Meanwhile, the product roadmap you promised the team is still a rough draft. Somewhere between the calendar and the inbox, your actual job got squeezed out.
That's usually the moment founders start asking where to hire an executive assistant. This guide walks through the options, what each one costs and how to find someone who takes work off your plate instead of adding to it.
Key Takeaways
- Define the support you need before you start searching, starting with a one-week log of your admin time.
- You can hire through job boards, freelance marketplaces, managed assistant services or placement agencies, and each one shifts screening and management differently.
- Compare total cost, not just the hourly rate, including fees, minimum commitments and the time you'll spend managing.
- Screen for judgment with realistic scenarios, because software skills are easier to teach than discretion.
- Use delegated access instead of shared passwords and onboard with a written 30-60-90 day plan.
Why Hiring an Executive Assistant Pays Off
The biggest benefit is simple: you get your time back. A good executive assistant handles the coordination that eats your week, so your hours go to product, customers and fundraising.
They also become your professional representative. Investors, candidates and partners often hear from your assistant before they hear from you, so the right hire reflects how your company operates.
Over time, a strong assistant acts like an operator. They spot a board meeting colliding with a launch week, flag the preparation load and suggest a fix before it turns into a fire drill.
Types of Executive Assistant Roles to Consider
Before you search, decide what kind of support you actually need. Most founders land on one of three options.
Full-time in-house executive assistant. This person works on-site and supports you every day. It's the deepest form of support, but you'll also cover salary, benefits, payroll taxes and equipment.
Remote or fractional executive assistant. This person works virtually, often for a set number of hours each month. You get executive-level support without a full-time salary, though in-person tasks are off the table.
General virtual assistant. A VA usually handles defined tasks such as data entry or routine scheduling. It's a lighter-weight option that works well once you know exactly which tasks to hand off.
Where to Look for Executive Assistant Talent
This is where most founders get stuck. Here are the main places to hire, along with what each one means for screening and management.
Job boards and LinkedIn. Posting on LinkedIn or Indeed can bring in a high volume of applicants. LinkedIn also lets you search for working executive assistants and reach out directly, but screening, payroll and compliance all sit with you.
Your founder and investor network. Ask founders at a similar stage who they've worked with and whether they'd hire that person again. Some investors also share referral lists for service providers with their portfolio companies.
Freelance marketplaces. Platforms such as Upwork let you contract with individuals directly. You choose the candidate, negotiate the scope and manage the work, so access controls and backup coverage are your responsibility.
Managed assistant services. These providers match you with an assistant and may include supervision and backup coverage. Prialto, for example, sells support in 55-hour monthly units that include an engagement manager and trained backup assistants.
Placement agencies. A placement agency sources and screens candidates, and you hire the assistant directly. Agencies such as Remote Leverage recruit from Latin America and the Caribbean, the Philippines, South Africa and Egypt, charge a one-time placement fee and include a 12-month replacement guarantee with no long-term contract.
Whichever route you choose, confirm pricing, minimum commitments, working-hour overlap and replacement terms in writing before you sign.
What to Consider When Hiring a Remote Executive Assistant
Hiring remotely means you can't rely on in-person cues. A few areas deserve extra attention.
Time zone overlap. Decide how many working hours need to overlap with yours. Then set clear expectations for response times on email, chat and urgent requests.
Data and access security. Use delegated permissions rather than shared passwords. Gmail supports mailbox delegation, and Google Calendar and Outlook both let you share calendars with defined permission levels.
Tools. Confirm candidates are comfortable with the tools your team already uses, such as Google Workspace, Microsoft 365, Slack or your project tracker. Build in time to train them on anything new.
Employment structure. Worker classification depends on the actual working relationship, not just the contract title. Overseas hires can also raise local employment and tax questions, so get qualified advice for the arrangement you choose.
How Much Does It Cost to Hire an Executive Assistant?
