Lead Product Designer

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

Design at Headout is core to how we build products by shaping strategy, defining direction, and staying involved from early exploration through implementation and iteration.

We are building for a truly global audience, with users from almost every country using our product in 14+ languages. Designing at this scale means building systems that work across geographies, languages, and use cases, while still feeling simple to someone booking in a hurry.

As a Lead Product Designer, you will shape how users discover, decide, and book experiences, and how that journey holds up when things get real. From the moment they first encounter Headout to post-booking, you will craft experiences that help users make confident decisions and keep coming back.

What makes this role special?

• From India, to the world: Design for a truly global audience, with users from almost every country using Headout. One day you might be helping a couple in Tokyo plan their day, the next a family from Australia figuring out a last-minute booking, or a solo traveler in Europe trying to make a quick decision on the go.
• Shape how design works: We’re a small, high-agency team where designers own problem spaces end to end and actively shape how we build, especially as we move toward an AI-first way of working.
• Build experiences that users can trust: We care deeply about making complex decisions feel simple and reliable. Good enough doesn’t cut it here, especially in the moments users rely on the most.
• Iterate fast, learn faster: You’ll work on real problems with tight feedback loops, where every decision is an opportunity to improve the experience and learn.

What skills & experience do you need?

• 5-8 years of experience designing consumer-facing digital products across mobile and web, working closely with cross-functional product teams.
• Ownership of both user experience and product metrics, with a track record of driving meaningful improvements for users and the business.
• Ability to define the right problems, not just solve them, by turning ambiguous inputs and fragmented insights into clear product opportunities.
• You use AI across your workflow to explore multiple solution directions, uncover edge cases, and improve both speed and quality, while moving beyond static design by prototyping ideas and working closely with engineers to ship them. 
• Experience contributing to production using AI tools like Cursor, Claude Code, or similar. If you haven’t done this before, you’ll have the chance to learn it by building at Headout.
• A high bar for craft, with strong attention to detail across UI and interactions that build trust in the product.
• Strong collaboration skills, with the ability to influence product direction and align teams around the right problems and tradeoffs.
• You  raise the bar for design across the team by influencing product thinking, improving craft, and helping other designers make stronger decisions.

EEO statement

At Headout, we don’t just accept differences - we celebrate it, we support it, and we thrive on it for the benefit of our employees, our partners, and the community at large. Headout provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. During the interview process, if you need assistance or an accommodation due to a disability, you may contact the recruiter assigned to your application or email us at [email protected].

Privacy policy

Please note that once you apply for this job profile your personal data will be retained for a period of one (1) year. Headout shall process this data for recruitment purposes only. Once the relevant job profile is filled or once the time period of one (1) year from the date of the job application has passed, whichever is later, Headout shall either delete your data or inform you that it shall keep it in its database for future roles. In compliance with the relevant privacy laws, you have the right to request access to your personal data, to request that your personal data be rectified or erased, and to request that the processing of your personal data be restricted. If you have any concerns or questions about the way Headout handle your data, you can contact our Data Protection Officer for more information.