Chief of Staff

A private client in Half Moon Bay, CA is seeking a highly experienced and proactive full-time Chief of Staff to support the principal across a mix of staff management and administrative and personal duties. This is an onsite, Monday–Friday roughly 9 : 00 AM–5 : 00 PM role based out of the principal’s private residence, with occasional travel and coordination across multiple properties. There is flexibility for the candidate to work out of the San Carlos office as long as they are also available and able to be onsite in Half Moon Bay as needed. The Chief of Staff will provide strong support to both principals, with a particular focus on supporting Mr. The ideal candidate is grounded, structured, warm, and highly professional—someone who is highly adept at creating and implementing new systems to build structure, can seamlessly navigate between independent problem-solving and collaborative teamwork in a discreet, fast-moving household. The role requires excellent acumen when it comes to online capabilities, including integration with AI tools like ChatGPT, fluency in direct messaging systems, and cross-platform calendar coordination. A seasoned Executive Personal Assistant ready to step into a Chief of Staff role would excel in this position, as duties also include booking international and domestic travel, vehicle maintenance, Airbnb accommodations, and other logistical support.

Job responsibilities include, but are not limited to :

• Provide direct administrative and personal support to the principal
• Heavy calendar management, scheduling, appointment coordination, and meeting logistics
• Plan and coordinate all travel logistics (domestic and international) create detailed itineraries, and family-related activities
• Actively assist with booking vehicle transport, reservations, and short-term rentals such as Airbnb
• Manage all communications, emails, and messaging platforms
• Implement and maintain systems to streamline personal and business workflows, including leveraging digital tools and automation
• Conduct independent research and execute requests with minimal oversight
• Interface with the Estate Manager and household staff as needed
• Provide administrative support across the family’s broader property portfolio
• Handle sensitive information with discretion and professionalism
• Offer support in a flexible and anticipatory manner to ensure seamless day-to-day operations
• Vehicle maintenance including coordinating detailing and keeping insurance and registration current
• Additional Administrative Personal Assistant tasks as needed and requested

Requirements :

Salary : $110,000–$150,000 / year, All salary offers are Depending On Experience, References, and the results of Federal Background Report

Benefits : 100% medical, dental, and vision coverage for the individual 80% coverage for dependents, 401(k) employer match, 15 PTO days per year, with potential to increase to 23, 10 paid holidays annually, 10–20% potential discretionary, performance-based annual bonus