🚀 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?
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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.
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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.
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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.
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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.
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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
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