Executive Assistant

We're hiring an Executive Assistant to work directly under our Senior EA, supporting day-to-day operations across a small portfolio of businesses. You'll be the execution layer — the person who keeps calendars tidy, books gets booked, expenses get logged, and recurring processes run on time. This is not a strategic or client-facing role. You will not be making judgment calls on behalf of the principal, drafting high-stakes communication, or owning ambiguous projects. You'll be the reliable hands behind a well-run operation, working from clear SOPs and templates the Senior EA will provide. If you love systems, take pride in things being done correctly and on time, and want to grow your EA career under an experienced mentor, this role is for you. What you'll do: 1. Daily and weekly execution Manage calendar events: create, update, and reschedule meetings; send invites; track RSVPs Book travel — flights, hotels, restaurant reservations — against established preferences Triage inboxes: sort, label, archive, and flag items requiring the Senior EA's attention Compile meeting prep documents (agendas, attendee context, prior notes) from templates Support podcast management, from guest bookings to go-live 2. Bookkeeping and finance support Enter expenses into FreeAgent and other accounting tools against pre-set categorization rules Generate invoices from templates on a monthly cycle Execute contractor payments once approved Receive and queue reimbursement requests for review Maintain property income and expense trackers 3. Recurring operations Coordinate podcast logistics: send guest invites from templates, schedule recordings, hand off files to editors, maintain the production tracker Maintain the personal events tracker (birthdays, anniversaries, holidays) and surface reminders 2–3 weeks ahead Book health appointments once providers are identified Assemble recurring reports (expense summaries, podcast metrics, property P&L) from templates What We're Looking For Must-haves 1–3 years of experience as an EA, virtual assistant, or admin coordinator Strong written English - clear, professional, error-free for routine correspondence Comfortable with Google Workspace (Calendar, Gmail, Docs, Sheets) at an intermediate level Willingness and ability to learn new tools quickly (FreeAgent, project management software, AI tools) Highly organized, detail-oriented, and follow-through-driven - you finish what you start Discreet and trustworthy - you'll have visibility into inboxes, calendars, and financial data Reliable internet, quiet workspace, and consistent daily availability during agreed hours Uses AI tools as a productivity multiplier, not a crutch - you draft with AI assistance where it helps, but you review, refine, and add the human judgment before anything goes out. We don't want copy-pasted ChatGPT slop, we want your work, made faster and sharper by AI.