The Chief of Staff (COS) serves as the point person for the Principal and is responsible for maintaining the Principal’s calendar and supporting her in lifestyle, property portfolio, philanthropic endeavors, special projects, events, and family logistics. This role will proactively and accurately communicate the Principal’s needs to the teams that support her. This client-facing role will manage the remote Executive Assistant, and collaborate with colleagues, service providers, and advisors to support delivering all personal administrative and residential services to the Principal. This role will assist the Principal in benchmarking, documenting, and ensuring exceptional service delivery in calendaring, creative services (i.e., gifting to events), executive and personal assistant support, and general and special project administration. This role will serve as a gatekeeper and liaison for the organization and Principal.
The primary goal of the COS is to ensure that the Principals make the most of their limited time, that information arrives at the right point in their decision-making process, and that follow-up happens without them having to check. The COS will build and maintain relationships with external professionals and vendors, acting as the first point of contact to the Principal as required. The COS will collaborate closely with the Managing Director, Estate Manager, Lifestyle to Culinary Manager, Family Assistant, Chef, remote Executive Assistant, and management team to communicate the needs of the Principal proactively and accurately to the teams that support them throughout their residential and commercial portfolio. The residential portfolio includes primary and guest residences in Montecito, CA, a beach home on Santa Cruz, and other domestic homes on the Gaviota Coast. The for-profit portfolio comprises an ultra-luxury boutique villa in Mexico and a luxury boutique ranch and wilderness experience in Colorado. The COS will work on-site at the Montecito, CA primary residence, providing coverage Monday – Friday and as needed on weekends and evenings. This role requires travel as it is necessary to support the Principal. The COS will also be responsible for event logistics and coordination alongside the Managing Director, the Lifestyle to Culinary Manager, and the management team.
This individual will demonstrate poise under pressure, take direction gracefully, and be driven by fluid communications and operations. Character attributes in this role include consummate critical thinking skills, unflinching accountability, common sense, and the ability to distill complex information into concise and prioritized communications. Must possess an innate ability to proactively manage the Principal’s expectations and bring a flexible, solution-oriented approach to their work. Ideal candidates will have significant former experience supporting busy, entrepreneurial, intellectually curious, and family-focused principals who strive to balance competing demands. The Principals value candidates with developed self-awareness, discretion and EQ, good judgment, proactive work ethic, collaboration, reliability and accuracy, and efficient communication skills.
From a values perspective, the Principals aspire to have an organization whose members are exceptional, always professional, and strive toward the following three forms of sustainability: (1) economically smart stewards of the dollar; (2) eco-sustainability – are stewards of the earth; (3) personally sustainable – are stewards of ourselves and those around us. As professionals, the Principals envision an environment where the organization’s members strive to be exceptional, to be of service, and to be themselves. They seek to encourage a deliberate mindset where the team is empowered to pause, think, and ask themselves if their approach to a task is the smartest way to do it.
This role will take a stewardly approach to ensure that the team constantly embodies and fosters the family’s values inside and outside the organization.
ESSENTIAL DUTIES AND RESPONSIBILITIES
GENERAL RESPONSIBILITIES
● Anticipation to Consistency – Work with and manage the remote Executive Assistant to provide personal,
executive, and administrative support in all areas of the Principal’s life. Anticipate the Principal’s needs and take immediate, thoughtful action in a logical sequence. The COS anticipates problems and is especially sensitive to issues that require diplomacy.
● Communication
○ Be an “air traffic controller” for the Principal regarding the flow of information. Communicate
actively with the Principal to ensure that all upcoming and outstanding projects and events are
proactively managed and that issues are promptly identified, addressed, and resolved.
○ Connect workstreams that might otherwise remain siloed.
○ Be an honest broker when the Principal needs a wide-ranging view without boundary
considerations.
○ Participate in daily weekly meetings with the Managing Director, the remote Executive Assistant,
and the management team to review projects, events, travel, Principals and family calendars, and
staffing schedules.
○ Prepare a weekly Pending Report for the Principals.
○ Collaborate with the property and household services teams to coordinate project events and
elevate workflow. Communicate clearly and consistently with all property staff and all off-site partners. Ensure the interior team is current on upcoming activities, including events, guests, and timing of activities.
○ Compose “on-brand” communications representing the Principal’s taste, style, and values.
