The short version
I'm looking for one person to own the operational layer of my life and my businesses. Not a task-taker. Someone who takes a messy voice note, comes back with a plan, and then closes it out without me having to ask twice.
This is a long-term role.
What you'd actually be doing
Personal & family
Immigration and documents across several jurisdictions — visas, passports, residency renewals, attestations, notary
Medical — booking specialists, chasing referrals and reports, keeping records organised across countries
Households — leases, utilities, insurance, contractors
Pets that travel internationally — vets, health certificates, relocation logistics
Family logistics
Travel
Flights, hotels, transfers, restaurants — frequently, and often at short notice
Full itineraries with contacts, addresses, map links and confirmation numbers in one document
Business
Inbox triage on multiple mailboxes — surface what matters, summarise it, kill the noise
Invoices and receipts collected, filed, and packaged quarterly for my accountant
Vendor sourcing — get quotes, compare, recommend, negotiate, book
Research — markets, suppliers, agencies, service providers — delivered as a short brief with a recommendation, not a wall of links
Contract admin, e-signature routing, corporate filings coordination
System building
Every recurring task becomes a documented SOP
Every deadline lives in a register with alerts set well in advance
When it's quiet, you're building the system that makes the busy weeks survivable
Who this is for
Non-negotiable
Direct experience supporting a CEO, founder or C-level executive. Not a call centre, not general admin, not a VA agency queue. You've been someone's right hand and you can name them.
Fluent English and Spanish, written and spoken. You'll be drafting emails in my voice and calling Spanish-speaking clinics, government offices and vendors in the same day. Written English is tested — a lot of this job is writing.
You live in Argentina, Uruguay, Chile, Paraguay or Venezuela, or elsewhere in South America with a genuine willingness to start your day at 07:00–09:00 local. I work across UTC+2 to UTC+4. Your morning is my afternoon — that overlap is the whole point.
AI-literate, with judgment. You use Claude or ChatGPT daily to draft, research, summarise and structure. You also know when the model is wrong, when it's guessing, and when a phone call gets the answer faster. I don't want AI output pasted at me. I want your thinking, accelerated by AI.
Comfortable on the phone. A significant part of this job is calling people who haven't replied to email.
Contactable references from the executives you supported, who I will call.
What actually makes someone good at this
You chase. If someone said "Monday", you have a reminder set for Monday morning and you follow up Monday morning.
You escalate fast and unprompted. If something has gone wrong, I hear it from you within the hour — not from an email I stumble across three days later.
You come with options and a recommendation, not an open question.
You anticipate the next blocker and ask about it in the same call, so we're not chasing the same vendor four times.
You keep the system current without being told. Tasks have status, notes, subtasks and dates — not a link and a shrug.
You say "I don't know yet, here's what I'm doing to find out" rather than going quiet.
Honest notes about this role
The workload is uneven. Some weeks are 90 minutes a day. Others are relentless — a property purchase, an international move and a family medical situation at once. You're paid a flat retainer for the quiet weeks and overtime for the heavy ones. If unpredictability stresses you, this isn't the right fit.
I give direct feedback, quickly. If something isn't working I'll say so plainly and expect it fixed. Equally, I'll tell you when something's been done well, and I back my people.
I need reliability more than brilliance. Life happens and I'm reasonable about it — but I need to know early, and I need a handover so nothing stalls. The single fastest way to lose this role is to go quiet.
Discretion is absolute. You'll see medical records, bank details, contracts and family matters. NDA on day one.
Terms
Salary — USD 1,000–1,400 per month depending on experience, paid in USD
Hours — approximately 20 per week (around 4 a day, Monday to Friday), core overlap 07:00–11:00 your time
Overtime — paid hourly above 90 hours a month, agreed in advance
Contract — independent contractor, 3-month probation, reviewed at 6 and 12 months
Time off — 20 days paid annual leave plus local public holidays, planned in advance
Equipment — must have good working laptop - responsible for own hardware - and paid AI and software subscriptions provided
Growth — scope and hours can grow. I'd like this to become a full-time chief-of-staff role over time for the right person.
Tools: ClickUp, Google Workspace, Claude, Loom, WhatsApp Business, Wise, 1Password. You don't need to know all of these on day one, but you need to be the kind of person who learns a tool properly rather than using 10% of it.
How to apply
Please don't send a generic CV and cover letter — I won't read it. Send the following to jack@cheshire.co with the subject line "PA — [your name] — [your city]":
Your CV, plus the name, title and company of the executive or executives you directly supported.
A 3-minute Loom or video, camera on, in English, covering: who you supported, for how long, and what you owned end to end; the single most complex thing you organised for them; your current time zone and what time you'd start.
Three short written answers, maximum 150 words each:
Tell me about a time you had to tell your boss something had gone wrong or been missed. What did you say, and how quickly?
Describe a task where you deliberately did not use AI, and why.
It's a slow week. Nothing urgent is in the queue. What do you do?
Strong candidates will be invited to a paid trial task (2–3 hours, paid at your quoted rate) before any interview. I check references with the executive directly, not with HR.
I read every application that follows the format above. If you don't hear from me within two weeks, assume it's a no — and thank you for the time.
