Executive Operations Lead / Chief of Staff

Executive Operations Lead / Chief of Staff
Location: Los Angeles or Puerto Rico preferred, flexible for the right candidate
Compensation: DOE
Part-time to start with opportunity to grow into full-time

About the Role

We are seeking a high-level operator to serve as the right hand to an entrepreneur overseeing multiple companies, investments, real estate developments, and private interests. This is a senior execution role for someone who can bring order, move priorities forward, solve problems quickly, and operate with discretion.

This person will act as a force multiplier across business operations, executive priorities, projects, vendors, staffing, and special initiatives. You must be highly competent, resourceful, calm under pressure, and able to independently drive outcomes.

What You’ll Oversee
Executive Support & Strategic Execution

• Manage shifting priorities across multiple businesses and personal interests
• Keep owner organized, informed, and focused on highest-value matters
• Handle sensitive matters with professionalism and discretion
• Draft communications, coordinate meetings, and ensure follow-through

Operations & Business Management

• Oversee vendors, contractors, consultants, and key service providers
• Build systems, processes, trackers, and accountability measures
• Coordinate bookkeeping, legal, payroll, HR, insurance, and compliance workflows
• Identify inefficiencies and solve operational issues quickly

Real Estate & Projects

• Support active construction, development, and property initiatives
• Coordinate architects, attorneys, engineers, PMs, designers, and contractors
• Track budgets, contracts, invoices, deadlines, and approvals
• Protect ownership interests through strong oversight and follow-up

Hiring & Team Oversight

• Assist with recruiting, onboarding, and managing team members
• Hold vendors and staff accountable to standards
• Improve communication flow and execution discipline across teams

Ideal Candidate

• 7+ years in Chief of Staff, Executive Assistant, Operations Director, Family Office, or founder support roles
• Strong business judgment and common sense
• Excellent written and verbal communication
• Highly organized without being bureaucratic
• Comfortable managing multiple moving parts simultaneously
• Assertive when needed, polished always
• Understands urgency, confidentiality, and ownership mentality

Strong Preference For

• Experience supporting founders, UHNW individuals, or family offices
• Experience with real estate, construction, or multi-entity businesses
• Familiarity with contracts, budgets, and vendor negotiations
• Able to travel occasionally and be available when priorities require it

This Role Is For You If

• You solve problems without being asked twice
• You hate loose ends
• You think like an owner
• You can handle pressure without drama
• You make chaotic environments run smoothly

Pay: $2,000.00 - $7,500.00 per month

Work Location: Remote