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.In this role, you will:- 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
Please apply if you have:- 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
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 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 determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. The range for this United States located role is
$180,000-200,000.
In addition to a competitive base salary, roles are eligible to be considered for additional compensation and benefits including: commission-based compensation; health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave and benefits.
