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. 

• Own key attraction partnerships. Manage and grow relationships with some of Headout's most important global partners, developing long-term commercial strategies that unlock sustainable growth for both Headout and our suppliers. 


• Drive growth. Identify new commercial opportunities, expand existing partnerships, onboard new supply partners, and expand the breadth and quality of our inventory across Italy. 


• Collaborate. Work closely with cross-functional teams including Operations, Product, Tech, Marketing, and Customer Experience to ensure seamless execution, exceptional partner satisfaction, and continued growth in sales and bookings.


• Optimize. Analyze market trends, partner performance, and customer demand to develop strategies that maximize revenue, improve distribution, and strengthen long-term partnerships.

What skills & experience do you need?

• Native Italian and fluent English speaker, based in Rome. 


• 2-5 years in business development, sales, or key account management.


• Proven ability to manage senior external partners while collaborating effectively with cross-functional internal teams.


• Strong operational skills with a hands-on approach.


• Analytical, with excellent communication skills and a global mindset.


• Team player who thrives in diverse, multicultural environments.


• Experience with CRM systems and a willingness to learn new tools.

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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.