FAQ | Frequently asked questions about Headroom assistance

Frequently Asked Questions

Joining Headroom

Headroom offers remote executive assistants to ambitious founders and executives who want to plug and play without hiring, training and managing headaches. With a flexible Headroom membership, you get the executive support you need, when you need it – at a fraction of the cost of a full-time assistant.

If you’d like to give yourself and your leadership some Headroom, contact [email protected] to discuss the best membership plan for you.


If you don’t have an EA, you are an EA.

While you could spend your time on growth and leadership, you are busy scrolling through your inbox, meetings, flights, processing receipts and getting the Board together for a meeting.

You can probably do all these jobs well, but isn’t it better to focus on growing yourself and your business? We believe that you should focus on what you do best and let us take care of the rest.

On top of that, compare your hourly rate with ours.

Tony Robbins said “I don’t do anything that someone else can do better, and I don’t do anything that isn’t the highest and best use of my time” and we at Headroom could not agree more.

Flexibility and education is becoming increasingly important for companies and teams. Headroom can help you with that.

Hiring a traditional, in-house assistant takes time, effort – and money. Your HR team might spend weeks hiring, on-boarding and managing. And what happens when your assistant is sick or on holiday?

Or you could simply subscribe to Headroom.

Since 2012, we have specialized in premium remote Executive Assistance. This means that we take care of the hiring, training and managing the best EAs. So you can hit the ground running with your EA team.
As a Headroom Member you’re getting more than just an extra set of hands: you’re getting our whole team dedicated to crushing your task list.

Our EAs use our proprietary software to manage their workload, securely share knowledge and efficiently hand over tasks with each other. This means that if your primary EA is sick or on vacation, we always got you covered without compromising on quality.

Last but not least, Headroom EAs are our employees, not contractors. We work together and grow together as part of a dynamic, empowering company culture.

Welcome to the future (of work)!

After you apply for one of our memberships, we will contact you within 24 hours to understand your needs and expectations. If there is a good fit, together you will choose a start date and plan a Kick-off meeting.

During the Kick-off you will meet your primary EA and discuss your tasks, preferences and goals. You do not have to prepare anything for this, your EA will guide you through it.

After the Kick-off we will activate your profile and start assisting you.

You will receive a daily overview of the open tasks and their status, plus a weekly video call to review the upcoming week, to-do’s and planning. The support team is always at hand for any feedback or questions you might have.

Read more on how to get started with Headroom.

Headroom EAs

At Headroom, we are revolutionising the world of EAs by overcoming its single point of failure: relying on one dedicated assistant, rather than a team.

That’s why we don’t assign you only one assistant, but we match you carefully with a team of EAs to support you.

This way, you always have someone who is familiar with your work style and needs who will step in and pick up your to-do list when your primary EA is away.

We are all about ongoing learning and continuous growth.

Our Headroom assistants go through an intensive training program and have access to personalized learning journeys, tailored to their level of experience and career ambitions.

We guide you through the on-boarding and set-up process and take note of your preferences and ways of working. You do not need to prepare anything for this.

Your assistant will pick up a new task within four hours. You will also get back what the status is and expected completion date. A task will never be outstanding for more than three days.

Is it a priority? We’ll pick it up immediately. Just give us a call so we can prioritise your request.

You can reach us between 09:00 and 18:00 hours Monday-Friday.

In case of an urgent issue you can contact us outside these times. You can always send a message to your EA outside of office hours. They will pick it up the next working day.

Pricing and Data

We have three types of Memberships. Find out which one is right for you:

Our Corporate Membership is a perfect fit to allow more headroom for your entire leadership team and unlock their potential. Discover more.

Our Enterprise Membership the best fit for companies looking for a total strategic business partner solution for their EA needs. This tailor-made plan starts from 25 seats. Interested? Just email [email protected] and we will connect you with one of our dedicated Account Managers. Discover more.

Our Business Membership is best suited for entrepreneurs looking for more headroom and support for themselves. You can always upgrade your individual membership as your team grows. Discover more.

Monthly subscriptions

Exclusive use per Membership seat. Each Membership seat is just for you, but if someone in your company would like to join, you can upgrade your individual Business membership to a Corporate one.

Your company’s membership renews automatically on a monthly rolling basis, subject to Headroom’s terms and conditions.

If you need to change your membership or payment method, please contact us at [email protected] or via +1 888 246 6617 to discuss your options.

We meet the most stringent requirements of the GDPR regulations and legislation both in Europe and in the US. This allows us to also assist publicly-traded companies.

We process your data via end-to-end encryption, 2-way verification log-ins and activate an account via your company’s infrastructure. So you stay in control. 

For passwords and other sensitive information, we use a secure sharing and storing password manager. This way, your data is protected at all times. In addition, all our EAs sign an NDA and agree to background checks.

We are very proud of our member community and we thoroughly process every membership application to see if there is a good value fit.

If you have colleagues, friends or peers who would like to apply for membership:

a) Let us know who your referral is. We’ll make sure to make their time worth it and take your recommendation into consideration.

b) Once we officially agree on a starting date and membership, we’d like to say thank you to both of you!

c) Every new member who came through referral gets an adjusted invoice for their first month – as a token of appreciation for their trust.

b) The person who referred a new member can choose between a donation to a charity of choice or an adjusted rate on their next invoice.

Read how our Reward scheme works.