Hire your executive assistant in Chicago
Get things done with our Personal Assistants,
trained and employed by us
Chicago is quickly becoming a startup hub recognized around the world,
with a thriving community of entrepreneurs and businesses popping up all over the city. From tech startups to creative agencies and everything in between, Chicago is a hotbed of innovation and growth.
As more and more startups and businesses emerge in Chicago, it’s more important than ever for founders and executives to work with the right team and get the right assistance to fully unlock the possibilities for their business.
This is where our team of experienced and professional assistants comes in.
We help simplify and organize, so you can focus on the important things
Plug & Play
Headroom makes it easy with monthly, flexible memberships to our remote Personal Assistant service. Our personal executive assistants are trained, managed and employed by us so you don’t have to add them to your payroll. You can plug-in and start playing, we’ll take care of the rest.
Our team of educated and ambitious personal assistants are up to 25% faster than traditionally trained PAs. Which means more tasks get completed per hour and your life gets easier.
EU & US continuous support
Our network of personal assistants use proprietary software that allows them to securely share knowledge with each other. When you start the week in Chicago and finish it in Paris, your PA team will match your area & Chicago time zone.
Members at Headroom have access to a private network of highly successful entrepreneurs & C-suites in Chicago and beyond looking to unlock possibilities and build new connections.
How it works
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.
Apply for membership
Once your membership application has been accepted, we will assemble your dedicated personal assistant 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.
Access. Deep Dive. Go!
You activate a business email account with Teams or Slack for your new PAs to work and communicate from with you and your team. This enhances team work, communication and data security. Once your Headroom personal assistant has access, we start crushing your to-do list within 24 hours.
All our plans are packed with
- Expert Assistance Mo-Fr from 09:00 – 18:00 hours
- Continuous support / Assistant holiday and sickness cover
- Weekly reporting & overview
- Best practices by our community
- Seamless communication via video email chat notion and phone
- Access to Headroom’s collective expertise
- Up to one extra day per week freed up
Think about all the tasks we can do, and more
Inbox, calendars, travel, to-do lists, goals and teams
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
Personal tasks to help your team balance their work and life to unlock their best selves.
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.
We're really good at this, because we've been doing it for 10 years.
We created the world’s 1st platform for personal assistants to take them to the next level. Thanks to our proprietary software & Academy, Headroom PAs can securely manage their work, share knowledge and keep learning.
Consistently exceeding expectations
MilanCo-CEO & co-Founder Otrium
Global PA support for Leadership Team
Cross-functional support between demand work & personal life
More creative time
Got any questions?
Headroom is a global, exclusive EA platform for ambitious and diverse members to grow, connect, have fun, and make an impact. From the beginning, and throughout our 10-year history, our EAs and members have always been at the heart of everything we do.
If you would like your brand to be part of our member benefits offering, you can contact [email protected] to discuss your options.
If you don’t have a PA, you are a PA.
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 & Education is becoming increasingly important for companies and teams. Headroom helps with that.
Hiring a traditional, in-house assistant takes time, effort – and money. Plus, what happens when your Assistant is sick or on holiday?
Your HR team might spend weeks hiring, on-boarding and managing.
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 PAs. So you can hit the ground running with your EA team in no time.
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 PAs use our proprietary software to manage their work-load and securely share knowledge and efficiently hand over tasks with each other. This means that if your primary PA is sick or on vacation, we always got you covered without compromising on quality.
Last but not least, Headroom PAs 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, our Sales agent 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 Deep Dive with your PA.
During the Deep Dive you will meet your PA team and discuss your tasks, preferences and goals. You do not have to prepare anything for this, your PA will guide you through it.
After the Deep Dive we will activate your profile and start assisting you!
You will receive a daily task overview, plus a weekly video call to review the upcoming week, to-do’s and planning. Our Support team is always at hand for any feedback or questions you might have.
Headroom personal assistants
At Headroom, we are revolutionizing the world of PAs 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 PAs to support you.
With our best-in-class continuous executive assistance, we ensure a consistent quality of service. We never leave you uncovered, we 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.
Headroom personal assistants are remote but US-based and local to your timezone. We currently offer our virtual executive assistance service in the following cities within Eastern Time zone (ET): Atlanta, Baltimore, Boston, Charlotte, Cincinnati, Cleveland, Columbus, Detroit, Durham, Fort Wayne, Greensboro, Hempstead, Indianapolis , Jacksonville, Jersey City, Lexington, Louisville, Miami, New York, Newark, Philadelphia, Pittsburgh , Raleigh, Virginia Beach and Washington D.C.
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 PA 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 (Tech) Entrepreneurs looking for more headroom for themselves. 1 seat only. Discover more.
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 PAs 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, they can add your name and email address to the application form. We’ll be in touch to confirm we have received their application and take your recommendation in consideration.