Senior AI/ML Engineer

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, where you want, with who you want. 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 our AI strategy and roadmap, and then go and build it. Because both the trip and the booking live with us, we hold context most travel companies never see: who is going, what they care about, what we suggested, and what they actually did about it. Turning that into a system that reads intent and matches it is the core of what we are building.

This is not a role where you get handed a spec. You would shape what we build and in what order, then build it.

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:

Owning the AI Strategy

• Define what we build, in what order, and why
• Decide where a model earns its place and where something simpler wins
• Keep us complementary to the frontier models rather than competing with them
• Bring the rest of the team along, in plain language

Reading Intent

• Build the per-trip layer: the context of the trip in front of us, who is going, and what they are still deciding
• Build the ambient layer: the preferences and taste that hold across someone’s trips, without making them spell it out every time
• Work on group intent matching, so we can tell what a set of people with different preferences will actually agree on
• Turn all of that into personalisation and recommendations people trust

Building the Systems

• Build and own the data pipelines that structure messy trip data
• Design the feedback loops that make every trip improve the next result
• Integrate LLMs where they help, and manage the cost, latency, and quality tradeoffs
• Build retrieval and generation systems, including content produced at scale that both people and AI tools can find

Proving It Works

• Own evaluation and experimentation so we know something is better before we ship it
• Treat conversion as the measure of success, not model metrics
• Handle cold start and sparse data honestly rather than pretending it away
• Evaluate rigorously. We do not ship on vibes
• 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 Technical Skills

• 5+ years in ML engineering, with recommendation, ranking, search, or personalization systems in production
• Strong Python, and comfortable enough in TypeScript or Node.js to ship into our stack
• Experience building retrieval systems, embeddings, and vector search
• Practical LLM experience: prompting, fine-tuning, evaluation, and cost control
• Experience with offline evaluation and online A/B testing, and knowing when each one lies to you
• Experience with data pipelines and feature stores
• Google Cloud Platform experience is a plus
• Published research is a plus but shipped systems matter more

Judgment

• Knows when a heuristic beats a model, and says so out loud
• Optimizes the metric that matters to the business, not the one that is easy to move
• Comfortable with sparse, messy, real-world data
• Understands cold start, and how to ship something useful before the data is good
• Accountable for the quality and reliability of AI systems. Does not blindly hand off without ownership and thoughtful consideration

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!

“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!! 🙋‍♂️