Staff Engineer, Web

With $200M in revenue guests in 700 cities and 18 months of profitability Headout is the fastest-growing marketplace in the travel industry and were just getting started. Weve raised $60M from top-tier investors and are building a durable company for the long term because thats what our mission needs and deserves. Were growing profitable and nowhere near done.

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.

The foundation is strong. The opportunity ahead is even bigger. Weve hit profitability built momentum and proven the model but theres so much more to build. If youre looking to join a company where the trajectory is steep and your impact is real this is the moment.

Reinventing the travel industry isnt easy but thats the fun part.
We care deeply about ownership craft and impact and were here to do the best work of our careers. We wont pretend like its for everyone but if youre a builder who loves solving tough problems youll feel right at home.

Hi Im Aakash Director of Engineering at Headout. Im looking for a Staff Engineer Web to shape how Headouts consumer teams design build and learn in an AI-native world. You will stay close to hard web engineering problems while setting patterns that other teams can use not simply advise from the sidelines.

The interesting challenge is not getting an agent to produce a page. It is making sure the page respects the design language behaves well in production and teaches us something when it changes. I want someone who can make that work verifiable and who can turn good local solutions into useful shared tools without imposing a platform for its own sake.

Headouts consumer teams work like a lab: experiments tell us what is worth building further and what should be shelved. AI has made it faster to build but that speed has not yet translated into equally fast trustworthy experimentation. The opportunity is to make design development verification and measurement work together so humans and agents can safely propose run and learn from product changes.

• Design-system adherence for agent-built work. Define the contracts and engineering checks that help agents build within an established design language whether extending an existing experience or launching something new. Make exceptions deliberate visible and manageable.
• Verification that earns trust. Build evaluation and review loops that catch real defects and protect design fidelity. Connect checks before release with what actually happens in production rather than rewarding teams for passing a suite that misses the user experience.
• Experimentation as a usable platform. Shape the infrastructure that lets people and agents propose experiments run them with controlled audiences measure results and learn. Treat measurement safety and the ability to stop a bad change as part of the design.
• Shared architecture across consumer pods. Spot where repeated solutions should become a common abstraction and where teams need room to differ. Help teams adopt the right shared patterns through clear contracts and practical migration paths.
• Hands-on technical leadership. Get into complex web problems with teams test solution paths in code and help engineers make stronger decisions. The work spans deep engineering judgment and a longer-term view of how design and development should collaborate with agents.

• You have at least 9 years of engineering experience with substantial hands-on depth in consumer web engineering including React and TypeScript and can reason about rendering performance resilience and production trade-offs.
• You have led technical work across teams without relying on reporting lines. You know when a shared abstraction helps and you can earn adoption rather than mandate it.
• You have built or governed design systems quality gates experimentation or measurement infrastructure and can explain how you knew they worked.
• You are curious about AI-assisted engineering but insist on evidence guardrails and clear failure modes. You can work through ambiguity while keeping your standards high.

• You prefer a purely advisory architecture role and do not want to join difficult work in the code.
• You are satisfied with prompt instructions alone when an agents output needs enforceable checks.
• You want to build a shared platform without investing in adoption measurement and migration.

We want you to see the real problems and have room to ask questions throughout.

• Recruiter conversation. We discuss your web depth cross-team work and interest in the charter.
• Technical deep dive. We explore design-system guardrails experimentation and the choices involved in building a platform for several teams.
• Live build. Show how you work with AI to solve a web and design-system problem showing how you direct and verify its work. Setup details will be provided in advance.
• Web system design. We work through a consumer experience including performance reliability experimentation and release.
• Leadership conversation. We discuss technical vision influence across teams and how you raise standards.

At Headout we dont 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. Headoutprovidesequal employmentopportunities (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 .

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 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.