Executive Personal Assistant
4 days ago
Sunnyvale
Executive + Personal Assistant Location: San Francisco, CA 60% PA | 40% EA Position Overview • We are seeking an exceptional Personal + Executive Assistant who loves taming chaos so the executive can focus on what he does best., • 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 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., • Own end-to-end personal and professional travel: research, booking, itineraries, ground transportation, and contingency planning., • 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., • 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., • 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., • Slack (internal team coordination)., • Project & Task Tools: Asana, Notion, Todoist, Linear, ClickUp, or similar., • Scheduling Tools: Calendly, Cron, Vimcal, or equivalent., • Travel Tools: TripActions/NAVAN, Google Travel, airline portals, Uber/Lyft., • File & Knowledge Systems: Notion, Dropbox, Google Drive organizationCompensation and Benefits, • Compensation: $150,000-$220,000 base salary depending on experience and seniority., • Healthcare benefits + Dental and vision., • Occasional travel