Lead Software Engineer, Web

Why Headout?

We’re a rocketship: 9-figure revenue, record growth, and profitable. With $130M in revenue, guests in 100+ 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 Frontend Lead at Headout, you’ll own the quality, architecture, and delivery of our web interfaces. You’ll combine strong frontend engineering skills with thoughtful leadership to build scalable, high-performance web experiences used by a global audience. Beyond writing code, you’ll guide frontend direction across projects, set technical standards, and work closely with product, design, and backend teams to ensure what we build is robust, maintainable, and user-friendly.

What Makes This Role Special

• Own Frontend Architecture: Design and evolve scalable frontend systems that support long-term product growth.
• Lead by Example: Drive projects end-to-end while setting high standards for code quality, performance, and UX.
• Collaborate Deeply: Partner with product managers, designers, and backend engineers to translate ideas into reliable interfaces.
• Grow the Team: Support and guide frontend engineers through feedback, reviews, and shared best practices.
• Make Smart Tech Choices: Evaluate new tools and frameworks thoughtfully, balancing innovation with stability.

What Skills & Experience You Need

• 6-8 years of experience in frontend development, building and shipping production web applications.
• Strong expertise in JavaScript (ES5/ES6), TypeScript, HTML, CSS, and modern frontend architecture.
• Experience designing scalable, performance-optimized frontend systems.
• Comfort working with Node.js, browser dev tools, and both CSS-in-JS and traditional CSS approaches.
• Solid understanding of web performance, responsiveness, and browser compatibility.