High Agency Executive & Personal Assistant (EA/PA) — "Second Brain"

Location: Global Search with B2 German language proficiency (Italian is a 2nd preference)
Hours: 9AM - 3PM Approximately 20 hours per week (Part-Time) on average, with rare weekend Adhoc tasks for roughly 2 hours.
Growth: The potential to scale to Full-Time (40 hours per week) if the candidate is the right organizational fit and can proactively absorb more portfolio tasks.
Compensation: $1,300 USD/month (subject to experience, model setup, and final hour commitments).
Dual-Role Compatibility: If hired part-time, the candidate is permitted to hold another part-time role, provided it does not compromise response rates, availability, or the ability to prioritize urgent requests.

Role Overview

This is a highly dynamic hybrid High Agency Executive and Personal Assistant (EA/PA) role supporting an entrepreneurial principal managing a diverse portfolio, including a family office, a charitable foundation, private investments, and a private wine-producing estate in Italy.

Rather than executing a list of static, repetitive tasks, you will act as a "second brain" and a proactive problem solver. You are someone who can take a broad objective, figure out the path from A to B, anticipate hurdles, and present fully formed solutions autonomously.

Key Responsibilities

1. Operations & Lifestyle Management

Complex Travel & Itinerary Planning: Go beyond standard bookings. If the principal travels to a city, you will strategically map out their schedule, coordinate meeting locations, manage restaurant/entertainment reservations based on their preferences, and handle logistical logic (e.g., proximity and timing).
Personal Concierge & Local Outreach: Coordinate personal and household logistics, requiring direct outreach to vendors, mechanics, or service providers.
Special Projects: Research, source, and coordinate unique tasks, such as finding and vetting vintage cars, researching lifestyle services, or handling Airbnb/hospitality bookings against strict quality categories.

2. Business & Family Office Support

Multifaceted Portfolio Assistance: Provide administrative support across the principal's family office, upcoming charitable foundation, and wife’s projects.
Light Financial Administration: Assist with basic structuring, billing, accounting coordination, and cross-border project paperwork as needed.
Wine Estate Coordination: Assist in ad-hoc administrative or marketing support related to the principal's wine production property in Italy.

Key Requirements & Qualifications

Language Proficiencies (Critical)

German (Minimum B2 Proficiency): Crucial for day-to-day coordination. You must be comfortable picking up the phone to call traditional, local businesses or mechanics in Germany who may not speak English. (Native proficiency is not required, but conversational ease is necessary).
Italian (Highly Desirable Fallback): Proficiency in Italian is a major asset to assist with vendor management and operations for the property and wine estate in Italy.
English: Fluent written and spoken English for direct communication with the principal.

Core Competencies & Mindset

Proactive "Second Brain" Capability: You don't wait for step-by-step instructions. You can take an unstructured brain-dump of ideas, build a framework around it, and execute it end-to-end.
High Autonomous Drive: You possess the critical thinking to see subsequent steps ahead of time and bring recommendations rather than asking open-ended questions.
Adaptive to Taste: You have a keen eye for quality and are capable of quickly learning, internalizing, and applying the principal's personal style, ranking systems, and aesthetic preferences (e.g., hospitality, dining, lifestyle).
Resourceful & "Hungry": Attitude and cultural fit matter far more than decades of corporate experience. We highly welcome ambitious, high-bandwidth individuals who are eager to learn and grow within a multifaceted ecosystem.

High Agency Executive & Personal Assistant (German) - 61114189087