Chief of Staff to the Principal: Multi-Entity (Remote)

About this role

Chief of Staff to the Principal: Multi-Entity (Remote)

Time: EST

About the role

I'm looking for a Chief of Staff to help me run operations across a small law firm, a real estate portfolio, a private company, and personal administration. The goal is to free me up to focus on the work only I can do, while you bring structure, follow-through, and a second set of eyes to everything else.

You'll work alongside me coordinating people, vendors, systems, and decisions, not in isolation. Expect a tight feedback loop, real ownership over time, and the autonomy to make calls within agreed-upon scope.

This role is for someone who has run things before, can hold their own across very different domains, and will tell me when I'm wrong. If you want a structured corporate environment with a defined playbook, this isn't it. If you thrive on context-switching, autonomy, and bringing order to complexity, keep reading.

What you'll help me run

Across all entities:

• Calendar, email triage, and prioritization across personal and business
• Vendor management: bookkeepers, accountants, contractors, attorneys, IT, insurance
• Expense tracking and coordination with my accountant
• Travel planning and logistics
• Meeting prep: agendas, briefing docs, follow-up tracking
• Project management on initiatives I'm driving but don't have time to run day-to-day

Law firm:

• Liaison with firm staff on operational matters
• Vendor and tooling oversight (practice management software, IT, billing systems)
• Reporting on key metrics to me on a regular cadence

Real estate / properties:

• Coordinate property managers, contractors, and tenants
• Track maintenance, leases, renewals, insurance
• Manage acquisition and disposition logistics with brokers and attorneys

Private company:

• Operational backbone: vendors, tools, recurring processes
• Support on hiring, contracts, and basic financial coordination

Personal:

• Household vendor management
• Personal sche...