Explore the world's best experiences - from expert-led tours and incredible landmarks to activities and events. Book tickets at the lowest prices and best deals. Backed by 500 Global.
About the role
Dex is Headout's AI-powered travel companion that transforms how visitors experience the world's most iconic venues. It's a new kind of product in a market that doesn't have a playbook yet, and we're looking for a Strategic Account Executive in New York to take it to market and own net-new revenue from day one.
What they're looking for
- You bring structure to ambiguity. You think strategically, prioritize well under competing demands, and bring clarity to situations where the path isn't defined
- You collaborate across functions. You work well with product, operations, marketing, and leadership teams to execute sales initiatives end-to-end
- Good to have: experience selling into governments, universities, public institutions, or non-profits
- You need an established playbook. There's no inbound engine, no battle-tested pitch deck, and no predecessor to learn from. If you do your best work inside a mature team, this role might not be the right fit
- You prefer to sell into existing demand. Buyers don't know they need Dex yet. If educating the market and helping create a category doesn’t excite you, this probably isn’t the role for you
- You want a narrowly-scoped closing role. You'll prospect, pitch, negotiate, close, and manage accounts, all of it
More about this role
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.
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.
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.
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...
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