Leisure Travel Sales Executive - Oversee

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 Our advanced technology and machine learning eliminate outdated, manual processes that hold companies back, driving cost savings, improving efficiency, and enabling smarter decision-making.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?

This is not a traditional territory-based AE role. You’ll help build an entirely new market for Oversee, selling our air and hotel reshopping technology across the leisure travel ecosystem, including OTAs, leisure travel agencies, tour operators, vacation providers, and other high-volume travel businesses.

You’ll own deals end-to-end while helping us determine where we win, who we should target, how we position the product, and what the leisure GTM motion should look like.

We’re looking for someone who already knows this market. You understand the players, decision-makers, technology landscape, and economics of leisure travel and can bring that knowledge and network to Oversee from day one.

Come shape the future of business travel with us!

What You’ll Do:

• Own the full sales cycle for Oversee’s leisure travel business, from prospecting through close;
• Build relationships with senior executives and decision-makers across OTAs, leisure agencies, tour operators, vacation providers, and other travel businesses;
• Build and maintain a strong pipeline of qualified leisure travel opportunities;
• Help define and continuously refine our leisure ICP, positioning, messaging, value proposition, and sales motion;
• Identify the segments, accounts, and use cases where Oversee has the strongest product-market fit;
• Lead complex enterprise sales processes across commercial, technology, operations, product, finance, and executive stakeholders;
• Partner closely with Product and Engineering to bring market intelligence back into our product and GTM strategy;
• Turn early customers and market learnings into a repeatable sales motion for the leisure vertical.

About You:

• 5+ years of B2B technology sales experience, with a strong track record of owning and closing complex enterprise deals;
• Significant experience selling technology into the leisure travel industry;
• Strong relationships and experience across OTAs, leisure travel agencies, tour operators, vacation providers, or other leisure travel businesses;
• Deep understanding of the leisure travel ecosystem, including its key players, decision-makers, business models, technology landscape, and buying processes;
• Proven ability to prospect and create opportunities from scratch rather than relying primarily on inbound leads;
• Experience navigating complex, multi-stakeholder enterprise sales cycles and working with technical stakeholders;
• Strong commercial instincts and the ability to build compelling ROI and business cases for customers;
• Independent, entrepreneurial, and comfortable building a market without an established playbook.

Experience being an early or first AE at a startup or scale-up is a strong plus.

You’re a hunter and a market builder. You know the leisure travel industry, have relationships within it, and are excited by the opportunity to help Oversee build an entirely new business from the ground up.