Founding Strategic Account Exec — AI Travel Platform

Headout Inc; New York (NY); Hybrid; 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

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.