ALL ROLES / EXECUTIVE ASSISTANTS

Hire an executive assistant who protects your calendar and your focus

Outsourced executive support is usually sold as a pool of hours shared across clients. This is one person, dedicated to you, working your hours from Latin America, and you decide what they own.

Book a meeting
Clutch: 5.0/5
Trustpilot: 4.6/5
G2: 4.9/5
Assistants coordinating schedules and calls from their laptops

TRUSTED BY TEAMS WHOSE CLOUDTASK HIRES HAVE STAYED 5 TO 8 YEARS

  • Apollo
  • Vonage
  • Expensify
  • GetAccept

How it works

How do I hire an executive assistant?

You do one thing: interview. We handle everything else.

1

Post the role

5 minutes. The role, the motion, the tools, the comp band. That is all we need to start.

2

Review your matches

3 to 5 matches in 48 hours.

3

Interview and hire

We coordinate interviews. On Managed Staffing, we also handle payroll and compliance across LATAM.

How it works

WHY TEAMS TRUST CLOUDTASK

What you get with every hire

Your hours, not a shared pool

One person, dedicated, working your working day from Latin America. Not a block of hours split across five other clients.

Screened for judgment

The skill that matters is knowing what to escalate and what to absorb. We screen for it in a live call, because a resume cannot show it.

Verified on your stack

Google Workspace, Outlook, Slack, Notion, HubSpot, Salesforce. Tools are checked per candidate instead of taken from a self-reported list.

Replacement guarantee

24 months on Managed Staffing, 6 months on Direct Hire. Executive support is a trust hire, and the guarantee is there for the case where the fit is wrong.

WHY CLOUDTASK

Staffing with numbers behind it

10,000+

hires placed

since 2016

85%

still in seat

past 90 days

24 months

replacement guarantee

on Managed Staffing

12

countries

across Latin America and the Caribbean

PRICING MODEL

Managed Staffing.

Managed Staffing is open to every role we place. We find the person, handle payments and compliance, and stay involved after the hire with check-ins, visibility, and escalation when something is off. You get the person. We keep the machine running. For roles that create demand, outbound SDRs, BDRs, demand generation and full-cycle AEs, Managed Staffing runs on a six-month minimum term.

Pay

One all-in monthly rate

Per person. That is the number, and there is nothing added to it.

In the monthly rate

  • Sourcing from the CloudTask staffing and recruiting company
  • Screening and vetting
  • Matching coordination
  • Worker payments
  • Compliance and employment administration
  • Onboarding support at day 0, 7, 30 and 60
  • Ongoing check-ins with the hire and with you
  • Time and activity tracking, on by default
  • Performance escalation
  • 24-month replacement guarantee. Replacements not capped.
  • Health benefits available on request
  • Equipment benefits available on request

Stays with you

  • The work itself
  • Priorities and direction
  • Who you hire

$299 to start your search. One time, not a subscription. It applies to your buyout or toward your first placement.

Start your search

PRICING MODEL

Direct Hire.

Direct Hire is open to every role we place. We find the person, vet them, and hand them over. You employ them, you manage them, you own the relationship from day one. Roles that create demand usually land here, because live call feedback and daily coaching work best coming straight from your sales leader, and there is no minimum term.

Pay

20% to 30%

Of first-year base salary. One time, quoted per role, paid when they accept.

In the fee

  • Sourcing from the CloudTask staffing and recruiting company
  • Screening and vetting
  • Shortlist of matched candidates
  • Interview coordination
  • Offer support
  • 6-month replacement guarantee. One replacement, same job description.

Yours when they accept

  • Employment and payroll
  • Compliance and employment administration
  • Ongoing management
  • Time and activity tracking
  • Health benefits and equipment benefits

$299 to start your search. One time, not a subscription. It applies to your buyout or toward your first placement.

Start your search

How CloudTask compares

Run the numbers. We did.

The same role, three ways to fill it.