Costs vary widely by model, hours and experience. Treat the figures below as published starting points to confirm before you budget.
| Option | Published pricing to verify | Best for |
|---|---|---|
| In-house executive assistant | Salary plus benefits, payroll taxes and equipment | Founders who need daily, in-person support |
| Freelance marketplace (Upwork) | Freelance VAs charge an average of $18 to $35 an hour, per Upwork's cost guide | Founders who want to screen and manage directly |
| Managed service (Prialto) | From $1,500 a month per 55-hour unit, plus a $250 setup fee and a 90-day minimum | Teams that want supervision and backup coverage |
| Fractional EA service (Boldly) | From $2,600 a month for 40 hours | Founders who want experienced part-time support |
| Hourly plan (Time etc) | $2,160 a month for 60 hours | Steady part-time needs with a set monthly allowance |
| Placement agency | One-time placement fee plus the assistant's pay | Founders who want recruiting help and a direct hire |
For an in-house comparison, a $75,000 annual salary alone works out to $6,250 a month before benefits and taxes. Compare totals against the hours and coverage you actually need, not just the lowest rate.
How to Hire the Right Executive Assistant
Great executive assistants combine proven experience with trustworthiness. Your interviews should test both.
Focus on Detailed Experience
Listen for specific stories about past roles. The strongest candidates can explain how their responsibilities grew, which complex projects they managed and how they represented the executives they supported.
Run Two Interviews
Keep the first one conversational. Ask what they took on in their last role, how they handle private information and how they'd approach speaking on your behalf.
Use the second interview for realistic scenarios. Share a sample calendar and ask what they would change and what they'd ask you first.
Try a few "what would you do" questions:
- An investor asks for a meeting during a protected focus block. How would you handle it?
- I forward you an email with no instructions. How do you figure out what's needed?
- Two board members want to move a meeting into a travel week. How would you resolve it?
Listen for clarifying questions and clear tradeoffs. If you assign a short work exercise, pay for the candidate's time and use the same criteria for everyone.
How to Write a Strong Executive Assistant Job Description
A clear job description attracts candidates who fit the role and filters out those who don't. Cover these five elements:
- A clear title. Name the role and who it supports, such as "Executive Assistant to the CEO."
- Key responsibilities. List outcomes, not just tasks, like protecting three focus blocks a week or keeping investor updates on schedule.
- Required skills and experience. Separate must-haves from nice-to-haves.
- Why the role is worth taking. Explain the growth opportunity, such as moving into operations as the company scales.
- The work arrangement. State whether the role is remote or in-office, the hours you need and the compensation range.
Best Practices for Onboarding an Executive Assistant
How you onboard shapes how quickly your assistant can take real work off your plate. The goal is to onboard new hires so they can find answers without asking you every time.
Use the first 90 days to build that independence:
- Days 1 to 30: Set up delegated access, write down your calendar rules and walk through representative emails to explain priorities and tone.
- Days 31 to 60: Hand off one recurring process end to end, such as interview scheduling or investor update coordination.
- Days 61 to 90: Compare your calendar with the week you tracked before hiring and decide whether to expand the role.
Explain why you make recurring decisions, not just which steps to follow. That context lets your assistant handle exceptions without checking with you.
How to Retain a Great Executive Assistant
Keeping a strong assistant comes down to partnership. Give feedback in the moment, both positive and constructive, rather than saving it for quarterly reviews.
Recognize their contribution in front of your team, investors and partners. Check market pay regularly too, because a great assistant will hear from recruiters if your compensation falls behind.
Frequently Asked Questions
Where can I hire an executive assistant?
You can hire through job boards such as LinkedIn and Indeed, freelance marketplaces such as Upwork, managed assistant services or placement agencies that help you make a direct hire.
What's the difference between a virtual assistant and an executive assistant?
A virtual assistant usually handles defined tasks like data entry, while an executive assistant manages priorities, relationships and decisions on your behalf.
How many hours of support do I need?
Track your admin time for one typical week, total the work you could delegate and add a buffer for coordination and training.
Should I share my passwords with an executive assistant?
No. Use delegated access and individual accounts with multifactor authentication so permissions can be tracked and revoked.
Find the Support That Fits Your Stage
The right executive assistant gives you more than spare hours. They protect your focus, represent you well and keep the business moving when your calendar can't.
Start by defining what you need, then choose the hiring route that fits your budget and how much management you want to take on. With a clear role, a realistic interview process and a structured first 90 days, you'll be well placed to find someone who makes a lasting difference.
