Executive Assistant

Kayak; Norwalk (CT); Hybrid; USD 95,000 - 120,000; Full time

Benefits offered by this job

Work from anywhere

Company-wide week off

No meeting Fridays

Paid parental leave

Generous vacation

Volunteer time

Development Dollars

HeadSpace subscription

SpringHealth therapy

Job summary

Kayak in Norwalk, CT is seeking an Executive Assistant / Communications Specialist to support the executive team with calendar management, communications coordination, and leadership support. This role requires 3+ years in admin or executive support, exceptional organizational skills, and ability to handle confidential information with discretion in a fast-paced travel-tech environment.

The position is hybrid, based in Norwalk, with three days in the office per week, and offers benefits and

Qualifications

• 3+ years of experience in administrative, executive support, or communications coordination roles.
• Experience supporting senior leadership.
• Strong written and verbal communication.
• Ability to handle confidential information with discretion.

Responsibilities

• Own and manage complex, high-volume calendars across time zones.
• Coordinate logistics for executive meetings and offsites.
• Prepare and format presentations and briefing documents.
• Serve as liaison with stakeholders and manage correspondence.
• Track action items and ensure follow-through.
• Handle confidential information with discretion.
• Manage administrative tasks such as billing and travel.
• Anticipate executive needs and address them proactively.

Skills

Calendar management

Executive support

Communication

Discretion

Independent work

Tools

Calendar tools

Productivity software

Job description

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, Cheapflights and HotelsCombined, 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 looking for a highly organized, detail-oriented Executive Assistant (EA)/Communications Specialist to support the executive team with administrative and coordination tasks. This role sits at the center of how our executive team runs day to day: owning complex calendars, coordinating communications, and keeping the leadership team's priorities moving. The ideal candidate is a problem-solver who thrives in a fast-paced environment, exercises sound judgment with sensitive information, and can juggle competing priorities without dropping details.

Note, this position is required to work from our Norwalk, CT office 3 days per week.

What You’ll Do

• Own and manage complex, high-volume calendars for members of the executive team, including scheduling meetings across multiple time zones, resolving calendar conflicts.

• Coordinate logistics for executive/leadership meetings, offsites, and leadership gatherings, including agendas, materials, and room booking.

• Prepare and format presentations, briefing documents, and meeting notes.

• Serve as a liaison between the executive team and internal/external stakeholders, managing correspondence and follow-ups.

• Track action items and next steps from leadership meetings and ensure timely follow-through.

• Handle confidential information with discretion and professionalism.

• Manage administrative tasks (e.g billing and travel details).

• Anticipate the needs of the executive team and proactively address them.

What You Bring

• 3+ years of experience in an administrative, executive support, or communications coordination role, ideally supporting senior leadership.

• Exceptional organizational and time-management skills with a proven ability to manage complex calendars.

• Strong written and verbal communication skills, with sharp attention to detail.

• Proficiency with calendar and productivity tools

• Ability to handle sensitive and confidential information with discretion.

• A proactive, resourceful, AI-forward mindset and the ability to work independently.

• Comfort operating in a fast-paced and rapidly changing environment.

We know that no candidate will check every box. If you meet most of these criteria and are excited about this work, we encourage you to apply.

Benefits and Perks

• Work from (almost) anywhere for up to 20 days per year.

• 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

• Focus on mental health and well-being:

• Company-paid therapy sessions through SpringHealth

• Company-paid subscription to HeadSpace

COMPENSATION

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 Massachusetts -based role is $95,000-$120,000.

We offer a competitive base salary and benefits including: 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 benefits. This role is eligible to be considered for an annual bonus.

INCLUSION

At KAYAK, we want everyone to have the space to grow, share ideas and do great work. That's why we're focused on hiring the best talent from all walks of life and experiences, supporting them well and making sure no one feels like they have to fit a mold to belong here.

Need any adjustments for the interview, application or on the job? No problem – just give us a heads-up. We've got you.