Swipe to compare

US Direct Hire Staffing Agency
Time to First Interview 48 hours 3 to 6 weeks 2 to 4 weeks
Payroll & Compliance Included on Managed Staffing You manage Included in rate
Vetting Process Human + AI verified You screen Recruiter screened
Candidate spam Screened out before you see a profile Common Low
Tool Verification Verified per candidate Self-reported Rarely verified
Free Replacements 24 months on Managed Staffing, 6 months on Direct Hire None Variable
See all comparison

Testimonials

Trusted by teams that hire with us

  • LATAM has been a gold mine for talent. Our CloudTask hires understand our company culture and mission, and they connect with our customers in a way that drives high NPS and CX scores.
    David Barrett
    David Barrett CEO, Expensify
  • At first we were an SF-based team only. Then I met Amir Reiter back in 2018. After visiting Medellín, I knew LATAM would be key to our growth and success.
    Tim Zheng
    Tim Zheng CEO, Apollo.io
  • After meeting my CX and CS team in Medellín, we immediately loved the culture and the work ethic. As a European-HQ company, we found LATAM to be perfect to service our American clients.
    Carl Carell
    Carl Carell CRO and Co-founder, GetAccept

SKILLS

Top capabilities to look for in an executive assistant

Calendar management is the visible part and the easiest to teach. These are the capabilities that decide whether the hire buys you time or costs you time.

  • Calendar as a priority instrument

    Not just booking what comes in. Protecting deep work, batching the noise, and saying no on your behalf without burning a relationship.

  • Inbox triage and drafting

    Sorting what needs you from what needs a reply, and drafting the reply in your voice so you are approving rather than composing.

  • Judgment on escalation

    Knowing the difference between something to handle, something to flag, and something to interrupt you for. This is the capability that separates a great assistant from an expensive one.

  • Discretion by default

    Board material, comp conversations, legal threads. Treating everything as restricted and never improvising when a request falls outside the process.

  • Travel and logistics under pressure

    Building an itinerary that survives a canceled flight, and rebuilding it at 6am without waking you to ask what to do.

  • Meeting prep and follow through

    The brief before, the notes during, the actions after, and the chase until they are closed. Most of the value of a meeting is created outside it.

  • Owning a recurring process

    Board packs, expense cycles, reporting, onboarding. A strong assistant takes a process off you permanently rather than helping with it each time.

  • AI where it saves a step

    Drafting, summarizing and research. Useful for the first version of something, and never for the judgment call about whether to send it.

HIRING GUIDE

How to hire an executive assistant

Executive support is the role people hire last and regret waiting on. It is also the role where outsourcing and hiring look identical from the outside and behave completely differently. This guide covers the difference, what to screen for, and when you should not hire one at all.

What does an executive assistant actually do?

The job is not tasks, it is attention. An executive assistant decides what reaches you, in what order, and with what context attached, so that the hours you spend are spent on the things only you can do.

In practice that means the calendar, the inbox, meeting preparation and follow through, travel, and one or two recurring processes owned end to end. The list varies. The principle does not: anything that can be decided without you should be.

How is a dedicated assistant different from an outsourced EA service?

Most outsourced executive support is a pool. You buy a block of hours, the provider assigns whoever is free, and the person handling your calendar this month may not be the one handling it next month. It is cheap because it is shared.

A dedicated hire is one person who learns your business, your people and your preferences, and keeps that knowledge. The cost of executive support is almost entirely the cost of context, and a pool resets that context constantly.

When should you not hire an executive assistant?

When you cannot yet name what you would hand over. The most common failure is hiring one and then spending six weeks failing to delegate, which reads as a bad hire and is actually an undefined role.

It is also the wrong hire when what you need is an operations person or a project manager. If the work is running a process across a team rather than protecting one person's time, hire for that instead.

And if you genuinely need five hours a month, a pooled service is the right purchase. Hire a dedicated assistant when the work is continuous and the context compounds.

What should I screen for in the interview?

Give a real scenario with a conflict in it: two things booked over each other, one of them with a customer, and no clean answer. What you are testing is whether they ask the right question or invent a resolution.

Then ask what they stopped doing in their last role and why. A strong assistant prunes. Someone who has only ever added tasks will add them to your life too.

Red flags in executive assistant candidates

Inventing the resolution. In the conflict scenario, a candidate who picks a winner without asking which meeting matters more, or who the customer is, will make that call for you on a real day. You want a question before you get an answer.

Nothing ever stopped. Ask what they stopped doing in their last role. A candidate who cannot name anything, or who describes the job as a list that kept growing, will fill your week rather than clear it.

