Executive Assistant & Personal Operations Lead
Location: Remote
Type: Full-time
Start Date: Immediate
Position Overview
Seeking an experienced Executive Assistant to manage both professional and personal operations (50/50 split). You will act as my central operating system: managing workflows, optimizing my time, and helping track the details of both work and life. This role requires strong organizational skills, discretion, and the ability to work autonomously while maintaining close coordination.
Core Responsibilities
Professional Operations (50%)
- Calendar & Inbox Management: Save me time. Scheduling based on core preferences
- Research & Synthesis: Investigate business topics or markets; deliver concise, decision-ready summaries.
- Project Tracking: Own follow-ups and deliverables. If I say "remind me in three months," it happens.
- Clear Workflow Management: create a full archive of key workflows, data, reminders, and information needed to minimize unnecessary back and forth
Personal & Lifestyle Management (50%)
- Travel & Scheduling: Manage flights, hotels, itineraries, reservations, and personal appointments.
- Vendor Coordination: Oversee household contractors, services, and subscriptions. When something breaks, you handle the coordination.
- Procurement: Research purchases, present options with clear comparisons, and manage ordering.
- Financial Admin: Light expense tracking, bill pay, and personal finance organization.
Major Life Events (Collaborative)
Wedding:
- Research and vet wedding planners; coordinate interviews
- Once selected, manage planner communications, decision tracking, and file organization
- Maintain guest list database and RSVP tracking
Baby (Due July):
- Research and screen night nurses, doulas, and household support
- Track prenatal/postnatal calendar; assist with insurance claims and medical billing
- Manage baby gear research, purchasing, and delivery coordination
Requirements
Tools & Technology
- Comfortable using AI tools (ChatGPT, Claude, Perplexity) to draft communications, summarize documents, and accelerate research. Know how to rely on AI, but how to use it as a tool
- Proficient with modern productivity platforms: Notion, Slack, Superhuman, 1Password, Linear, Google Workspace (or ability to learn quickly)
- Automation-minded—if a task is repetitive, you find ways to streamline it
Ideal Candidate
- Experience: 2–5 years in Startup Ops, Executive Assistant, or similar high-demand role
- Schedule: Must have significant overlap with EST business hours (we're based in Miami)
- Work Style: Proactive problem-solver; you catch small issues before they escalate
- Discretion: High EQ; experienced handling confidential matters
- If Miami-based: Familiar with the area, valid driver's license, able to handle occasional in-person errands (property checks, mail, vendor access)
To Apply
Please send your CV to SALThiring@proton.me alongside a description of relevant work experience and an overview of your typical workflow and systems setup.
Share a time where you had to navigate a particularly challenging problem related to EA/PA work, and how you went about solving it step by step.
