Headout

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. 🤝

10 years ago, Viraaj walked in as one of our first-ever teammates. Back then, we had big dreams, no playbooks, and one dashboard that worked (sometimes). He joined our Customer Experience team. One minute he was answering guest questions, the next he was fixing bugs. No job was too small, no idea too bold. Since then, he’s helped build the foundation we stand on today. Teams, rituals, values. So much of what makes Headout feel like Headout has Viraaj’s fingerprints all over it. Now he leads everything to do with Culture and Talent. But that title barely scratches the surface. Viraaj is who you turn to when things get messy. He’s the one who reminds us what really matters, even when it’s tough. He’s the reason “people-first” isn’t just something we put on our website. It’s how we work, every single day. That’s why we made June 30 Headouter Day. Our one custom, Headout-only all-company leave across offices. A pause to celebrate the people we’re building with. A sign that Headout is, and always will be, about its people. Here’s to you, Viraaj. 10 years. Countless memories. And a legacy that keeps growing. We couldn't have written our story without you. 💜

London is calling…and so is the West End. This summer, we’re helping tourists experience the very best of London’s theater scene; with exclusive prices on the West End’s most iconic productions. Some of the stars of the lineup: ✨ Wicked 🪄 Harry Potter and the Cursed Child 🎩 Cabaret 🕺 The Great Gatsby 🐻 My Neighbour Totoro We’re making world-class theater easier, faster, and more affordable — just the way we like it. Book your seat, grab a drink, and let the curtain rise. P.S. London Calling runs only till June 22. Now’s your cue to book on www.headout.com.

What happens when Paris’ most iconic landmarks meet its finest restaurants? You get something très special. ✨ We’ve partnered exclusively with Bertrand Hospitality, the force behind some of France’s most legendary dining destinations, to bring cultural dining experiences to: 1. Palace of Versailles 2. Disneyland Paris 3. Champs Elysées 4. Opéra Garnier For the first time, these iconic venues are now bookable online, only on Headout! We’re bringing together the best of Paris — and this is only the first course. 😉 🔗 Full piece here: https://lnkd.in/gg_tTc6h

Another destination joins the Headout map. 🌎 We’re now live in Hawaii—with experiences shaped by local voices, curated by our team on the ground, and trusted by some of the island’s most iconic partners. Oʻahu today, more islands (and magic) soon. 💜