🚀 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

🤩 What makes this role special?

• Own the Strategic Narrative: You will own the end-to-end analytical roadmap for our Growth and Marketing teams. You'll translate complex datasets into clear, compelling narratives and present your findings to senior leadership, directly influencing our P&L and strategic direction.
• Partner with Leadership: Act as a dedicated strategic partner to our leadership across Marketing, Business, and Operations. You'll be the go-to expert, providing the critical insights that shape their decisions on budget allocation, channel optimisation, and international growth.
• Build and Mentor a World-Class Team: You will hire, manage, and develop a team of talented data analysts. You'll foster a culture of excellence, curiosity, and impact, leveling up the team's skills in analytics, storytelling, and commercial thinking.
• Drive Business Impact: Go beyond insights to drive tangible outcomes. You will design and analyse A/B tests, build sophisticated attribution models, and create frameworks to measure the ROI of every growth initiative, ensuring our efforts are both impactful and efficient.

💝 What skills & experience do you need?

• A Leader and Influencer: You have demonstrable experience managing and mentoring analysts, coupled with a proven ability to partner with and influence senior business stakeholders (Director, VP level).
• Strong Commercial Acumen: You think like a business owner. You instinctively connect data points to financial outcomes ($) and can articulate the "so what?" behind every analysis.
• Deep Domain Expertise: You have hands-on experience untangling the complexities of digital marketing and business analytics. You're comfortable dissecting performance marketing channels (Paid Search, SEO, Affiliates, CRM) and modeling business drivers like LTV and CAC.
• Technical Proficiency: Your technical toolkit is sharp. You possess advanced proficiency in SQL for complex analysis and are comfortable with a scripting language like Python or R for statistical modeling. Experience with modern BI tools (e.g., Looker, Tableau) and data warehousing concepts is essential.
• A Pragmatic and Strategic Mindset: You are an analytical, creative thinker who can navigate ambiguity. You have a bias for action and know how to make the right trade-offs between speed, depth, and accuracy to deliver maximum impact.
• Passion for the Mission: You are genuinely excited by the challenge of using data to help people discover and experience the world.

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.