How to Hire an Executive Assistant (2026 Guide)

Hiring an executive assistant is one of the most leverage-creating decisions one can make — or one of the most expensive mistakes.

This guide walks through how to hire an executive assistant in 2025, including:

When you actually need one
What executive assistants really do
The different types of EAs available today
Costs, trade-offs, and hiring mistakes
And how many leaders now approach this decision differently in an AI-native world

What Does an Executive Assistant Actually Do?

At a high level, an executive assistant exists to multiply the effectiveness of an executive.

In practice, this usually means owning three categories of work:

1. Time & Calendar Management

Scheduling meetings
Protecting focus time
Prioritising requests
Rescheduling and follow-ups

2. Communication & Coordination

Inbox management
Meeting preparation
Stakeholder coordination
Following up on action items

3. Operational Support

Travel planning
Document preparation
Light project management
Ad hoc problem solving

When Should You Hire an Executive Assistant?

There’s no single revenue or headcount threshold. Instead, look for these signals:

You delay meetings because scheduling feels painful
You spend evenings following up on logistics
You’re the bottleneck for coordination
Context switching is hurting focus and decision quality

If this feels familiar, you likely need EA support— whether through a person, a system, or both.

Types of Executive Assistants You Can Hire

In 2025, “executive assistant” no longer means one thing. There are several models, each with pros and cons.

1. Full-Time In-House Executive Assistant

Best for: Senior executives with complex, high-touch needs.

Pros

Deep context and trust
High ownership
Can anticipate needs over time

Cons

High fixed cost
Recruitment and onboarding time
Ongoing management required

This is the classic model — and still the right one in some cases.

2. Virtual or Fractional Executive Assistant

Best for: Founders who need flexibility.

Pros

Faster to start
Lower commitment
Access to experienced EAs

Cons

Shared attention
Less deep context
Boundaries around scope

Many founders try this first, especially during early growth.

3. AI Executive Assistants (The New Category)

AI executive assistants specialise in:

Scheduling and coordination
Calendar protection
Multi-party negotiation
Follow-ups and confirmations

An AI executive assistant like Carrie can be CC’d on email threads and handle scheduling end-to-end, without recruitment, onboarding, or ramp-up.

This model is increasingly used as a first step before hiring a human EA.

Executive Assistant Cost Breakdown

Cost is often the deciding factor when people search “hire an executive assistant”.

Full-Time EA Costs

Salary: $70k–$150k+
Benefits, taxes, overhead: +20–40%
Recruiter fees: up to 30% of salary

Real annual cost: often $120k–$180k+

Virtual & Agency EA Costs

$30–$70/hour
$2k–$6k+ monthly retainers

Lower commitment — but often less leverage.

AI Executive Assistant Costs

Subscription-based
No hiring or onboarding costs
Get started right away

Common Mistakes When Hiring an Executive Assistant

1. Hiring Too Early — or Too Late

Hiring too early wastes money. Hiring too late burns you out.

The right moment is when coordination becomes a bottleneck, not when you feel “busy.”

2. Hiring for Personality Instead of Workflow

Great EAs are not just personable — they’re operationally excellent.

Calendar logic, prioritisation, follow-ups, and systems matter more than charm.

3. Expecting Instant Leverage

Even the best human EAs need time to learn context.

There is always a ramp-up period.

A Smarter Way To Hire in 2025

An increasing number of people now follow a different sequence:

Start with an AI executive assistant to handle scheduling and coordination
Remove the operational drag immediately
Observe what higher-level work still needs human judgment
Hire a human EA later — if needed

This approach:

Reduces hiring risk
Delays six-figure commitments
Gives instant relief
Clarifies what role you actually need

AI handles the repeatable coordination; humans focus on nuance and judgment.

Final Thoughts: What “Hiring an Executive Assistant” Really Means

When people say they want to hire an executive assistant, they’re rarely asking for headcount.

They’re asking for:

Fewer decisions
Fewer interruptions
Fewer logistical headaches

In 2025, that doesn’t always require hiring a person first.

If you’re exploring whether you need to hire an executive assistant, the lowest-risk place to start is to remove the operational friction first.

Try Carrie and experience what it feels like to have scheduling and coordination handled for you — in under a minute.

👉 Get started with Carrie