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🚀 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. Read more about our unique values here: https://bit.ly/HeadoutPlaybook

👩‍💻 The role

In this role, you will work directly with our founding CXO team to solve high-priority problems that drive business growth, shape our public narrative, and help build systems that scale. You'll act as a thought partner on initiatives that span multiple markets, teams, and functions with a unique front-row seat to how strategic decisions are made and executed at a fast-growing global company.

This role places you at the heart of our operations, requiring a combination of strategic vision and hands-on execution. Your work will be crucial in ensuring that Headout's strategic objectives are met and that our growth trajectory remains on track.

🌟 What makes the role stand out?

Strategic Leadership: Partner with the founding team to develop and implement centralized initiatives that contribute to Headout's growth vision and goals.
High-impact initiatives: Collaborate with the founders on various high-impact projects across business growth, marketing, product and user experience to ensure successful outcomes.
Stakeholder Management: Maintain strong relationships with internal and external stakeholders, ensuring clear and transparent communication.
Research and Analysis: Conduct in-depth research and analysis to provide actionable insights that support strategic decision-making.

🎯 What skills you need to have

2-3 years of experience: In strategy & operations consulting, scale-up environments, or similar high-performance backgrounds.
Influential Leadership: Ability to inspire and influence teams. You excel at driving initiatives by forming partnerships and influencing simply on the merit of quality solutions.
Project Management Expertise: Strong track record in leading complex projects from inception to completion. You possess exceptional organizational skills and can manage multiple priorities effectively.
Strategic Thinker: Capable of high-level strategic thinking and detailed execution. You can grasp the organization's vision and translate it into actionable plans.
Analytical Skills: Excellent research and analytical capabilities. You can synthesize information to provide actionable insights that support strategic decision-making.
Communication Skills: Exceptional verbal and written communication skills. You can convey complex information clearly and effectively to diverse audiences.

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 life@headout.com.

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.

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Founders' Office - Strategy