Strategic Account Executive, Dex

Headout, a rapidly growing travel marketplace with over $200 million in revenue and operations in more than 700 cities, is seeking a Strategic Account Executive for Dex, their AI-powered travel companion. This role is based in New York and offers the opportunity to shape a new product category in a fast-paced, entrepreneurial environment.

As the founding commercial hire for Dex, you will be responsible for the entire sales lifecycle, including outbound prospecting, negotiations, closing deals, and managing long-term client relationships. Your efforts will directly contribute to defining the commercial strategy and partnership approach for this innovative product.

Ideal candidates will have 5–8 years of enterprise sales experience with a proven track record in consultative selling. Experience in launching new products or creating demand in untapped markets is essential. Strong strategic thinking, the ability to navigate ambiguity, and effective collaboration across functions are key to success in this role.

The compensation package includes an on-target earnings (OTE) range of $175,000–$275,000, based on experience, along with equity through the Employee Stock Option Plan (ESOP). Benefits encompass health insurance (including dental and vision), a hybrid work schedule with three days per week in the NYC office, a $250 stipend for setting up a productive work environment, $500 in Headout Credits for global experiences, unlimited learning credits for professional development, and opportunities for travel across nine global offices as needed.

Headout fosters a culture of ownership, craftsmanship, and impact, encouraging team members to do the best work of their careers. The company is committed to building a durable organization for the long term, offering significant autonomy and direct exposure to leadership, allowing you to shape how Dex evolves commercially.