We're Outfit Labs - building a product that helps people feel truly known wherever they go. We believe people deserve to discover places that genuinely fit who they are, and more importantly, understand why those places are perfect for them.

We believe:

That humans are unique and deserve to be heard and listened to
That where folks choose to go ought to be a reflection of who they are as a person
That AI should make our experiences more human and personal, not less

Instead of showing you generic 4-star hotels, we surface places that match your personality, your preferences, your vibe - and we tell you exactly why each place fits you. Our team includes over a dozen travel tech veterans. We're currently in closed beta with a waitlist and first revenue coming in.

The Role

You'll own customer experiences end-to-end - from understanding user needs to shipping features that solve real problems. As a Product Engineer, you'll think like a product person and build like an engineer, bridging the gap between what users want and what's technically possible.

You won't be alone: every feature includes a human copilot from the opposite domain who helps you think through solutions and validate product decisions.

Our philosophy: If it doesn't impact the customer experience, we shouldn't be doing it.

The team you're joining: 7 engineers in Chicago with our CTO and 2 technical leads onsite. We love mentoring engineers who are excited to learn both product thinking and technical execution.

About You

You're the kind of person who builds things for fun and thinks about users while you do it. You've probably got GitHub repos with weekend experiments, you've built a web app to solve a problem you actually had, or you've spent time thinking about why certain products work better than others.

We're looking for engineers who think "I wonder if I could build that better" when they see products that miss the mark, not just "I wonder how that works."

What We Need

Programming experience: Solid with at least one modern language, exposure to others
Fullstack builds: You've made applications with both frontend and backend components
AI curiosity: You've experimented with LLMs, APIs, or prompt engineering
Learning agility: You pick up new technologies without starting from scratch

Collaborative approach: You ask questions, learn from others, and enjoy working as part of a team

Our Stack and Tools

Backend: Kotlin, Spring Boot, Langchain, PostgreSQL, Redis, AWS
Frontend: NextJS, TypeScript, Tailwind CSS, some Vite experiments
AI: Access to SOTA frontier models
Development: We're open-minded to test everything. Today we make heavy use of AI coding assistants

Our Values

Listen First:We are curious, empathetic, and authentic. We listen to our teammates and show up prepared to be listened to. We talk to our customers and prove hypotheses using data. We are inclusive and open-minded. We leave our egos at the door and win as a team
Build with Optimism: We take big swings and bias toward action. We prioritize the hardest puzzles knowing great things require persistence. We invent products, concepts, and ways of working, celebrating both the successes and the learnings.
Leave it Better:We want a better world for our kids. We don't stay in our lanes - we take out our trash, comment on each other's code, engage in healthy debate, and build things we can be proud of. We use AI responsibly.

Why Join Outfit Labs?

Help people be truly known: Build an AI product that understands what makes each traveler unique and surfaces places that genuinely fit them
Solve a deeply human problem: Create technology that makes people feel seen and understood wherever they go
Learn from experienced builders: Work alongside founders who have been on the zero to one journey with several successful exits to their name
AI-native development: Learn prompt engineering as a core skill alongside traditional development
Own real impact: The features you build will help thousands of people discover places they'll love and understand why
Growth trajectory: Go from junior engineer to full-stack + AI expert faster than anywhere else
Equity opportunity: Meaningful participation in a growing travel tech company
Chicago tech scene: West Loop office, walking distance to the best restaurants in the city and less than a block from Ogilvie Transportation Center.

Benefits:

Health, dental, vision insurance, unlimited PTO, hybrid work schedule (Mon/Fri remote), latest equipment

Salary Range:$75-95k/annually (+ opportunity for options in an early stage startup)

We're looking for evidence of both technical curiosity and product empathy.Someone who builds things and thinks about users beats perfect technical portfolios every time.

Ready to Build the Future of Travel?

If you're the kind of person who builds side projects on weekends, gets excited about AI possibilities, and wants to help travelers find places that actually fit who they are, we want to talk.

We value applications from everyone. Diverse perspectives make our products better.

Even if you don't check every box above, apply anyway. We'd rather hire someone who's genuinely curious and motivated than someone who looks perfect on paper.

Requirements: Must be authorized to work in the US and able to work from our Chicago office Tuesday-Thursday. No relocation assistance or visa sponsorship.

Outfit Labs is an equal opportunity employer committed to creating an inclusive environment for all employees.

Outfit Labs remote jobs

Fullstack Engineer - Travel Tech Startup