Senior Director, Ad Sales

Job Summary

KAYAK, part of Booking Holdings (NASDAQ: BKNG), is seeking a dynamic and commercially driven Senior Director, Ad Sales to lead our North American advertising business. This is a highly visible leadership role responsible for driving revenue growth, developing high-performing sales and account management teams, and influencing the future of our advertising products.

Key Responsibilities

• Lead, coach, and develop a high-performing ad sales team, creating an environment where people can grow and do their best work
• Own and grow KAYAK's North American advertising revenue, setting ambitious goals and driving the team to deliver against them
• Build and sustain strong, trust-based relationships with advertising partners, agencies, and travel brands
• Collaborate closely with product, marketing, and commercial partnerships teams to develop compelling, data-informed advertising solutions that meet partner needs
• Use performance data and market insights to identify opportunities, refine strategy, and communicate results clearly to senior leadership and partners
• Represent KAYAK externally at industry events, partner meetings, and business reviews, serving as an expert ambassador for KAYAK's advertising offering
• Work cross-functionally with the broader NORAM commercial team to align ad sales efforts with KAYAK's overall regional strategy
• Contribute to a collaborative, inclusive team culture that reflects KAYAK's values

Requirements

• Demonstrated experience in digital advertising sales, including leading and developing a sales team toward shared revenue goals
• A strong understanding of the digital advertising ecosystem and evolving industry trends
• A track record of building and growing advertiser or agency relationships, ideally in a travel, media, or technology environment
• The ability to use data to understand performance, identify opportunities, and tell a clear story to partners and internal stakeholders
• Strong communication and relationship-building skills, with comfort engaging both external partners and internal cross-functional collaborators
• The ability to work in a fast-moving environment where priorities shift and cross-team collaboration is essential
• A thoughtful, people-first approach to leadership — you care about the growth and wellbeing of the people you work with

Benefits and Perks

• Work from (almost) anywhere for up to 20 days per year
• Focus on mental health and well-being: Company-paid therapy sessions through SpringHealth, Company-paid subscription to HeadSpace, Company-wide week off a year - the whole team fully recharges (and returns without a pile-up of work!)
• No meeting Fridays
• Paid parental leave
• Generous paid vacation + time off for your birthday
• Paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays)
• Parental leave and benefits
• Free lunch 2 days per week
• Fun quarterly events such as boat trips, arcades, ski trips, Thursday happy hours, and more