How to Hire an Executive Assistant
A hiring guide for founders and executives handing their inbox, calendar, and travel to someone they may never meet in person. What EAs cost in the US and offshore, a job description to copy, interview questions that test judgment, and a screening process that lets you hear the person before you hand over the passwords.
Benefits of Hiring an Executive Assistant
A good executive assistant returns ten hours a week and takes decisions off your desk that never needed you. A bad one costs you a board deadline.
Ten hours a week back
Scheduling, inbox triage, expense reports, and travel changes eat 10 to 15 hours of an executive's week. An EA takes all of it, plus most of the follow-up.
A gatekeeper for your attention
Meeting requests get declined, shortened, or pushed to email before they reach you. You see the three things that matter today instead of the forty that arrived.
Nothing slips after a meeting
Action items get logged, owners get chased, and the follow-up email goes out that afternoon. Investors and clients notice the difference within a month.
Travel handled end to end
Flights rebooked during a delay, visas checked, a hotel near the client's office. You land and walk in.
Board and leadership prep runs on rails
Decks collected a week out, agendas circulated, minutes done the same day. Quarterly prep stops being a scramble.
Continuity when you are unreachable
On a flight or in a two-day offsite, someone with context is still answering, rescheduling, and flagging what cannot wait.
How to Hire an Executive Assistant: Step by Step
Three to four weeks from posting to a working EA. Every step exists because this person will read your email and speak in your name.
- 1
Write down what you will hand over
Day 1List a real week: which meetings they will schedule, whether they will answer email as you, what they will book and expense. The list decides whether you need a senior EA at $90K or a strong remote assistant at $25 an hour.
- 2
Decide US-based or offshore
Day 1–2US-based if the role sits in leadership meetings or handles board members. Offshore (Philippines, Latin America) if the work is scheduling, inbox, and travel and you can define the hours. Plenty of executives run one of each.
- 3
Post with the hours and the access spelled out
Day 2Use the template below. State the time zone, whether they will send email as you, and that shortlisted applicants record short video answers. Vague postings pull 300 generic applications; specific ones pull 150 relevant ones.
- 4
Screen with three video questions
Week 1How they ran their last executive's calendar, what they do with a conflict when the boss is unreachable, and a two-minute introduction so you can hear their English and composure. Watch at 1.5x and cut 150 to 20 in an evening.
- 5
Run a paid inbox and calendar exercise
Week 2Give the top 8 a mock inbox with 25 emails and a week of conflicting requests. Forty-five minutes. Who triaged well, who wrote replies you would actually send, who asked the right clarifying question.
- 6
Interview, reference, trial
Week 3–4Two conversations on judgment and discretion, one reference call with the last executive they supported, then a paid two-week trial with calendar-only access. Expand access as trust builds.
Cost of Hiring an Executive Assistant
EA pay tracks the seniority of the executive and the market. A remote assistant handling scheduling and an EA supporting a public-company CEO are different hires with a 5x price gap.
| Cost component | Typical range | Notes |
|---|---|---|
| US-based full-time EA | $50K – $100K /yr | Top of the range for C-suite support in major metros, plus benefits |
| Senior EA / chief of staff hybrid | $100K – $140K /yr | Runs projects and the leadership rhythm as well as the calendar |
| Offshore EA (Philippines, LatAm) | $8 – $20 /hr | Strong English and US-hours overlap at the top end |
| US freelance / fractional EA | $30 – $60 /hr | Part-time support for 10 to 20 hours a week |
| EA staffing agency | 20% – 30% of salary | One-time placement fee; managed remote EA services run $2,000 to $4,000 a month |
| Cost of a bad hire | Access + trust | A missed board deadline or a forwarded email you never wanted forwarded costs more than the salary |
Job Description for an Executive Assistant
A template you can post today. Say who they support, whether they send email in your name, and the hours, because those three things decide who applies.
About the Role We're hiring an Executive Assistant to support our [CEO / founder / VP of X]. You'll run the calendar, manage the inbox, handle travel and expenses, and keep the leadership team's weekly rhythm on track. This is a trusted role: you'll see sensitive information from day one and often speak on the executive's behalf. What You'll Do - Own the executive's calendar: schedule, protect focus time, resolve conflicts, and prep briefing notes for each meeting - Triage and respond to email in the executive's voice using agreed guidelines - Book and manage travel, including changes mid-trip - Prepare expense reports and track approvals - Coordinate board and leadership meetings: agendas, materials, minutes, follow-ups - Keep a running list of action items and chase owners until they're done What We're Looking For - 3+ years supporting a senior executive (founder, C-suite, or VP) - Excellent written English; you'll draft emails that go out under someone else's name - Calm and decisive when plans change and the executive is unreachable - Experience with [Google Workspace / Microsoft 365], [your CRM], and a password manager - Discretion: references will be asked about it directly - [X hours] of overlap with [time zone]; [remote / hybrid / on-site in city] Hours & Compensation - [Full-time], [salary range or hourly rate] - [Benefits, if applicable] - Long-term role with a path into operations or chief of staff work for the right person How to Apply Apply with a short note on the executive you supported longest and what you took off their plate. Shortlisted candidates will record short video answers (about 10 minutes, on your own time) so we can hear how you think through a scheduling conflict before we meet.
