Strategic Account Executive, Dex

About 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.

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.

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. You'll own the full sales lifecycle — identifying and pitching opportunities, closing deals, and growing long-term relationships, while helping define the commercial playbook a category-creation product deserves. This is a highly entrepreneurial role suited for someone who enjoys building new business lines, navigating ambiguity, and operating with high ownership in a fast-moving environment. You'll report directly to the GM, North America.

What Makes This Role Special

• Build from 0→1: You'll be the founding commercial hire for Dex, helping define the commercial playbook, partnership strategy, and expansion opportunities from the ground up.
• Own both acquisition and growth: You'll drive the full sales lifecycle, from outbound prospecting and commercial negotiations to account management and long-term growth.
• Define the category: Dex isn't another product in a crowded market. You'll create the need and educate buyers on a genuinely new kind of experience, rather than respond to existing demand.
• Operate globally: You'll work across international markets and collaborate closely with teams across product, growth, operations, and leadership.
• High ownership, direct to leadership: Reporting to the GM, North America, you'll have significant autonomy, direct exposure to leadership, and the opportunity to shape how Dex evolves commercially.

Requirements

• You've closed, consultatively and end-to-end. You bring 5–8 years of enterprise sales experience and a strong quota-carrying track record of closing meaningful, consultative deals — owning the full cycle from first touch to signature.
• You've built from zero. You've sold something new before, launched a product, opened a market, or created demand where none existed, and you know how to build pipeline, playbooks, and process without waiting for someone to hand them to you.
• 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.
• A strong plus: Deep fluency with AI tools and the credibility to sell an AI product with real depth. You don't need to be an engineer, but genuine curiosity about and daily use of AI will accelerate everything you do here.
• Good to have: Experience selling into governments, universities, public institutions, or non-profits.

Who This Role Is Not For

• 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.
• Ambiguity slows you down. Priorities will shift as we learn. If you need certainty before you can move, the pace here won't suit you.

Pay

This role has an on-target earnings (OTE) range of $175,000 – $275,000, based on the candidate's experience. You will also receive equity through our ESOP program.

Benefits

• Health insurance including dental and vision.
• Hybrid work schedule, including 3 days per week in our NYC office.
• $250 to set up a productive work environment outside of the office.
• $500 Headout Credits to head out to any of our experiences around the world.
• Unlimited Learning Credits for paid courses and sessions to aid your learning & growth.
• Travel across our 9 global offices if your role demands it.