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Account Executive, Leisure Travel

Oversee (Formerly Fairfly) - United States - In-office - posted 2026-09-07

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Salary: USD 180,000 - 240,000 / annual

Oversee is a travel technology company using AI and automation to solve complex challenges across the travel ecosystem. The company has built technology used by Fortune 500 travel organizations and is now expanding into the leisure travel market with exponential YoY revenue growth. This Account Executive role is not a traditional territory-based position. You will help build an entirely new market for Oversee's air and hotel reshopping technology, selling 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 determine market positioning, target segments, and the leisure go-to-market motion. Key responsibilities include: - Own the full sales cycle from prospecting through close for the leisure travel business - Build relationships with senior executives and decision-makers across OTAs, leisure agencies, tour operators, and vacation providers - Build and maintain a strong pipeline of qualified leisure travel opportunities - Define and refine the leisure ideal customer profile (ICP), positioning, messaging, and value proposition - Identify segments, accounts, and use cases with strongest product-market fit - Lead complex enterprise sales processes involving commercial, technology, operations, product, finance, and executive stakeholders - Partner with Product and Engineering to bring market intelligence into product and GTM strategy - Turn early customers and market learnings into a repeatable sales motion for the leisure vertical This is an opportunity to join early in a significant market expansion, help bring a new solution to market, and play a key role in building Oversee's presence in the leisure travel segment. The role requires someone who already knows the leisure travel market deeply and can bring that knowledge and network from day one. REQUIREMENTS: - 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 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 ability to build compelling ROI and business cases for customers - Independent, entrepreneurial mindset and comfort building a market without an established playbook - Experience being an early or first AE at a startup or scale-up is a strong plus

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