About this role
🚀 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 We’re looking for a Senior Product Manager (User Experience) to join the Product team at Headout and lead how users experience our products end-to-end — across discovery, decision-making, booking, and post-booking journeys.
In this role, you’ll be accountable for experience quality, coherence, and usability across complex user journeys. You’ll partner deeply with Design, Engineering, Data, and Research to identify friction, shape intuitive experiences, and ensure that what we build is not only functional, but genuinely easy and delightful to use.
As Headout scales from 5k experiences in 190+ cities to 50k experiences in 500 cities, experience consistency and clarity become critical differentiators. This role sits at the intersection of user empathy, product strategy, and execution, shaping how millions of users interact with Headout globally.
🤩What makes this role special?
Own Experience, Not Just Features: You’re responsible for how the product feels and works for users — not just what ships. Work on Real, Messy Journeys: Tackle complex, multi-step user flows with real trade-offs, constraints, and scale challenges. Design Is a Core Partner: You’ll co-own problems with Product Designers, shaping experience principles, interaction patterns, and UX strategy. Impact at Scale: Small improvements compound across millions of sessions, bookings, and repeat users.
🌟What You’ll Work On
Own the user experience vision and roadmap across key customer journeys on Headout. Identify experience gaps through research, usability testing, analytics, and direct user feedback. Break down complex journeys into clear problems, experience principles, and prioritised opportunities. Partner closely with Design to define flows, information architecture, interaction models, and usability standards. Collaborate with Engineering to balance experience quality with technical constraints and delivery timelines. Drive alignment across teams to ensure experiences are consistent, intuitive, and scalable. Advocate for the user in prioritisation discussions, roadmap decisions, and trade-off calls. Measure experience quality using a mix of qualitative insights and quantitative metrics (conversion, drop-offs, task success, repeat usage). Raise the bar on user-centered thinking across the product organisation.
đź’ťWhat skills & experience do you need?
4+ years of experience in product management, with strong ownership of consumer-facing, UX-heavy products at scale. Demonstrated track record of leading and improving end-to-end user journeys (not just shipping isolated features). Deep comfort working with Product Designers on discovery, interaction design, usability testing, and experience quality. Strong intuition for user behaviour, paired with data-informed decision making. Ability to translate ambiguous user problems into clear experience principles, product direction, and execution plans. Excellent communication skills, especially in articulating user problems, experience trade-offs, and design rationale. High ownership mindset with comfort leading cross-functional teams through ambiguity and complexity. Experience operating in fast-paced, collaborative product teams with evolving priorities.
🥰 What Will Help You Succeed
Strong user empathy paired with a bias for action. Comfort operating in ambiguity and making informed trade-offs. Ability to build trust through clarity, consistency, and follow-through. Curiosity to learn, test, and continuously raise the bar for outcomes.
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.