Experienced Executive Assistant to Founder | Operations, Life Admin & Second-Brain Support

I'm looking for an experienced Executive Assistant who can become my second brain, not simply wait for instructions. I run a growing direct-to-consumer beauty business and need someone who can take ownership of personal and business admin, think ahead, organize moving parts, follow up independently, and reduce the number of small decisions I have to make every day. This is not a basic virtual assistant, data-entry, or reminder-only role. I need someone who has previously supported a founder, entrepreneur, executive, or busy business owner in a high-trust position and understands how to manage tasks from beginning to end without excessive hand-holding. My ideal assistant notices what is missing, identifies conflicts, recommends the next step, follows up without being reminded, and only brings me in when a decision or approval genuinely requires me. Non-Negotiables (please read carefully before applying) - Availability from 11:00 AM SAST (South Africa time) onward, Monday to Sunday with light weekend coverage. This is not standby time — it's a real working window where you can be reached, acknowledge tasks, and move things forward. - Acknowledgment within 30–60 minutes during your availability window, even if the answer is just "Received, I'll handle this by [time]." I need to know a task has been seen so I can mentally let it go. - Proactive updates without being asked. If something is completed, delayed, waiting on someone, or needs my decision — you tell me. I should never have to chase you for a status. - Day-before appointment reminders sent without being asked. A short "Tomorrow's schedule" message with time, location, and leave-by time. - You must own an iPhone or have an active Apple ID with access to the Apple Reminders app. My entire personal and business life runs through Apple Reminders. Shared reminder lists are how we will coordinate appointments and tasks. This is a hard requirement — please do not apply if you use only Android or Windows. - Hands-on Shopify experience is required. You should already know how to look up customer orders, find tracking, check order history, and investigate customer support cases without me explaining the platform. I need someone I can hand a customer issue to, not someone I have to teach Shopify to. Examples of what ownership looks like - A customer was promised a refund by our automated support bot, but the refund still needs to be processed. You notice and flag the required action. - A trip is cancelled, so you review and update any reminders, bookings, or purchases connected to that trip. - Two appointments overlap, so you identify the conflict before anything is booked. - A supplier has not responded, so you follow up and keep the task open until there is a clear resolution. - An appointment is at 2:30 PM, so you ensure the reminder arrives early enough for preparation or travel. - I send you an unclear voice note or screenshot, and you organize it into clear actions, identify missing information, and move it forward. Responsibilities - Own and maintain a clear action tracker for personal and business tasks - Manage appointments, reminders, bookings, confirmations, and rescheduling through Apple Reminders - Review schedules and identify conflicts or missing steps - Monitor customer support emails and identify cases needing human action - Investigate customer orders directly in Shopify (tracking, addresses, order history, delivery status) - Draft customer replies and summarize issues requiring approval - Coordinate directly with suppliers and logistics partners - Follow up on shipping delays, address changes, refunds, reshipments, and tracking issues - Research services, products, laboratories, accommodation, travel, and other options - Provide a small number of well-researched recommendations rather than long lists - Plan travel, including Airbnb/hotel research, flights, transfers, and local logistics - Coordinate clinics, dentists, salons, barbers, cleaners, deliveries, and personal appointments - Assist with grocery or regular purchasing coordination - Manage inbox follow-ups and unresolved tasks - Create simple systems or SOPs when recurring work can be streamlined - Send concise updates showing what is complete, pending, waiting on someone, or needs my decision - Think one or two steps ahead instead of waiting for every instruction What I'm Looking For - At least 1–3 years of direct Executive Assistant experience - Proven experience supporting a founder, entrepreneur, or executive - Hands-on working experience with Shopify (customer orders, tracking, support cases) - Owns an iPhone or has active Apple ID with Apple Reminders access - Excellent written and spoken English - Strong judgment and problem-solving ability - Proactive rather than reactive - Able to take ownership of tasks from start to finish - Comfortable making phone calls and communicating through WhatsApp and email - Strong research and recommendation skills - Able to distinguish between urgent tasks, backlog items, reminders, and tasks you should own - Comfortable managing both personal and business administration - Highly organized without creating unnecessarily complicated systems - Comfortable working across time zones (SAST-aligned availability required) - Discreet and trustworthy with private business and personal information - Comfortable using AI and other tools for efficiency, while checking accuracy before submitting work This Role Is Not a Fit If - You need step-by-step instructions for every task - You wait to be reminded before following up - You send long lists without making a recommendation - You complete only the literal instruction without considering what happens next - You are primarily a general VA who is still learning how to become an EA - You are uncomfortable taking responsibility for open tasks and unresolved issues - You do not use Apple devices or cannot access Apple Reminders - You have never worked hands-on inside Shopify Hours We will begin with approximately 10 hours per week. Hours may increase to 15+ per week if you consistently reduce my workload and take meaningful ownership. Budget $20–$25 per hour, depending on proven experience and quality. I care more about judgment, ownership, and execution than choosing the lowest hourly rate. Hiring Process 1. Application review 2. Short interview 3. Paid practical test 4. Two-week paid trial 5. Ongoing long-term position for the right person Application Questions Please answer each question directly. Generic cover letters will not be considered. 1. How many years have you worked directly as an Executive Assistant to a founder, executive, or entrepreneur? 2. Briefly describe the person or business you supported and what you independently managed. 3. Do you own an iPhone or have active access to the Apple Reminders app? (Yes/No — this is a hard requirement.) 4. Describe your hands-on experience using Shopify. What specifically have you done inside the platform? 5. What are your normal working hours in SAST (South Africa time), and what other client commitments do you currently have during those hours? 6. How quickly do you normally acknowledge time-sensitive messages during your working window? 7. Give one specific example of a problem you noticed and solved before your client asked. 8. Give one example of a task you owned from beginning to end with limited instructions. 9. How do you track unfinished tasks, follow-ups, waiting items, and decisions needed from your client? 10. A trip is cancelled, but reminders and purchases connected to it remain scheduled. What would you do? 11. A customer-support bot tells a customer that a refund will be processed, but the bot cannot issue refunds. What would you do next? 12. Why are you applying for an Executive Assistant role rather than a general Virtual Assistant role? Please begin your application with the words: SECOND BRAIN