OVERVIEW

A private, philanthropically active family seeks a Chief of Staff to serve as the single point of operational ownership across their residences, household team, and day-to-day financial administration. The family's life runs across a primary residence in Middle Tennessee and additional properties in seasonal rotation, alongside a charitable fund and an active travel calendar. The standard throughout is resort-grade hospitality: every residence performing at that level whether the family is in it or not.

This is the first hire of its kind for the family, and it carries genuine authority. The person in this seat will hold the complete picture of the operation, from financial administration, insurance, and property decisions through vendor performance and the correspondence and calendars of both principals. They will also build the infrastructure that runs it: property manuals, service standards, position descriptions, payroll, and the technology stack behind all of it. Much of that structure does not exist today, which means this role is defined by what its holder builds rather than what they inherit. The seat is resourced, not isolated. A hands-on House Manager / Personal Assistant reports to this role and carries the daily rhythm of the home, keeping this seat on the operation itself and on the decisions only this level can make.

The principals are first-generation and self-made, and it shows in how they operate. They are warm and casual in tone, exacting in standard, and accustomed to doing things themselves, which is precisely why they notice when something is done well. They value privacy, trust, service, and discretion. Family comes first, decisions are made jointly and quickly, updates are short and summarized, and feedback runs direct in both directions. They want someone capable, competent, and kind who fits that culture instead of managing around it, and who earns the trust to run the operation without being checked. This is a seat for someone who wants to give a family back their time and take real ownership of a life at scale.

EXPECTATIONS

Five or more years as a chief of staff, estate manager, or director of residences to an ultra-high-net-worth principal or single-family office.
Multi-property portfolio ownership, including seasonal openings and closings, advance work ahead of family arrivals, and scheduling maintenance and construction during periods of non-residence.
Vendor sourcing, contracting, insurance coordination, and performance accountability, including holding service standards at properties where the principals are not physically present.
Day-to-day financial administration: bill pay, household and property accounting, and execution, tracking and budgeting to create greater transparency.
Entity, trust, and philanthropic administrative support in coordination with the family office and outside legal counsel, with ownership of the big picture across all of it.
Household staff leadership: direction, scheduling, performance management, and hiring of the household team, if needed, along with the position descriptions, manuals, and standard operating procedures that do not exist today.
Employment infrastructure: payroll, benefits evaluation and implementation, and state and federal compliance for a small household staff.
Administrative and financial oversight of private aviation in coordination with an existing management partner.
Inbox and calendar ownership for two principals, including remediation of a significant existing email backlog and full removal of technology friction.
Technology self-sufficiency: selection and implementation of estate management, home automation, security, and financial platforms, with no reliance on the principals for technical support.
Reporting discipline: a standing weekly meeting, exception-based escalation, and decisions brought forward with a recommendation attached rather than a question.
Valid driver's license and willingness to travel to additional properties as required.

WHO YOU ARE

Anticipatory rather than reactive. You predict the future and see around corners.
Genuinely autonomous. You take a problem, solve it, and report the outcome rather than the process. You do not need hand-holding, a playbook, or a second ask.
Uncompromising about standards, in yourself and in every vendor you manage. Good enough is not a standard you recognize.
Humble and low ego. Comfortable moving from a financial review to stocking a refrigerator in the same afternoon, with no task beneath you.
Warm in tone and formal in standard. You read the room, you know where the boundary sits between family member and employee, and you never insert friction between two principals who operate as one.
Proactively detail-oriented and willing to execute solutions. You notice the damp cushion, the dirty car, and the dusty corner before anyone has to point at them.
Disciplined about follow-through. Nothing is asked twice and nothing is chased.
Lean by instinct. You solve with structure and accountability before you solve with headcount. If new headcount is needed, be able to create a strategic business proposal and present it to the Principals.
Comfortable building in ambiguity, in an environment with no manual, no position descriptions, and no established cadence.
Absolute discretion and privacy, on and offline, at all times. This is mandatory and without exception.

PREFERRED

Strong preference: Prior experience in luxury hospitality at the five-star or ultra-luxury resort tier, a strong signal for the service standard this family expects.
Experience as the first professional hire into a family that has managed itself, including building structure where none existed.
Portfolio experience across geographically distributed residences with seasonal rotation and periods of non-residence.
Familiarity with multi-family office structures and the regulatory boundaries that limit what an outside firm can execute.
Foundation, charitable fund, or grant administration exposure.
Working fluency with estate management platforms, home automation, security systems, accounting and bill-pay tools, Google Workspace, Microsoft 365, and AI tools.
Experience standing up payroll and benefits for a small household staff.

RESPONSIBILITIES

Property and Vendor Management: Own every residence end to end. Proactive oversight rather than reactive repair, vendor selection and accountability, insurance coordination, and a documented standard of care that holds whether or not the family is watching. Schedule maintenance, construction, and deep-cleaning cycles during periods of non-residence so the family never arrives to unfinished work.

Advance and Close-Down: Prepare each property ahead of the family and close it behind them. Open the home, verify systems and security, confirm grounds, pool, and outdoor furnishings are ready for the season, stock the kitchen to preference, and leave nothing for the principals to notice on arrival.

Financial and Entity Administration: Run day-to-day accounting and bill pay in partnership with the family office. Own insurance and the execution items the outside firm cannot hold. Work alongside the family office and outside counsel so that nothing falls through at the entity, trust, or philanthropic level.

Principal Support and Correspondence: Own inbox and calendar for both principals. Clear and hold the existing email backlog, structure the week ahead, and absorb technology entirely on behalf of the principal.

Household Team Leadership: Direct the household team, including household support and houseman, who reports to this seat. Set the checklists, cadences, and service standards that keep quality consistent in the family’s absence, hold the team accountable to them, and make candid recommendations on structure as the operation matures. Execute on tasks to ensure a seamlessly running household.

Systems, Structure, and Standards: Build the operating infrastructure that does not exist today: property manuals, position descriptions, vendor scorecards, service standards, and the technology stack to run them. Establish employment infrastructure, including evaluating and standing up payroll and a benefits structure.

Philanthropic and Special Projects: Support expanded engagement with the family's charitable fund, including grantee meetings, materials, and next-generation involvement. Bring a newly completed property fully online across furnishings, systems, and vendor bench, and establish a management cadence for the additional properties in rotation.

Reporting Cadence: Both principals are involved and they decide together. Hold a standing weekly meeting covering issues, opportunities, and the decisions only the principals can make, supported by a short weekly look-ahead of movements, guests, family visits, and the state of each property. Escalation is exception-based: if it is handled, no update is needed. Decisions come forward with a recommendation attached rather than a question.

Scope Boundary: This seat manages household and administrative operations and performs them. Daily hands-on execution, including housekeeping oversight, errands, wardrobe and pantry management, and personal support, may be required and assisted by household support. The attitude, however, is that no task is too small. When the moment requires it, the person in this seat handles it themselves.

Confidentiality and Discretion: Uphold the utmost confidentiality and discretion at all times, across the family, the residences, the travel calendar, and the family business. A non-disclosure agreement is required.

COMPENSATION

Compensation: $150,000 to $225,000

Healthcare: To be determined

Relocation: Open to discussion for the right candidate

Confidentiality and Background: Non-disclosure agreement required before client interviews. Standard background check, references across recent direct reports, peers, and principals, and a behavioral and credibility assessment for finalists

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