Holiday Management | EAs to manage your time off | Headroom

Sit back, relax and enjoy the journey

Let Headroom Executive Assistants plan the perfect holiday & travel

Learn how to start


Executive playing with his two children
Allow yourself to enjoy what you've built

When was the last time you treated yourself to a holiday? We will:

  • Provide a full travel plan and personalized options for you and your family
  • Book flights and accommodation based on your preferences
  • Find the best solutions to any delay or last-minute changes
  • Negotiate best rates and deals
  • Help you choose the best insurance option
  • Ensure your bucket list is all ticked off by the end of the trip

All you have to do is give the go-ahead and pack your suitcase when it’s time to go.

Smiling businessman sitting in office setting, talking on the phone

Think about all the tasks we can do, and more


Inbox, calendars, travel, to-do lists, goals and teams

Questions? See all FAQs

With our proven Inbox Zero method:

  • We process your inbox twice a day and provide a clear to-do list organized by priority
  • Calendars are synchronized more efficiently
  • You receive reminders for important emails
  • We unsubscribe you from and clean up unwanted e-mails
  • Review weekly & long-term goals
  • Realize your ideal working week with fixed focus and meeting days
  • Handle all scheduling requests
  • Coordinate internal and external scheduling
  • Organize one-time and recurring events
  • Manage cancellations and rescheduling
  • Create travel itineraries and add them to your calendar
  • Book all travel and accommodations
  • Find the hottest local hotels, bars, restaurants and museum based on our EA knowledge wiki
  • Make restaurant reservations based on your preferences

You will know exactly where to be, when, and how best to get there. We will also make sure that your boarding passes and other important documents are always easily available. And don’t worry about incoming calls or emails during your trip… we will take care of it.

  • Take notes during important team/board meetings
  • Keep time and ensure agenda is followed
  • Follow up with worked-out notes & action lists
  • Save and organize documents & contracts
  • Manage expense tracking
  • Process business cards

Work-Life Balance

Personal tasks to help your team balance their work and life to unlock their best selves.

See membership plans

Whether you are looking for the best nanny, a reliable plumber or a new gym, we are at your side. Finding the right supplier often takes more time than you think.

With years of experience in the field, we know many of the best services around and would love to find the right one for you.

We will provide you with a travel plan and options most suitable to your needs and preferences to ensure your weekend getaways and trips are as perfect as they should. All you have to do is give the go-ahead and pack your suitcase when it’s time to go.

A wedding, the birth of a child or a 20-year anniversary are special moments in one’s life and they are worth celebrating. But with all the pressure of day-to-day work it can be very tricky to think of the perfect gift. Your Headroom EA can help you with this.

Get started

Start working with our Executive Assistants – with 3 simple steps

Entrepreneur talking to assistant over video call
Step 1

Interested in becoming a Member?

Headroom gives you access to an exclusive community of worldwide successful CEOs and entrepreneurs who share values and a similar work ethics. You can schedule a 30-min. consultation to discuss needs, questions and see if there is a good fit. Afterwards, you can apply for one of our memberships.

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Step 2

See our pricing

Once your membership application has been accepted, we will assemble your dedicated EA team and introduce them to you and your team. Next to that, you will discuss your profile, goals, tasks, preferences and other important information during a Deep Dive. You don’t need to prepare this, we got it.

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Step 3

Access. Deep Dive. Go!

You activate a business email account with Teams or Slack for your new EAs to work and communicate from with you and your team. This enhances team work, communication and data security. Once your Headroom EA has access, we start crushing your to-do list within 24 hours.

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Let's talk possibilities