving the conversion rates on our “explore” and booking features but there’s lots of work on our core planner platform as well, both for our mobile and web applications. We’re planning a big expansion of our existing marketing website to promote our services more, so you’ll be deeply involved in that if you join. 

What you’ll be doing and learning

You don’t need to necessarily 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:

• Spend the majority of your time designing and conducting UX research, not on admin work. If you’re not talking to or observing users every week, you’re doing it wrong.
• Proactively seek out and identify problems with existing designs that are preventing us from reaching business goals, e.g. bookings, and come up with design solutions for those problems
• Research, design, and develop user interfaces and experiences independently and collaboratively.
• Simplify and effectively communicate complex design concepts to stakeholders and team members.
• Conduct user research, interviews, and usability testing to understand user needs and gather feedback.
• Stay updated on industry trends, best practices, and emerging technologies to apply them to design solutions.
• Create wireframes, prototypes, and high-fidelity mockups that align with brand guidelines and user needs.
• Ensure design consistency and quality across all products and platforms.
• Develop and maintain design systems and documentation.
• Follow lean product development methodologies, iterating quickly based on user feedback and data.
• Utilize data analytics to inform and validate design decisions.
• Integrate marketing insights into design solutions for cohesive user experiences.

“Should I apply??!??!?”

First of all, obviously. 

That said, the ideal candidate…

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 to apply 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.

AI & Emerging Tech

• Experience incorporating AI tools to expedite the design process.
• Accountable for quality and reliability of AI designs; does not “blindly handoff” without ownership and thoughtful consideration

Empathy and User Interaction

• Has a good understanding of human psychology and a strong sense of empathy.
• Highly empathetic, 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.
• Ability to communicate well with engineers.

Mindset & Soft Skills

• Has a good understanding of human psychology, and a strong sense of empathy, being able to see through customer’s frustration and turn that into solutions.
• Is very curious, who loves learning, and does it in their spare time
• Ability to decompose complex problems into manageable units of work.
• Know how to balance which details to obsess over versus when to move fast.

Independent and Collaborative Work

• Able to think, work, and learn independently, but also a team player who collaborates well with others.
• Self-reliant and able to drive themselves forward without relying on management.
• Enjoys working with others in an open, collaborative manner.

Education and Design Expertise

• Very curious, loves learning, and does it in their spare time.
• Loves travel and is an experienced traveler.
• Passionate about travel and positively impacting the lives of others.
• Bachelor’s or Master’s degree in Design or a related discipline.
• Understands and expresses brand through product choices.
• Critical and opinionated in their design.
• Pays great attention to detail, especially in design and critical thinking.

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

Hope to hear from you soon!!