AI-Native Executive VA for a Multi-Business Founder (Night Shift)

Please read this whole post before applying. The last section tells you exactly how to apply, and I do check for it.

I don't run one business. I run several at once — a brand launch and operations company that has put out 50+ direct-to-consumer brands, a manufacturing and logistics business serving consumer brands, a media company I operate alongside its founder, and a handful of smaller ventures and acquisitions in progress. They all need attention on the same day.

That is the actual job. I need one person who can hold context across all of it — not a specialist in one lane, but someone who can go from a product launch for a consumer brand in the morning, to a deck for the media business in the afternoon, to chasing a supplier for the logistics company, and keep every thread straight.

In one week you might build a Canva carousel for a brand launch, answer twenty customer emails in one company's voice, clean a messy order export and tell me what it means, chase a supplier who has gone quiet, put together a tracker for an entirely different business, and then rebuild the system we use to run all of it. If that variety sounds exhausting, this isn't the job for you. If it sounds like the best part, keep reading.

THE HOURS — let's be honest about them up front.
This role works US Pacific business hours: 7:00 AM – 5:00 PM PT, which is 10:00 PM – 8:00 AM Manila time, Monday to Friday. It is a night shift. That is exactly why the pay is well above the market rate for this kind of role. If you can't sustain a night schedule long term, please don't apply — I'd genuinely rather you tell me now than three months in.

WHAT YOU'LL OWN
- Design execution — social posts, email headers, simple landing sections, product graphics, the occasional deck. Canva or Figma, working from existing brand templates. This is execution work, not brand identity design.
- Customer support — answering customer email and DMs in the right brand's voice, handling refunds, returns and shipping issues, escalating only what genuinely needs me.
- Data and light tech — order exports, Shopify and ad platform reports, Google Sheets, Zapier or Make automations, and building small tools with AI when the tool you need doesn't exist yet.
- Operations and organization — running trackers across several businesses, chasing suppliers, partners and freelancers, keeping projects moving without me having to ask twice.
- Being the responsive one — during your shift, messages get acknowledged within 30 minutes. Not always a full answer, but always an acknowledgement.

WHAT I'M LOOKING FOR
- You already use AI tools every single day — ChatGPT, Claude, Gemini or similar — and you can show me specifically how. This is the most important item on this list.
- You can hold several unrelated things in your head at once without dropping any of them. You'll be switching between businesses constantly, and each one has its own voice, customers and tools. If you need a single project at a time to do good work, you will be miserable here.
- Excellent written English. You will be writing to US customers and partners on behalf of these companies.
- You can make something look good in Canva without being told exactly what to make.
- Comfortable in Google Sheets — formulas, pivots, cleaning up messy data.
- You've worked with a US client or on a US schedule before, and it went well.
- Reliable internet plus a backup connection. A night shift with no power or internet contingency doesn't work.
- You solve first and ask second. When something breaks at 3 AM your time, I'm asleep. I need someone who makes a sensible call and tells me about it in the morning.

NICE TO HAVE
Shopify, Klaviyo, Meta Ads Manager, Zapier or Make, basic video editing, prior e-commerce or agency experience.

WHAT I OFFER
- $1,200 – $1,500 USD per month depending on experience, paid twice monthly via Wise.
- Full time, long term, working directly with me — no agency in between.
- Paid Philippine holidays, 10 days paid leave after 3 months, and a 13th month bonus.
- A paid AI tool budget, because I want you using the best tools available.
- A rare vantage point. You'll see the inside of several businesses at once — how they're launched, run and grown — which is not something most assistant roles offer.
- Real growth. The first person I hire here becomes the person who helps me hire the next one.

HOW THE HIRING WORKS
A short written application, then a 90-second screen recording of you building two things at once with AI, then a video call, then a paid two-week trial. To be clear about the recording: it takes two minutes, it is not meant to be perfect, and I'm watching how you move rather than what you produce. Messy and fast beats polished and slow.

HOW TO APPLY
Reply with the subject line "Night Owl — [your first name]" and answer these three things in your message:

1. Describe one specific task you do with an AI tool, and paste the actual prompt you use for it.
2. Tell me your real experience with a night schedule. Have you worked one? For how long? How did you handle it?
3. Link one thing you designed. Anything — a social post, a deck, a flyer.

Applications without that subject line get skipped, and so do applications that are clearly a generic template. Take fifteen minutes on this and you will stand out enormously.