Pilot
Website:
pilotplans.com
Job details:
Hey, Hi, Hello! š
My name is Connor Wilson. Iām the Founder and CEO of Pilot.
Weāre a travel tech company with the mission of helping people like you around the world discover and share memorable experiences in the real world, so you and others can live a happier, more fulfilling life.
But before I talk about us, I want to talk about you.
If youāre reading this job description, youāre probably either unemployed and need a jobā¦
ā¦or youāre already employed, but for some reason or anotherā¦
ā¦youāre hereā¦
ā¦because whether you realize it or not, youāre not as happy as you could be.
There could be a lot of reasons for this. Hereās a few:
- š© Youāre overworked and/or underappreciated
- š© You lack faith, trust or closeness to your colleagues or leaders
- š© Your company is bureaucratic, lacks transparency, or makes siloed top-down decisions
- š© You lack autonomy, freedom, or potential for growth
- š© Youāre bored, arenāt learning or being challenged, or donāt care about what youāre working on or what your company does or who it serves
- š© Your company has an unhealthy or undesirable culture
Weāve been there.
Iām here to tell you it doesnāt have to be that way.
Why you should work at Pilot šāāļø
If you think youād 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 memoriesā¦
ā¦well then Pilot might just be the place for you.
Itās embedded into who we are. Thatās why we have a public 23-page culture code. Read it here to see if we vibe: https://bit.ly/3KmavZF
At Pilot youāll getā¦- š“ 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 youāll own your work.
- š 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.
- š Work with people who all want to be your friend (we actually hang out). Our team is incredibly talented, but we value humility.
- š¤ 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. TLāDR: this isnāt 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.
- š§Ŗ 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.
- āļø Itās travel, so itās super fun. Itās a startup, so itās super challenging with a huge upside. And itās social impact focused, so youāll actually be helping people, not just maximizing profits.
- š§³ Paid travel on occasion, for training and research. So far weāve 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 weāll keep doing them.
- š Weāre proud to have a diverse team, with plans to become a B-Corp eventually.
- ā We also have some great employer reviews here: glassdoor.ca/Reviews/Pilot-Reviews-E3311415.htm
Reviews and culture code: Glassdoor | Culture code | About Connor
āOkay, but what even is Pilot?ā š¤
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.
- š Weāve been featured by The Washington Post, WIRED, Forbes, and TechCrunch. Weāre Next Canada and Creative Destruction Lab alumni, were selected for TechCrunchās 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.
- šø Weāve 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.
- š Today weāre 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
- š 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.
- š Over 120,000 travelers have used Pilot to help book and plan their trips
- ā And it seems to be working. After 10 minutes of planning, 60% of users say theyād 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. Weāre rated 4.4 on Trustpilot. Most big OTAs sit under 2.
- š Weāre growing fast. We went from near-zero to a $1.2M gross-booking run rate in six months, on $10,500 of ad spend. Weāre live on Google Travel, which is distribution usually reserved for much later-stage companies, and weāve signed Skyscanner, Viator, GetYourGuide, Tiqets, Omio, Enterprise, and Faye.
- š§® Weāre 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 thatās us. Feel free to learn more about us at: pilotplans.com/careers
The role. The goal. š£ļø
Hereās what weāre looking for from you:
It is very simple. We want someone to own quality across the product, and the correctness of the supplier integrations we run on. We sell travel directly, so when something breaks it is someoneās real trip and our money. Nobody owns testing that surface today.
This is not a ticket-logging role. You would build the automation, own the release call, and be the reason a broken booking never reaches a customer.
What youāll be doing and learning š§āš»
You donāt 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:
Quality Ownership- Own the test strategy across web, iOS, and Android
- Build and maintain automated coverage on the flows that matter most
- Set up CI so broken things do not reach production
- Drive bugs to closure rather than just logging them
Integration Correctness- Test against the supplier and distribution systems we depend on but do not control
- Build the harnesses and mocks that let us test bookings safely
- Catch pricing, availability, and data mismatches before a customer does
- Monitor live integrations and alert when they drift
Release Confidence- Own the release checklist and the go or no-go call
- Build the dashboards that show whether things are healthy right now
- Keep regression fast enough that it does not slow releases down
Prevention- Find the patterns behind repeat bugs and push the fix upstream
- Work with support to turn real customer issues into permanent test cases
- Improve the tooling that makes everyone else less likely to break things
- Anything else as needed. We are a startup, so this is subject to change!
Treat everything above as a starting point, not a job spec carved in stone. It is not exhaustive, and it will change.
āShould I apply??!??!?ā š¤Æ
First of all, obviously.
Itās 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, youāre 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 traitsā¦
Core Technical Skills- 5+ years in QA, SDET, or integration engineering, with real automation ownership
- Strong with Playwright, Cypress, or similar, and comfortable writing the code rather than just the test plan
- Experience testing REST and GraphQL APIs, including third-party integrations you do not control
- Contract testing experience
- Mobile test automation across iOS and Android
- CI/CD pipeline experience
- Comfortable in JavaScript or TypeScript
- Experience in travel, payments, fintech, or another domain where a bug costs money is a big plus
AI & Emerging Tech- Uses AI tools to speed up development and debugging.
- Practical knowledge of LLMs, and able to build on top of existing models to sharpen product experiences.
- Accountable for the quality and reliability of AI-assisted code. Does not blindly hand off without ownership and thoughtful consideration.
How You Think- Thinks in systems and in failure modes, and enjoys breaking things on purpose
- Distrusts a green test suite that has never caught anything
- Comfortable working with logs, metrics, and messy real-world data to understand an issue
- Willing to be the person who says no to a release, and to be right about it
Mindset & Soft Skills- Able to decompose complex problems into manageable units of work.
- Knows which details to obsess over and when to move fast.
- Very strong written communication. Clear, concise, and human.
- Very curious, loves learning, and does it in their spare time.
- Low ego. Focused on solving the problem, not defending themselves.
- Loves travel and is an experienced traveler.
- Passionate about the mission and energized by the work we are doing.
Working Setup- Based in or near Bengaluru.
- Comfortable with a few hours of overlap with Pacific time a couple of days a week, and async the rest.
- Self-reliant and able to drive themselves forward without relying on management.
If you meet even 50-70% of these you could be a great fit!
Click on Apply to know more.
