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Senior IT Support Engineer



IT, Customer Service
Cambridge, MA, USA
Posted on Thursday, November 9, 2023

KAYAK, part of Booking Holdngs (NASDAQ: BKNG), is the world’s leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car, cruise, or vacation package. We’re also transforming the in-travel experience with our app and new accommodation software. For more information, visit

As an employee of KAYAK, you will be part of a global network that includes OpenTable and KAYAK's portfolio of metasearch brands including Swoodoo, checkfelix, momondo, Cheapflights, Mundi and HotelsCombined. Many employees are dedicated to one brand, but we all have the benefit of using each others strengths and insights. Together, we're able to help people experience the world through dining and travel.

The Senior IT Support Engineer will be a member of the team responsible for configuring and supporting end user computers and corporate IT services at, a worldwide leader in Internet travel search. This is a phenomenal opportunity for the right candidate to gain hands-on experience in a dynamic Internet company! The ideal candidate is motivated by new challenges, collaborative and effectively communicates in a distributed team environment.

This role will be required to rotate working in our two Massachusetts offices (Cambridge & Concord) 4 days per week.

In this role, you will be responsible for:

  • Employee lifecycle management (onboarding and offboarding)
  • Managing the helpdesk ticketing queue, resolving requests in a timely manner.
  • Supporting our employees both in office and remotely.
  • Deploying new software and hardware to our employees using MDM tools.
  • Configuring and maintaining office hardware like printers, company dashboards, room display tablets, video conferencing equipment.
  • Provide technical support for large scale meetings.

Please apply if you have:

  • Strong troubleshooting skills with both Windows and macOS.
  • Strong multitasking and prioritization ability.
  • Knowledge of IT Security best practices.
  • Knowledge of networking such as TCP/IP, DHCP and DNS.
  • 3+ years of proven work in IT helpdesk in a Mac / Windows mixed environment.

And experience with the following:

  • Google Products and Services.
  • Cloud based applications.
  • Windows Server Active Directory users and computers.
  • Terminal and Powershell, and scripting languages.
  • MDMs, like JAMF and InTune
  • Identity Management platforms, like OKTA.

Benefits and Perks

  • 4 weeks paid vacation
  • Day off on your birthday
  • Generous retirement plans
  • Awesome health, dental and vision insurance plans
  • Flexible Spending Accounts
  • Headspace Subscription
  • No Meeting Fridays
  • Drinks, coffee, snacks, games etc.
  • Weekly catered lunches
  • Flexible hours
  • Regular team events/excursions
  • Universal Paid Parental leave

Diversity and Inclusion

We aspire to have a workplace that reflects all of the diverse communities we serve. We know that when we have diverse teams we produce more creative ideas, products, and better outcomes for our team members. OpenTable/KAYAK is proud to be an Equal Opportunity Employer and we welcome and encourage candidates from all backgrounds and experiences to apply for roles on our team. Whoever you are, just be you!

We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform job responsibilities, and to receive other benefits and privileges of employment. Please contact us to request accommodation.