● Foster Relationships to Interface—professionally represent and interface with the Principals’ family,
colleagues, clients, collaborators, and other important personal and professional advisors.
● Coordinate and Collaborate – with outside organizations, entities, governmental officials, security teams,
and event planners as required; maintain meticulous management of guest lists and RSVPs.
● Standard Documentation—In collaboration with the remote Executive Assistant, assist in developing and
maintaining manuals, procedures, and checklists for operations, events, travel, etc., and conduct annual reviews and updates.
ADMINISTRATIVE RESPONSIBILITIES
● Principal Calendar Management – Work closely with and manage the remote Executive Assistant to
provide accurate and timely management of multiple dynamic calendars, including personal appointments, meetings, events, and property schedules. Coordinate with the Managing Director, the Lifestyle to Culinary Manager, and the Estate Manager to confirm property visitation occupancy schedules and related stay details.
● Document, track, and prepare – Work closely with and manage the remote Executive Assistant to provide all pertinent information required for meetings. Maintain the accuracy of the Principal’s contact database.
● Travel Planning to Logistics – plan and execute travel itineraries and coordinate with residential property managers.
● Financials – Work with the CFO and assist in managing tracking expenses and bills, reconciling credit cards, approving staff expenditures, and coordinating with accounting partners. Perform light financial analysis as requested. Review contracts pertinent to the Principal.
● General Administration Support—Work with the remote Executive Assistant and the family’s personal assistant to assist Principals with general administrative processes, including daily mail receipt, record, and distribution; filing; scanning; photocopying; drafting outgoing correspondence; and proofreading material.
● Special Projects – Work with and manage the remote Executive Assistant to assist with overseeing projects as assigned, including holiday preparations, maintenance of archives, memorabilia, and business venture-related information.
● Event Management—Work with and manage the remote Executive Assistant and collaborate with the Managing Director and the management team on logistics coordination, planning, organization, and seamless orchestration of small- to large-scale events.
● Gifting to Product Research – Collaborate with the Principal on the gifting program, including inventory, researching unique gifts, tracking, purchasing, wrapping, and sending gifts. Work with the remote Executive Assistant on desired outcomes and processes.
● Wardrobe to Personal Items – help coordinate purchases, returns, and repair requests for the Principal and delegate what can be done by the remote Executive Assistant.
QUALIFICATIONS
EDUCATION to EXPERIENCE
● A bachelor’s degree and a minimum of five-plus years of relevant experience or equivalent combination of education and experience providing executive personal support within a high-service, action-oriented private environment with high accountability levels.
● Experience coordinating with diverse personal service and hospitality teams, including business and personal assistants, housekeepers, chefs, and other staff vendors as may be required.
● Experience maintaining a private employer’s confidentiality, safety, security, and privacy.
● Tech-savvy: Advanced knowledge of both Google and Apple products, demonstrable proficiency with
Google Suite (calendar, drive, sheets, docs), calendaring programs, Zoom and other online video communication software, PM messaging tools, and quick learning of new apps. Familiarity with the Monday app.
● Must have experience supporting complex travel, hospitality, event, and entertaining requirements.
Personal Qualities to Character
● Warm, polished, poised, intuitive, respectful, calm, and collaborative by nature.
● Exceptionally organized, intelligent, dynamic, confident, natural multi-tasker, and resourceful.
● Can anticipate and avert problems.
● Does strategic thinking and problem analysis.
● Can manage the process of ideas to execution.
● Is observant and attentive to the Principal’s preferences and intuitive at replicating the qualities they
enjoy.
● Displays humility, maturity, and situational sensitivity.
● Has a can-do attitude, no task being too great or too small, and genuinely enjoys providing personal
service.
● Capable of easily juggling competing deadlines while remaining calm and attentive to detail and accuracy.
● Ability to anticipate the next steps by thinking creatively, solving problems, and taking a broad perspective to make the principal’s life easier. Takes ownership of work; thinks strategically and is resourceful.
● Superb written and oral communication skills; a gift for distilling information into verbal and written formats.
ADDITIONAL INFORMATION
● Work location: This role will be on-site in Montecito, CA.
● Compensation: $200,000k DOE plus benefits
● The family has pets, and the candidate must be comfortable around pets.
● All qualified finalists require verifiable references and a thorough background check.
