Head of Sales (AgentSee) - 0-to-1 Opportunity

About Oversee:

At Oversee, we are reimagining how corporate travel is managed. Our advanced technology and machine learning eliminate outdated, manual processes that hold companies back, driving cost savings, improving efficiency, and enabling smarter decision-making.

We combine travel analytics with actionable insights, giving global enterprises the tools to gain visibility into their travel spend while continuously optimizing their programs.

We are the global leader for air and hotel reshopping solutions and also provide “AgentSee,” an AI-powered productivity tool designed to help Travel Management Companies (TMCs) work smarter and faster. AgentSee automates manual tasks like processing traveler emails, booking flights, and managing travel arrangements, enabling TMCs to reduce costs and improve service quality.

If you are looking for a dynamic, fast-paced, and positive environment and want to help solve a $17B global problem, Oversee is the place to build, grow, and make an impact. We’re growing fast, with exponential YoY revenue growth and partnerships with some of the world’s largest Fortune 500 companies.

Why Join Oversee?

We’re looking for our first Head of Sales dedicated to AgentSee. This is a true 0-to-1 opportunity. Initially, you’ll be the primary salesperson for the business, working directly with our CRO to identify where AgentSee wins, refine our ICP and positioning, close our first wave of strategic customers, and turn those learnings into a repeatable GTM motion.

As the business scales, you’ll build the sales organization around it. You’ll have significant influence not only over how we sell, but also over what we build. You’ll work closely with Product, Engineering, Marketing, and Customer Success, bringing customer and market insights directly into our product and GTM strategy.

Come shape the future of business travel with us!

What You’ll Do:

• Own and build the GTM and sales strategy for AgentSee;
• Personally lead and close early strategic enterprise opportunities, from discovery and demos through pilots, negotiation, and close;
• Define and continuously refine our ICP, positioning, messaging, pricing, packaging, and sales process;
• Translate agentic AI and complex technology into clear business value for senior enterprise buyers;
• Use customer conversations and market data to identify where we have the strongest product-market fit and what we need to build to win;
• Build a repeatable sales methodology, operating cadence, and GTM playbook;
• As the business scales, hire, develop, and lead the AgentSee sales organization;

About You:

• 8+ years of B2B technology sales experience, with a strong track record of personally owning and closing complex enterprise deals;
• Proven experience building a GTM motion from the ground up, taking a new product or business from early customers toward a repeatable sales motion;
• Experience selling AI, SaaS, automation, workflow, data, or similarly technical solutions to enterprise customers;
• Strong understanding of AI and ability to translate complex technology into measurable business value;
• Experience building and leading sales teams, with the willingness to remain hands-on and personally sell as AgentSee scales;
• Commercially sharp, analytical, and comfortable operating when the ICP, product, messaging, and playbook are still evolving;

MEDDPICC, Force Management, or similar enterprise sales methodologies are a plus. Travel technology or TMC experience is also a plus.

You’re a builder at heart, genuinely curious about AI and technology, and excited by the opportunity to turn an emerging product into a meaningful business.