EA / Book Keeper

About the role
I’m an executive running ann entertainment/talent supply business — and I’m looking for a sharp, reliable Executive Assistant who can also handle bookkeeping. This is a true right-hand role. I move fast across a lot of projects, and I need someone who can keep everything on track without me having to chase it.
If you’re organized to the point of being slightly obsessive, you like systems, and you take genuine ownership of your work, we’ll get along well.
What you’ll do
• Keep projects and tasks on track — manage and maintain task lists, project boards, and deadlines across both businesses so nothing slips
• Run point in Airtable — update records, maintain pipelines, keep data clean and accurate, and help me get the most out of our systems
• Bookkeeping — record transactions, reconcile accounts, track income and expenses, organize receipts/invoices, and keep the books current and tidy
• Inbox and calendar support — help triage email, schedule, and follow up so things don’t fall through the cracks
• General EA support — research, document prep, follow-ups, and the dozens of small things that keep a busy founder moving
• Flag and follow up proactively — tell me what needs my attention, chase what’s outstanding, and close loops without being reminded
What I’m looking for
• Trustworthy — you’ll have access to sensitive information and financials; integrity is non-negotiable
• Independent and driven — you can take a goal, run with it, and figure things out without hand-holding
• Highly organized — you naturally keep track of moving pieces and never lose the thread
• Strong written English — clear, professional communication
• Detail-oriented — accuracy matters a lot, especially with the books
Required experience
• Experience as an EA / VA supporting a founder or executive managing multiple projects
• Bookkeeping experience (we currently operate QuickBooks and have recently started an IRA option for the team)
• Comfortable with task/project management
Nice to have (a big plus)
• Airtable experience — this is the system that runs my businesses, so familiarity here moves you to the top of the pile
• Experience with shared inboxes (Missive), automation tools (Make), or AI tools
• Experience in entertainment, hospitality/cruise, or travel
The arrangement
We’ll start with a 3-month paid trial so we can both make sure it’s a great fit. If the trial goes well — and I expect it to with the right person — this becomes a permanent, long-term full-time role with room to grow as my businesses do. I want to find someone I can build with for years, not just fill a seat.
How to apply
Please don’t send a generic application. To show me you read this carefully:
1. Start your message with the word “Anchor” so I know you read to the end.
2. Tell me briefly about a founder or executive you’ve supported, and one thing you did that made their life easier.
3. List the bookkeeping tool(s) you’ve used and your level of Airtable experience (none / some / strong).
4. Attach/supply your resume if you have one.
Applications that follow these steps get read first. I’m looking forward to meeting you.