How to hire the perfect executive assistant | Hire assistance today

How to Find and Hire the Perfect Executive Assistant: Everything You Need to Know

Executive Assistant and Executive shaking hands after hiring an executive assistant

As a busy founder in a growing startup, your time is valuable. There are hundreds of emails to read, hours of meetings to attend, and you’re constantly keeping one eye on your balance sheet and the other on your growth metrics. Everything you do is important, but it’s crucial to remember that you don’t have to do it all yourself. That’s where hiring a virtual executive assistant (EA) comes in.

A good remote EA will lighten your load, freeing time to focus on the most critical aspects of running your business and keep a clear overview of your priorities. But how do you find the right person for the job?

This article will show you how to find and hire the perfect virtual assistant for you, whether you’re a young startup in its early stages or a fully scaled operation that’s just secured its Series B funding. 

Here’s what we’ll cover:

  • Why hire a remote executive assistant?
  • What qualities to look for when hiring an executive assistant
  • How to find and hire a virtual executive assistant

Why hire a remote executive assistant?

Hiring a virtual assistant can be a godsend for busy CEOs, founders, and leaders. An EA provides much-needed support with tasks like meeting scheduling, email management, travel planning, and more.

But they’re also not just a personal assistant. Most executive assistants provide high-level administrative support for the companies they work for, including analyzing reports, conducting research, managing projects or workflows, and even attending meetings on an executive’s behalf. 

This combination of high-level professional skills and humbleness to work behind the scenes (for the most part) is rare, which is why finding the right executive assistant to hire can be hard.

But, as we like to say at Headroom if you don’t have an executive assistant, you are an executive assistant. So, read on for tips on how to find that magic mix of skills.

What qualities to look for when hiring an executive assistant

When you’re hiring an executive assistant, there are certain qualities you should always look for, no matter which industry you work in.

Time management

The most important quality an executive assistant should have is the ability to be organized and efficient. An EA should be able to keep track of your schedule and make sure that everything runs smoothly. They should also be able to handle a lot of correspondence and act as a point of contact for you with other people or businesses.

Which leads us to…


Communication skills are essential as an EA will often have to relay messages from you to your colleagues and employees or, on the rare occasion, even represent you in meetings. You will want to make sure that your messages are delivered accurately and correctly to avoid any unnecessary misunderstandings.


An empathetic executive assistant can make all the difference. Once they get to know you, they should be able to put themselves in your shoes and anticipate your needs, completing tasks before you even know you need them completed.

Attention to detail

As the company founder, you need to focus on the big picture. Your executive assistant should focus on the nitty-gritty details.

This includes phone numbers, email addresses, spelling errors, reservation times, important dates, and more – all the items that may otherwise take up precious space in your brain (where your next great business idea might come from, after all).

It’s not that these detail-oriented, administrative tasks are less important. In fact, they are likely the tasks that keep your company functioning and moving forward. This is why it’s even more important to assign them to someone who excels at them.


An executive assistant often acts as a gatekeeper for access to you and your time, which is very valuable. For this reason, you want to hire someone confident in saying ‘no’ to requests that aren’t worth your time and someone who can make that call confidently on their own.

Assertiveness comes in handy in many other scenarios too, including keeping projects on task, representing your vision in meetings, talking to customer service when travel plans fall through, etc.


Since you’ll be working so closely with your executive assistant, you’ll want to hire someone who maintains a high level of discretion and confidentiality. They will often have access to private information that, if leaked, could jeopardize you or your company’s future. Don’t trust just anybody in this position.

How to find and hire a virtual executive assistant

Now that you know the qualities of a good executive assistant, how do you actually find the person who possesses them?

Here are a few tips on how to find an executive assistant who will match your expectations and bring the biggest ROI:

1. Take time to assess your needs

What exactly do you need help with? Make a list of tasks that you’d like your assistant to handle. This will give you a better idea of the skill set required for the position.

It will also help you decide if you need a dedicated full-time assistant that is trained to work with you long-term or if you could manage with less expensive, agency-based assistance. Or you might find out you actually need a Chief of Staff rather than an EA. More on that in the following points.

2. Brief your HR team and allocate resources for recruiting

If you want to hire an in-house, full-time executive assistant, you should work with your Human Resources department to write a job description that attracts the right candidate.

Here are some potential duties and responsibilities you could delegate:

  • Managing all incoming and outgoing communications on behalf of the executive, including emails, phone calls, direct messages, etc.
  • Organizing important documents, such as reports, meeting notes, emails, and letters
  • Updating the executive’s calendar, including adding events, rescheduling appointments, and providing daily briefings
  • Being the point of contact for internal and external contacts, including vendors, colleagues, clients, and customers

Your HR team might want to browse a few executive assistant job descriptions online first. 

You’ll need to free yourself up to support interviewing, hiring, and onboarding—after all, you’ll be working closely with this recruit, and will need to ensure they’re the best fit for the job. You’ll also need to block out time in your calendar to train them. 

Hiring in-house is a more traditional way of hiring an executive assistant, and you’ll need to be mindful of the time this will take away from your already busy schedule.

However, you should opt for an in-house hire if you have more than enough work and budget for a full-time role and if you have IT or confidentiality constraints that prevent you from outsourcing the work. But know that, like hiring any full-time employee, hiring an in-house EA comes with its own risks.

3. Try a temporary agency

A temporary agency that specializes in executive assistants could be helpful if you want to hire an executive assistant for a short-term project or a freelance gig. You could even use it to try out what it would be like to have an executive assistant before you decide to commit to one full-time.

The plus side of working with an agency? There will always be someone available to assist you, even if your regular assistant is on sick leave or vacation. 

On the other hand, it might not always be the same person who works with you each time. This is because temporary agency EAs are often contractors and not part of an established team, so there might be unlimited employee churns and turnarounds that mean you’ll have to start from scratch with every new assistant.  

4. Try a freelancer

There are many freelance executive assistants on websites like UpWork or WorkHopper, and many are experts at what they do.

Like a temporary agency, this solution is best used for short-term projects or part-time work with some flexibility built-in. For example, perhaps you just need someone to help you get a big launch past the finish line. Or you only need someone to handle 5 hours worth of administrative tasks per week (vs. 40).

This is a flexible, less expensive option than working with an agency or hiring in-house. But, you may struggle with reliability, confidentiality, and a less experienced pool of candidates.

X 31
What are the options when looking to hire a virtual executive assistant? We summarize them here.

5. Work with a remote executive assistant from a service like Headroom

All previous options for finding an EA require you and your HR department to still be heavily involved with the hiring process. If you decide to work with contractor virtual assistants or hire an assistant in-house, your HR team might spend weeks hiring, on-boarding and managing.

You could optimize your onboarding process with our in-depth guide. Or you could simply subscribe to a remote EA service like Headroom.

A remote executive assistance service provides access to a virtual network of experienced EAs who can work for you from anywhere, without having to add anyone to your payroll.

A good one like Headroom will hire, employ, train, and manage their EAs to provide you with best-in-class continuous care and a team who’s dedicated to crushing your business and administrative tasks while building collective knowledge that makes them perform more efficiently.

Does your work often take you to different time zones? Our team of EAs use proprietary software that allows them to securely share knowledge with and learn from each other. When you start the week in New York and finish it in Paris, your EA team will match your area and time zone.

We might be biased, but we believe Headroom blends the best of both worlds. You get the long-term relationship of an in-house hire with the flexibility and continuous support of a temporary agency.

Learn more about how the onboarding at Headroom works.

How can you stay organized and seize opportunities at industry events email header 5 2
Back to overview