Headout

Some experiences you just can’t scroll past, and Pompeii by Night is one of them. 👀 For just 10 nights this September & October, the ancient city opens after dark. Wander its ruins under the stars, guided in English or Italian, and see Pompeii in a way most travelers never will. 👇 Nights like these don't wait around, and neither should you! More in the comments.

Running offers on Headout shouldn't feel like extra work. With our upgraded Ventrata integration, it doesn't. Partners can now set up Headout-exclusive discounts in just a few clicks. No duplication, no messy reconciliations, no hassle. And the result? More visibility. Better conversion. Happier guests. We’re making it easier than ever to stand out on Headout. It's your turn now. 💜

27 championships. Countless legends. And now, one more win: a brand-new partnership. We’re teaming up with the New York Yankees to bring their magic closer to fans everywhere. Whether you bleed pinstripes or it’s your first game in the Bronx, there’s nothing like the roar of Yankee Stadium. And now, you can book it all, faster and easier, with Headout. 💜 👇 More details in the comments.

What’s a trip to London without a night at the theatre? 👀 We’ve partnered with Delfont Mackintosh Theatres Ltd. — whose theatres host some of the West End’s most iconic productions — to make your next night out easier, faster, and just a few taps away. Together, we’re making it simpler than ever for tourists to experience London’s theatre magic the way it was meant to be: iconic, unforgettable, and now, effortlessly bookable.  Get your front-row seats to the world’s greatest stages now! 💜

Some Headouters make their mark from day one. Others quietly shape everything around them—building, lifting, and leading, year after year. Today, we’re celebrating four such incredible folks who’ve done exactly that. Rachit: The engine behind our engineering. Calm, clear, and quietly intense, Rachit has a knack for rallying teams and turning ideas into reality. Whether laying foundations or breaking new ground, he leads with craft and conviction. Atish: Few grow the way Atish does. He’s tackled some of our hardest, most ambiguous challenges with focus, grit, and humility, and made it all look easy. Thoughtful, dependable, and never one to chase the spotlight. Meghana: From running Supply Ops to building systems from scratch, Meghana’s done it all, with heart. Strategic, steady, and always five steps ahead, she’s a master of the Headout playbook (even while holidaying in Europe 😉 ). Shubham: Steady, sharp, and deeply dependable, Shubham is the teammate everyone leans on. Whether it’s high-stakes calls or high-pressure moments, he shows up with clarity and care, always leading with ownership, and never looking for credit. To Rachit, Atish, Meghana, and Shubham: thank you for being the kind of teammates who make Headout everything it is. We can't wait for what's next. 💜

Inspiration strikes everywhere and nowhere at Headout. Take this fire extinguisher, for example. Most people would see safety equipment. We saw a design brief. So we did what any mildly unhinged, highly caffeinated team would do: gave it a wall, hit the spotlight, and crafted a dramatic arc. Is it functional? Absolutely. Fabulous? Obviously. Does it now make people stop, stare, and question our sanity? 100%. That's what our office is like: travel dreams get built, and bizarre ideas aren’t just welcome, they’re wall-worthy. So if your imagination tends to wander into mildly absurd, wonderfully clever places, we should talk. We're hiring across the board. Come make weird (and wildly impactful) things with us. 💜 Link in the comments.

Travelers love feeling like they've beaten the system. So we built a feature that lets them do just that. Meet Drops, our way of making discovery addictive, delightfully unpredictable, and just a little competitive. Think AED 49 for a Dubai yacht cruise. Or skip-the-line tickets that disappear in seconds. Catch one if you can. And even if you're late to the party, there’s always a little win waiting—just enough to keep you coming back. With Drops now live in Paris and Rome, there’s even more to stumble upon. 😉 Go behind the build to see why Drops is quickly becoming our most-loved experiment. More in the comments. 👇

Travel shows you a new side of the world, and sometimes, a side of your travel partner you did not sign up for. We asked the team what makes or breaks a travel buddy, and let's just say the answers were brutally honest. And hilarious. 😂 👀 What's your biggest red flag in a travel partner?

8 years ago, two very different Headouters joined us — and have left their mark on everything since. Karthik: From operations to performance marketing, he’s seen (and done) it all. A quiet powerhouse who brings clarity in chaos, asks questions that matter, and lands the best one-liners. If it’s in his hands, you know it’ll be well thought through, well executed, and somehow, still fun. Ravi: The human Swiss Army knife. He’s juggled roles, solved the unsolvable, and now builds product like he’s been doing it forever. And through all of this, he's always solving, always shipping, and somehow, always smiling. His grasp of how things work (and how to make them better) is second to none. Karthik and Ravi, thank you for being the kind of teammates every team hopes for. Here’s to year 9, many more FIFA matches, and showing up like it's day one. 💜

We just wrapped our second ESOP buyback at Headout — fully funded from our balance sheet, with 250+ teammates across 11 global offices participating. This marks our second buyback since 2022, and it’s a continuation of what we’ve believed from day one: if you help build something, you should share in the value it creates. Ownership here isn’t a buzzword. It’s a real stake. Shared, earned, and celebrated. 💜 Every teammate gets ESOPs on day one and at key milestones throughout their journey. Through COVID, through scaling, and through everything in between, that principle hasn’t changed. We’re just getting started. And we’re building a company where the upside belongs to all of us. 🤝