The roleDex 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.
You are a great fit if- 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.
You are not a great fit if- 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.
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, you guessed it, 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.
