Senior Director, Ad Sales

KAYAK, part of Booking Holdings (NASDAQ: BKNG), is a leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car and vacation package. We're also transforming business travel with a new corporate travel solution, KAYAK for Business.

As an employee of KAYAK, you will be part of a travel company that operates a portfolio of global metasearch brands including momondo, Cheap flights and Hotels Combined, among others. From start-up to industry leader, innovation is in our DNA and every employee has an opportunity to make their mark. Our focus is on building the best travel search engine to make it easier for everyone to experience the world.

Kayak 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.

We’re looking for a leader who brings exceptional sales energy and a passion for winning, coupled with the analytical mindset to uncover growth opportunities, identify performance gaps, and make data-driven decisions. The ideal candidate pairs a passion for driving growth and winning business with expertise in commercial strategy, customer success, and product innovation.

This role requires you to commute to our Norwalk, CT office 3 times a week.

• 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

• Demonstrated experience in digital advertising sales, including leading and developing a sales team toward shared revenue goals
• 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 — equivalent experience in adjacent industries is warmly considered
• 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
• Experience working 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

• Work from (almost) anywhere for up to 20 days per year
• Focus on mental health and well‑being:
  • Company‑paid therapy sessions through Spring Health
  • Company‑paid subscription to Head Space
  • 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 volunteer time
• Focus on your career growth:
  • Development Dollars
  • Leadership development
  • Access to thousands of on‑demand e‑learnings
• Travel Discounts
• Employee Resource Groups
• Competitive retirement and health plans
• Free lunch 2 days per week

There are a variety of factors that go into…