Questions to Ask an Executive Assistant
EA resumes list the same tools and the same adjectives. Ask for the specific week, the specific conflict, the specific save.
Walk me through how you ran your last executive's calendar. What were your rules?
Named rules: no meetings before 10, Friday afternoons blocked, a 15-minute buffer after external calls. Vague answers mean the calendar ran them.
Your executive is on a flight. The board chair wants 30 minutes today and the only slot is a customer call. What do you do?
They make the call, explain the reasoning, and brief the executive on landing. Freezing until the plane lands is the wrong answer.
Tell me about an email you drafted in your executive's voice that they sent without edits.
Specifics about tone and length, and how they learned the voice. Follow up with a live sample: a three-line decline to a vendor, written as you.
What information did you hold that nobody else in the company could see, and how did you handle it?
Comfort with the question and concrete habits: separate vaults, no forwarding, screen locked when they step away. Any hint of gossip is disqualifying.
Describe a trip you rebooked while the executive was already traveling.
A real story with the airline, the alternative, and how fast the executive knew. EAs who have done this tell it in order and without drama.
What did your first two weeks with your last executive look like?
A ramp they drove: access checklist, shadowing the inbox, a preferences document. Experienced EAs bring the playbook so you don't have to write it.
What to Look For in Executive Assistant Candidates
The portfolio for this role is how they communicate with you during the process. Every email, every scheduled call, every follow-up is a work sample.
Green flags
Replies that are short and complete
Their application emails answer the question, confirm the time, and stop. That is what your investors will receive.
Calm on video
On a recorded answer they pause, think, and speak clearly. EAs absorb pressure for a living, and you can see whether this one can.
They ask about access and boundaries
Questions about password managers, email delegation, and what they can decide alone show they have done this before.
Long tenures with named executives
Three years with one VP tells you more than eight roles in four years.
They mention systems unprompted
A preferences doc, a Friday review, a standing travel profile. Organized people cannot hide it.
Red flags
A template cover letter
For a role built on attention to detail, a generic application fails the test in the first line.
Names dropped, work vague
Plenty about the executives they supported, little about what they actually did on a Tuesday.
Every tool, every skill
Bookkeeping, marketing, design, and project management in one resume usually means shallow in each.
Rescheduled the interview twice
For most roles that is life. For an EA, scheduling is the job.
What Executive Assistants Look For in Companies
Good EAs are interviewing you too. They have supported executives who were a nightmare and have decided not to do it again.
An executive who communicates
A weekly 20-minute sync and a straight answer when they ask whether you want a meeting or not.
Authority to decide
Permission to decline meetings and rebook travel without a text thread for every change.
A defined scope
EA work, chief-of-staff projects, or personal errands. They want to know which before they start, and to be paid for the one they get.
Respect for their hours
Agreed overlap honored, and no expectation that an 11pm message gets an 11:05pm reply unless the role pays for on-call.
A path to more
Many EAs become operations managers or chiefs of staff. The ones who stay for years work for executives who offer that route.
Remote Hiring for Executive Assistants
Calendar, inbox, travel, and expenses are already remote work. The EA of a founder in Austin can sit in Manila or Bogota and run the day. The parts that still favor in-person are hosting board members, managing an office, and sitting in leadership meetings.
Decide overlap before you pick a market
Four hours of overlap covers most scheduling work. Full overlap (Latin America for US teams) covers same-day fire drills.
Delegated access replaces the desk outside your door
Google Workspace delegation, a shared password vault, and a corporate card with a limit give a remote EA everything an in-office one had.
Trust is built in tiers
Week one: calendar. Month one: inbox. Month three: sending as you and booking on the card. Expanding on a schedule beats deciding by gut.
Video screening does the meeting for you
You will not bump into this person in a hallway. Three recorded answers show you the composure, the English, and the judgment before any live call.
Screening Tools for Hiring an Executive Assistant
What teams use to get from 150 applicants to one EA. The common thread is seeing how they communicate before you trust them with yours.
LinkedIn / Indeed / OnlineJobs.ph
SourcingLinkedIn and Indeed for US-based EAs, OnlineJobs.ph and Upwork for Philippine and Latin American assistants. Expect 150+ applications within a week.
Mock inbox exercise
Skill signalTwenty-five emails and a week of conflicts, 45 minutes, paid. Shows triage, writing, and judgment in one sitting.
Writing sample
Voice checkA three-line decline to a vendor and a warm intro to a candidate, both written as you. Tests whether they can borrow your voice.
Reference call with the last executive
Trust signalTen minutes on reliability, discretion, and what happened when things went wrong.
Hirevire
Async video screeningEvery EA resume says organized, discreet, and proactive. Send applicants three video questions and within two minutes you can see which ones stay composed under a hard scenario and speak the way you would want your investors to hear. Applicants record on their own time, you review 150 answers in an evening, and nobody gets near your inbox until you have met them.
Try Hirevire freePaid two-week trial
Final roundReal calendar, limited access, daily check-in. The definitive test for your final two.
Frequently Asked Questions
Common questions about hiring an Executive Assistant.
Further Resources
Free Hirevire resources to go deeper on hiring an Executive Assistant.