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Why Headout?

We’re a rocketship: 9-figure revenue, record growth, and profitable

With $200M+ in revenue, guests in 700+ 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 hiring a Senior Content Writer to own content quality and completeness across a portfolio within an assigned market, with a clear path toward deeper ownership of that market’s organic growth story.

This role runs on Headout’s automated content workflows. Most of your day-to-day will involve high-judgment editing of AI-generated content rather than writing from scratch. The job is not to mechanically QC drafts or rewrite everything manually. It is to apply strong editorial judgment: identify weak research, missing customer information, structural gaps, unclear claims, and content that may technically be correct but still isn’t useful enough.

As you become fluent in the system and your market, the role expands from content execution into performance analysis, opportunity identification, and portfolio-level thinking.

🤩What makes this role special?

High-Impact Role.

You’ll own the quality and completeness of the content portfolio assigned to you within Headout’s MMP production system, while building toward broader ownership of content performance within your assigned market.

Hands-On Editorial Judgment.

Most of your day-to-day will involve editing AI-generated product content, landing pages, and supporting pages for clarity, accuracy, structure, usefulness, and brand voice. You’ll independently verify nuanced or ambiguous claims and strengthen shallow or incomplete AI-generated research.

Performance & Growth Ownership.

As you build fluency, typically from around month 2, you’ll start using traffic, rankings, CTR, conversion, and other available signals to understand where your portfolio is and isn’t performing. You’ll diagnose why a page or content cluster may be underperforming and identify content gaps and missed organic opportunities.

Play With Technology.

The role runs on automated content workflows and structured tooling. You’ll develop strong fluency with the systems you work in and flag recurring friction, gaps, and opportunities to improve the workflow for the wider team.

Build Better Systems.

The role has demanding turnaround expectations, but the workflows are designed to make that pace sustainable. We expect you to surface anything that repeatedly creates unnecessary work, weakens output, or slows execution, and help make the system better over time.

💝What skills & experience do you need?

• You have

3–5 years of experience

writing or editing digital content, with strong independent editorial judgment.

You Have Strong Editorial Judgment.

You can distinguish between content that is merely factually correct and content that is genuinely useful, complete, and decision-oriented.

You’re A Strong Researcher.

You have strong research instincts and are comfortable independently validating complex or ambiguous information.

You’re Comfortable With Systems.

You’re comfortable working within structured tooling and workflows rather than defaulting to manual processes.

You Understand Content Performance.

You have working fluency in SEO and basic content performance metrics such as traffic, rankings, CTR, and conversion.

You’re Analytical.

You can investigate why something may be underperforming and form a reasoned hypothesis from available data and content context.

You’re An Owner.

You take strong ownership and communicate early when scope, dependencies, or workflow issues could affect quality or turnaround.

You’re Comfortable With A Learning Curve.

You’re motivated by becoming faster and more effective through better systems.

➕Bonus

• You have experience mentoring or reviewing the work of junior writers.
• You have prior ownership of a market, vertical, content portfolio, or production pipeline.
• You have experience working with content performance data or content-led growth.
• You have a background in travel, live entertainment, marketplaces, or e-commerce content.
• You have experience reviewing, improving, or working with AI-generated content.

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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 you apply for this job profile your personal data will be retained for a period of (1) year. Headout shall process this data for recruitment purposes. the relevant job profile is filled or the time period of (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.

• You have experience mentoring or reviewing the work of junior writers.
• You have prior ownership of a market, vertical, content portfolio, or production pipeline.
• You have experience working with content performance data or content-led growth.
• You have a background in travel, live entertainment, marketplaces, or e-commerce content.
• You have experience reviewing, improving, or working with AI-generated content.