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Love Your Work
If a decision isn't a HECK YES, it's a NO. We're passionate about what we build, and we have fun doing it.
Careers at Pilot
Radical autonomy, at Work.
The same autonomy we give travelers is the autonomy we give our team, freedom to build tools that help people explore the world together, their way.
Rated one of Forbes "Best Startup Employers".
See Open Roles
Rated 4.9 on Glassdoor
Scroll to explore the life
Why Pilot
Enabling people everywhere to discover and share memorable moments in the real world
Starting with travel, through our collaborative platform for booking and planning trips.
70K+Trips already planned on Pilot
Our Values
The compass we travel by.
These guide the products we build, how we work together, and our ethos of radical autonomy. At the core, it's about treating people like adults.
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People First
We lead with humility. We don't think less of ourselves, we just think of ourselves less.
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Take it Further
We challenge the status quo, stay endlessly curious, and go a step beyond what's expected.
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Move Fast with Data
We decide with data and experimentation, not endless analysis. We ship, learn, and iterate.
Become the best version of yourself.
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Help people
Take the stress out of travel so people can spend more time making memories with the people they love.
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Have an impact
Small team, big ownership. Your work ships and shapes the product real travelers use every day.
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Actually like your job
Enjoy your work and the company you keep. We build a place people are genuinely excited to show up to.
The Perks
A life well travelled, on and off the clock.
Everything we offer maps back to our values. Here's what that looks like in practice.
How we put people first
Autonomy & Freedom
- Competitive salary, equity & benefits
- Real control over your life and your work
- Own your decisions
- Set your own goals and projects
- Zero bureaucracy or micromanagement
- Leads can't just delegate work they don't like, they have to share the load
- Unlimited paid vacation with approval, normalized by year end so everyone gets the same amount
- Work when and where you want
- 4-day work week when work is finished early
- Paid travel & team trips
- Humble leaders and a flat hierarchy
- Accountability & strategic consistency
- Structure & support when you need it
- No meetings that could have been an email (we actively minimize this)
Why we love our work
Community & Impact
- No ceiling on the type of work you can take on
- You'll feel genuinely cared for
- Strong relationships across the team
- We actually hang out, but don't force you to
- Impact over profit, we always ask "would the customer love this?"
- Team and leaders who have your back
- A collaborative, supportive culture
- A real focus on mental health
- Never hear the word "synergy" or made up corporate jargon again
Taking it further
Learning & Development
- It's okay to fail, that's how we learn
- Set your own learning goals
- Challenging, meaningful projects
- Work alongside genuinely smart people
- Hackathon-style teams
- Lead your own projects
- Direct feedback, delivered with kindness
- Everyone ships code and talks to users (you'll learn if you don't know)
Move fast with data
Respect & Recognition
- Transparency across the company, from financials, metrics, and more
- Cross-functional collaboration
- You're encouraged to speak up and share opinions
- Work that genuinely matters
- Everyone is treated fairly
- You don't have to ask for a raise or promotion to get one
- You don't have to wait for someone to leave to move up, impact (which you control) is rewarded, not seniority
Work stuff, but make it fun
Applying is easy.
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Fill out the application form
It lets you skip the screening call and get fair, thoughtful consideration.
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Interview with the hiring leads
A short, role-specific conversation with the team leads you'd actually be working alongside.
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Meet the CEO
A quick chat with Connor, plus a reference check. Then we make it official.
Mindset
Get to know how we really think.
We wrote it all down. Dig into what we care about, how we make decisions, and what it's actually like to build here.
Meet the team
Our crew, your mates.
A small, mighty, and slightly goofy team who ship code, talk to travelers, and genuinely like each other.
Core Memory Capturer
Tayah Lee
Product Design
Stoic Programmer
Sadab Wasim
Mobile Development
Techie Trekker
Naman Gupta
Full Stack Development
Driven by Gratitude
Yaidzu Nakashima
Support & Operations
Not a Twin, But Almost
Ayush Maurya
Full Stack Development
Always Curious
Jennifer Huang
Support & Operations
Flower Lover
Samantha Glassner
Group Travel Planning
Perpetual Dreamer
Avinash V K
Co-Founder, Engineering
Competitive Gamer
Yu-Wei Hung
Co-Founder, Product
Team first! Also dad jokes.
Connor Wilson
Founder, CEO
The last word
We love working here. You will too.
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.
- Great employee reviews
- A diverse, kind team
- Dad jokes from our CEO
Hiring plan
Find your seat on the trip
Now sourcing candidates for roles we're looking to fill by late 2026. Tap one to tell us you're interested and apply for consideration. You can also follow us on LinkedIn or Wellfound below for job alerts when more roles are posted.
Stay updated when new roles open.
No form to fill out, just follow us and let the job alerts come to you. We post every new role to LinkedIn and Wellfound.