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KAYAK

Senior Director, Ad Sales

KAYAK

Senior Director managing North American advertising for KAYAK. Leading sales growth, team development, and strategic partnerships in digital advertising.

Posted 6/3/2026full-timeCambridge • Massachusetts • 🇺🇸 United StatesSenior💰 $195,000 - $205,000 per yearWebsite

About the role

Key responsibilities & impact
  • 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

What you’ll need
  • 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

Comp & 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
  • Fun quarterly events such as boat trips, arcades, ski trips, Thursday happy hours, and more

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools
digital advertising salesdata analysisrevenue growth strategyperformance data utilizationadvertising solutions developmentmarket insights applicationsales team leadershiprelationship management
Soft Skills
coachingcommunicationrelationship-buildingcollaborationpeople-first leadershipadaptabilityteam culture contribution