Strategic Account Executive, Dex

Headout Inc; New York (NY); On-site; USD 175,000 - 275,000; Full time

Benefits offered by this job

Health insurance

Hybrid schedule

Headout credits

Learning credits

Workstation stipend

Job summary

Headout Inc. in New York seeks a Strategic Account Executive to own the full sales lifecycle for Dex, Headout’s AI-powered travel companion. You will lead outbound prospecting, close deals, and nurture long-term relationships, shaping the commercial playbook for a category-creating product.

You’ll drive acquisition and growth across international markets with high ownership and direct interaction with leadership, leveraging AI tools to accelerate sales.

Qualifications

• 5–8 years of enterprise sales experience with a proven quota-carrying track record.
• Experience building and launching new products or markets from zero.
• Ability to bring structure to ambiguity and operate with strategic clarity.

Responsibilities

• Own the full sales lifecycle from outbound prospecting to closing and long-term account growth.
• Build pipeline, playbooks, and process to scale new business.
• Collaborate across product, operations, marketing, and leadership to drive initiatives.
• Educate buyers on a genuinely new kind of AI-powered travel experience.

Skills

Enterprise sales

New business development

Category creation

AI tools fluency

Job description

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.

Our 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.

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 01: 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.

EEO statement

At Headout, we don’t just accept differences — we celebrate it, we support it, and we thrive on it for the benefit of our employees, our partners, and the community at large. Headoutprovidesequal employmentopportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. During the interview process, if you need assistance or an accommodation due to a disability, you may contact the recruiter assigned to your application or email us at [e-mail] .

Privacy policy

Please note that once you apply for this job profile your personal data will be retained for a period of one (1) year. Headout shall process this data for recruitment purposes only. Once the relevant job profile is filled or once the time period of one (1) year from the date of the job application has passed, whichever is later, Headout shall either delete your data or inform you that it shall keep it in its database for future roles. In compliance with the relevant privacy laws, you have the right to request access to your personal data, to request that your personal data be rectified or erased, and to request that the processing of your personal data be restricted. If you have any concerns or questions about the way Headout handle your data, you can contact our Data Protection Officer for more information.