Escalating everything, or nothing. Ask for one thing they handled without telling their executive and one thing they interrupted them for. Someone who flags everything is handing the work back to you, and someone who flags nothing is making calls that were never theirs.

Loose talk about past executives. A candidate who shares details of a previous executive's board material, pay conversations or private matters to make a story more interesting will treat yours the same way.

A calendar that only accepts. If they describe calendar work as fitting in whatever gets requested, they have booked meetings but never protected anyone's focus. Ask how they decided what not to book.

How much executive support do I actually need?

Look at one week of your calendar and mark every block that exists because of coordination rather than judgment. That number is the honest starting point, and for most founders and executives it is larger than expected.

Start with a defined scope rather than a vague one. Calendar and inbox in month one, meeting prep and travel in month two, one owned process by month three. Handing over everything on day one is how the role fails.

How much does an executive assistant cost?

It depends on seniority, on the language requirement, and on the country the person works from, and any page that gives you a single number is describing one scenario and calling it a price.

What is worth understanding is the shape. On Managed Staffing it is one all-in monthly rate per person with payments, compliance and replacement cover inside it. On Direct Hire it is a one-time fee and the person goes on your payroll. We quote your number before you interview anyone.

Why hire an executive assistant in Latin America?

Overlap. Executive support is a real time role: the value of someone who can reach you, reach your team and reach a customer inside the same working day is most of the value. Latin America and the Caribbean cover the full US day.

The second reason is that this is a spoken and written role in English, all day, with your customers and your board. That is the constraint we screen live rather than infer from a profile.

What goes wrong in the first 90 days?

Three things, in order of frequency. The scope was never written down, so both sides guess. Access was never granted, so the assistant is asking permission instead of working. And nobody scheduled a weekly review, so small misreads compound into a bad fit narrative.

All three are fixed before the first week. Write the scope, grant the access on day one, and hold a 20-minute review every Friday for the first month.

How does CloudTask hire for this role?

You send the scope, the tools and the hours you need covered. We come back with 3 to 5 matched profiles within 48 hours, each one screened on a live call and verified against the stack you named.

You interview and choose. On Managed Staffing we handle payments, compliance and onboarding and stay in the loop with check-ins. On Direct Hire the person joins your payroll from day one. Both carry a replacement guarantee: 24 months on Managed Staffing, 6 months on Direct Hire.

FAQ

The fine print, in plain terms.

What does a virtual executive assistant do?
The same work as an in-house executive assistant, done remotely: calendar, inbox, meeting preparation and follow through, travel, and any recurring process you hand over. The difference is location, not scope.
How much does a virtual executive assistant cost?
It depends on seniority, language requirement and country, so a single published number would be misleading. What we can tell you is the structure: one all-in monthly rate per person on Managed Staffing, or a one-time fee on Direct Hire. We quote your role before you interview.
Is this a dedicated assistant or a shared pool of hours?
Dedicated. One person, working your hours, who learns your business and keeps that context. Pooled hours are a different product and a cheaper one, and they are the better choice if you genuinely need only a few hours a month.
How fast can someone start?
You get 3 to 5 matched profiles within 48 hours. After you choose, plan for the first two weeks to go on scope, access and shadowing rather than output.
Can they work in our tools and email domain?
Yes. The person works inside your Workspace or Microsoft tenant, your calendar and your CRM, under whatever access policy you set.
What is the $299 for?
It starts your search. One time, not a subscription. It applies to your first placement or toward a buyout, so it is not an extra cost, it is the first part of one.
Why is there no number on the monthly rate?
Because it depends on the role, the seniority and the country. We quote the all-in monthly rate per person before you interview, so you know the number before you commit to anyone.
Who is the legal employer?
On Managed Staffing, CloudTask is the contracting party and handles payments and compliance, and you direct the work. On Direct Hire, you employ and manage the hire from day one.
How does tracking work, and can I turn it off?
On Managed Staffing, time and activity tracking is on by default. Talk to us about your setup when you start your search.
What happens if the person does not work out?
Managed Staffing carries a 24-month replacement guarantee, and replacements are not capped. Direct Hire carries a 6-month replacement guarantee: one replacement for the same job description.
Is there a platform or subscription fee?
No. $299 starts your search, one time, and applies toward your first placement. There is no subscription.

Ready to hire?

3 to 5 matches in 48 hours. Start with a quick role brief to get your shortlist.

Get matched