Bilingual (Spanish/English) Executive Assistant, Costa Rica-Based, Remote & Flexible

I'm an entrepreneur running several businesses at once, and I'm looking for a sharp, reliable executive assistant based in Costa Rica to become my right hand. You'd help me stay on top of the day-to-day across everything I run: a growing software product, a wholesale and retail bakery here in Costa Rica, independent software consulting for a handful of clients, and general personal and household admin. Being based in Costa Rica puts you in a great time zone for both the local bakery and my U.S.-facing work. This starts as flexible, as-needed work (hourly, no fixed schedule) so we can find a rhythm and build trust. For the right person it grows into a steady, long-term role with more hours and more responsibility. I automate a lot of my work with AI tools, so I move fast and value someone who can keep up and take things off my plate without a lot of hand-holding. WHAT YOU'LL HELP ME WITH (it varies week to week) The software product - Answer and triage customer support messages and help users get unstuck - Keep help docs, FAQs, and saved replies up to date - Light research (competitors, users, outreach lists) and organizing feedback for my dev team - Schedule and post community and social updates The bakery (in Spanish) - Coordinate orders, suppliers, and staff communication in Spanish - Schedule and post social media content (Facebook and Instagram) - Enter sales and inventory data in our point-of-sale system and keep simple records - Handle customer inquiries and follow-ups, plus occasional local coordination Consulting and client work - Manage my calendar and schedule meetings across time zones - Prepare invoices and handle light bookkeeping admin - Take meeting notes and track follow-ups - Format documents and tidy up deliverables Personal and general - Keep my inbox and calendar under control - Book travel, set appointments, and send reminders - Run online research and errands - Keep my projects and to-do lists organized across all of the above WHO I'M LOOKING FOR - Based in Costa Rica (required) - Fully bilingual in English and Spanish, with professional-level writing in both - Real experience as an executive or virtual assistant, ideally supporting a busy entrepreneur or more than one business - Genuinely organized, proactive, and detail-oriented; you catch things before I do - Comfortable with everyday tools (Google Workspace, spreadsheets, Notion) and quick to learn new ones - Comfortable using AI tools like ChatGPT or Claude to work faster, or eager to learn - Discreet and trustworthy with confidential business and personal information (customer data, financials, payroll, personal details) - Reliable internet, responsive and communicative, and able to work independently NICE TO HAVE - Social media and content-scheduling experience - Basic bookkeeping or point-of-sale experience - Customer support experience for a software or tech product - Experience with a small food, retail, or e-commerce business HOW WE'LL WORK Remote, flexible hours to start, paid hourly. I'd like to begin with a few small paid tasks so we can both see if it's a good fit, then grow from there. I'm looking for a long-term relationship, not a one-off. TO APPLY 1. Start your reply with the words "Pura Vida" so I know you actually read this. 2. Confirm you're based in Costa Rica and fully bilingual in English and Spanish. 3. In two or three sentences, tell me about your relevant EA or VA experience (bonus points for juggling more than one business at a time). 4. List the tools you're strongest with. Looking forward to meeting my next right hand.