Executive Assistant to Chief of Staff
 
Location: Ojai, California (Operating Remote)
Reports To: Lead Principal
 
OPPORTUNITY OVERVIEW
We are seeking a highly capable Executive Assistant Chief of Staff to support the lead principal overseeing a complex portfolio of private, business, philanthropic, and creative initiatives.
This role serves as the central operational command layer across business, household, and property operations. The Executive Assistant Chief of Staff is responsible for transforming fragmented information across multiple systems into clear, structured execution while enforcing accountability across all stakeholders.
The role supports the lead principal with oversight of estate operations, project execution, organizational planning, coordination and communications across multiple project owners.
This is not a traditional administrative assistant role. The position functions as a central operational coordination role within a fast-moving ecosystem of projects, properties, stakeholders, budgets, approvals, and priorities.
The successful candidate will become a trusted operational partner responsible for bringing clarity, accountability, structure, and follow-through to a diverse and evolving set of initiatives.
This is a high-trust, high-agency role requiring ownership, judgment, and independent decision-making.
 

ABOUT THE ENVIRONMENT
The estate portfolio spans multiple active workstreams, including:
• A private micro-school serving approximately 13 children ages 5–12
• A high-end executive retreat center focused on transformational experiences, overnight stays, wellness, hospitality, ceremonies, and curated programming
• A creative media initiative including a filmed first episode of a celebrity reality-show with additional episodes and development in progress
• Multiple family estate and household operations across several locations
• Philanthropic, legal, financial, administrative, and construction initiatives
• Cross-functional teams spanning operations, household management, finance, legal, construction, guest experience, staffing, and creative production
 
CORE PURPOSE OF THE ROLE
The Executive Assistant Chief of Staff helps bring order, visibility, accountability, and follow-through across a multi-project environment.
This person acts as a trusted extension of the principal, ensuring priorities move forward, communication remains organized, stakeholders remain aligned, and all systems reflect reality.
 
CORE RESPONSIBILITIES
• Own master calendar, communication, and operational coordination
• Translate conversations into structured execution
• Maintain alignment across all systems (Slack, ClickUp, Calendar, Documents, Finance)
• Interface and coordinate directly with internal project managers and external vendors as needed

KEY RESPONSIBILITIES
 
Executive Support
• Manage calendars, scheduling, meeting coordination, reminders, and follow-up
• Prepare agendas, summaries, and briefing materials
• Track commitments and outstanding decisions
 
Operational Support
• Support estate, retreat, and business logistics
• Track urgent approvals and implementation gaps
• Assist in cross-functional planning tied to budgets, staffing, and launch readiness
 
Financial Coordination
• Organize invoices and expense documentation
• Coordinate vendor payments and approvals
• Support financial reporting coordination with bookkeepers or accountants
 
Project Management
• Operate within project management systems to monitor project progress and task flow
• Organize documentation, checklists, agreements, and procedures
• Draft professional emails, summaries, and internal updates
 
 

SYSTEMS to TOOLS ENVIRONMENT*
Candidates must demonstrate their experience and ability to operate across multiple technology systems. Please share your experience with these or similar systems:
• Slack Teams Zoom (communications)
• ClickUp or similar (task to project management)
• Microsoft 365 (calendar, email, Teams)
• SharePoint Egnyte (documents)
• Ramp Expensify Sage (financial tools)
• The Nines (property operations)
• Trainual, MyGlue, DocuSign, Earth Class Mail, Otter AI, GoDaddy, Cellgate
 
CORE OUTPUTS to OPERATIONAL CADENCE
Daily
• Calendar Updating to Multi-Calendar Synchronization
•Daily Task to Activities Brief (priorities, actions, follow-ups, decisions)
• Pre-meeting agendas with attendees, speaking time allocation, topic points, and meeting objective(s).
• Post-Meeting follow-up briefs with attendees, outcomes, next steps, task assignments, ownership, to due date
• Invoice approvals and payments and basic bookkeeping entries
 
Weekly
• Weekly Operations Brief (calendar, travel, staffing, schooling, priorities list)
• Monday Meeting: Team Planning project alignment assignments
• Friday Meeting: Team Reporting status updates requests
Monthly
• Monthly calendar overview and forward planning
• Monthly calendar overview across properties and operations
•Monthly financial updates and budgeting meeting
 
QUALIFICATIONS
• 5plus years in executive support or operations
• Experience supporting founders, investors, principals, or senior executives
• Strong systems thinking and tool fluency
• High ownership and independent decision-making
• Excellent communication and organization
• Ability to manage complex, multi-project environments
• High discretion with confidential information
• Strong judgment and initiative
• Ability to self-manage, upward-manage, and operate under ambiguity
• Comfortable working independently in a remote environment
 
PREFERRED EXPERIENCE
• Family office or estate operations
• Retreat or hospitality operations
• Education administration
• Creative or media production
• Legal or finance-heavy operational environments
• Construction or property development coordination
• Experience building SOPs, dashboards, and operational systems