Strategic Account Executive, Dex

Headout • New York, NY

29d • $175,000 - $275,000 • Hybrid

About The Position

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.

Requirements

• 5–8 years of enterprise sales experience
• Strong quota-carrying track record of closing meaningful, consultative deals - owning the full cycle from first touch to signature.
• Experience selling something new before, launched a product, opened a market, or created demand where none existed.
• Ability to build pipeline, playbooks, and process without waiting for someone to hand them to you.
• Ability to think strategically, prioritize well under competing demands, and bring clarity to situations where the path isn't defined.
• Ability to work well with product, operations, marketing, and leadership teams to execute sales initiatives end-to-end.
• Deep fluency with AI tools and the credibility to sell an AI product with real depth.
• Genuine curiosity about and daily use of AI.

Nice To Haves

• Experience selling into governments, universities, public institutions, or non-profits.

Responsibilities

• Own the full sales lifecycle — identifying and pitching opportunities, closing deals, and growing long-term relationships.
• Help define the commercial playbook a category-creation product deserves.
• Build from 0→1: Help define the commercial playbook, partnership strategy, and expansion opportunities from the ground up.
• Drive the full sales lifecycle, from outbound prospecting and commercial negotiations to account management and long-term growth.
• Create the need and educate buyers on a genuinely new kind of experience, rather than respond to existing demand.
• Work across international markets and collaborate closely with teams across product, growth, operations, and leadership.
• Prospect, pitch, negotiate, close, and manage accounts.

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.
• Equity through our ESOP program.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed