We are seeking an exceptional Personal + Executive Assistant who loves taming chaos so the executive can focus on what he does best.
This is not a traditional EA role, nor is it purely personal assistance. It sits at the critical intersection of business-adjacent personal work. You will primarily be managing the client’s household, business, family logistics, health, finances, and daily life. You will not be sitting behind a desk answering emails. You will be proactively solving problems before Caleb knows they exist.
Core Responsibilities
Household Management
Proactively manage household staff: identifying, hiring, and overseeing housekeepers, chefs, and other support personnel.
Coordinate home maintenance, service appointments, and keep all household systems running smoothly.
Manage Principal’s residence at the Ritz-Carlton Residences, building relationships, coordinating services, and keeping it guest-ready.
Personal & Family Support
Manage children’s schedules, school events, activities, and family logistics, including stepping in when other arrangements fall through.
Plan and coordinate date nights, special occasions, and personal celebrations.
Support dietary preferences and health-related logistics, including meal planning and ensuring Caleb has eaten at the right times.
Handle personal appointments, medical scheduling, and health optimization.
Manage gifts, buying and sending for personal and professional occasions.
Handle package deliveries, returns, and personal errands.
Travel Planning
Own end-to-end personal and professional travel: research, booking, itineraries, ground transportation, and contingency planning.
Proactively identify business-adjacent opportunities during travel, including investor meetings, strategic stops, and schedule optimization across trips.
Assets & Administration
Manage personal assets: vehicles (including ensuring cars are never out of fuel), insurance policies, renewals, and warranties.
Maintain organized filing systems, physical and digital, and process mail to ensure nothing is missed.
Support tax season readiness: ensuring documents and data are organized year-round so nothing is scrambled at year end.
Run personal family office coordination, covering financial reconciliation, working with CPAs and financial managers, and managing ongoing financial admin.
Executive & Business Support
Client & Investor Communications
Help manage and organize client and customer communications. This was one of the key failure points Caleb identified in a previous hire.
Maintain and manage ongoing relationships with portfolio company CEOs, founders, and investors on Caleb’s behalf.
Set up and maintain communication systems and processes for the fund.
Calendar & Operations
Manage and optimize calendar alongside Caleb’s existing AI-assisted systems, protecting time for strategic priorities.
Coordinate complex domestic and international travel with full itineraries and contingency planning.
Prepare briefing materials and logistics for speaking engagements, keynotes, and conferences.
Support office setup and systems as the team scales from its current 4–5 people.
Coordinate professional events, fundraising activities, and business entertainment.
Special Projects
Handle one-off projects and initiatives as they arise. Caleb runs a fund and things move unpredictably. You manage whatever needs managing.
Support the establishment and administration of a formal fund structure as White Rabbit formalizes.
Ideal Candidate Profile
Mindset & Character
Chief-of-staff mentality, not task-executor mentality. You manage multiple priorities simultaneously and nothing drops through the cracks, because catching the cracks is the job.
Hospitality-first instinct. You read situations and act before being asked. The whiteboard example above is not a metaphor. It is a literal description of how you operate.
Extremely proactive. Caleb should rarely have to tell you something twice. Ideally, he never has to tell you once.
Direct and execution-oriented. You move fast and follow through completely.
Warm and emotionally intelligent. You manage personal and professional relationships, including with family, vendors, founders, and partners — with care.
Low-ego in practice, not on paper. No task is beneath you.
Ready, not just available. This is not a 9-to-5 by nature. Caleb is not calling you every night, but when he needs you, you are there. He wants the comfort of knowing that.
Long-term oriented. He is looking for the person he wants for the rest of his career.
Experience & Background
Minimum 5-10 years supporting C-level executives, HNW individuals or principals at family offices
You have supported a high-net-worth individual, C-level executive, or principal in a blended personal/professional capacity before.
Experience in a fast-paced startup or early-stage environment is a strong plus. You know what wearing many hats actually means.
Background in consulting, family office, or a comparably high-execution environment is a plus
Tech-savvy and comfortable with productivity tools, communication platforms, and whatever systems are needed.
Technical proficiency:
Google Workspace: Calendar, Gmail, Drive, Docs, Sheets (expert-level required), Slides.
