🚀 Why Headout?

We’re a rocketship: 9-figure revenue, record growth, and profitable

With $200M+ in revenue, guests in 700+ cities, and 18 months of profitability, Headout is the fastest-growing marketplace in the travel industry, and we’re just getting started. We've raised $60M+ from top-tier investors and are building a durable company for the long term — because that's what our mission needs and deserves. We’re growing, profitable and nowhere near done.

What we do is important

In an increasingly digital world, there is a desperate need to augment our human experience by getting us to interact with the real world around us and the people in it. At Headout, our mission is to be the easiest, fastest, and most delightful way to head out to a real-life experience — from immersive tours to museums to live events and everything in between.

Why now?

The foundation is strong. The opportunity ahead is even bigger. We’ve hit profitability, built momentum, and proven the model — but there’s so much more to build. If you’re looking to join a company where the trajectory is steep and your impact is real, this is the moment.

Our culture

Reinventing the travel industry isn't easy, but that's the fun part.

We care deeply about ownership, craft, and impact, and we’re here to do the best work of our careers. We won’t pretend like it’s for everyone but if you’re a builder who loves solving tough problems, you’ll feel right at home.

👨‍💻 The Role

As a Staff Engineer at Headout, you will drive architectural excellence and technical strategy across multiple product engineering pods. You'll solve some of our most complex, high-impact engineering challenges: designing very low-latency systems that power dynamic pricing strategies, processing large-scale inventory data across tens of thousands of products, and managing vendor ecosystem coordination spanning almost half a million vendors growing everyday. Beyond building systems, you'll be a force multiplier for technical excellence, partnering with Engineering Managers to eliminate technical debt, improve deployment stability, and build resilient system boundaries that allow our teams and business to scale sustainably. Your work will shape how we architect systems for the next phase of growth.

🤩 What Makes This Role Special?

Large-Scale System Design: Design very low-latency systems solving critical business challenges: dynamic pricing strategies, large-scale inventory data processing across tens of thousands of products, and vendor ecosystem management spanning almost half a million vendors. See your architecture impact millions of travelers in real-time.
Strategic Technical Debt Reduction: Lead systematic reduction of technical debt across pods, reshaping system architecture to improve deployment stability, reduce operational complexity, and enable teams to scale with confidence. This is career-defining work that prevents future chaos.
Architectural Ownership Across Boundaries: Own architectural decisions that span multiple pods and teams. Guide the design of resilient, high-availability systems without needing direct authority—influence through technical excellence and clear thinking.
Technical Excellence Meets Business Impact: Partner closely with Engineering Managers to balance technical excellence with delivery velocity. Influence critical decisions on architecture trade-offs, ensuring we build for both today's needs and tomorrow's scale.
Design Leadership & Mentorship: Elevate engineering standards across your pod ecosystem through design reviews, code reviews, and mentorship. Shape how systems are built and help other engineers grow as technical thinkers.
Profitable, Sustainable Growth: Work on systems directly powering millions of travelers worldwide in a profitable, bootstrapped company. Your architectural decisions have immediate business impact—no endless VC burn, real product-market fit.
Modern Distributed Systems Stack: Build with cutting-edge technologies solving real distributed systems challenges: Kafka for event-driven architectures, Kotlin and Spring Boot for backend excellence, PostgreSQL and MongoDB for complex data models, and AWS for cloud-native infrastructure.