The Calendar Group

Hiring guide

Director of Residences

The senior executive over a portfolio of homes — setting standards, leading property managers, and answering to you alone.

Begin a search for this role(877) 404-5290

Compensation

$200,000–$350,000 base

Typical base compensation, major U.S. markets, 2026. Scope, travel, and household complexity move the range.

We advise on offer structure — schedule, housing, benefits, bonus — before every search. The right package is how great people stay.

A director of residences sits above the individual properties. Where an estate manager runs one home, the director runs the system: three houses in three states, each with its own staff, its own vendors, its own rhythm — and one consistent standard across all of them. Your linens are folded the same way in Aspen as they are in Palm Beach. Your arrival protocol never depends on which house you land at.

This is a leadership role, not a hands-on one. The director hires and develops the estate managers and house managers, consolidates budgets across the portfolio, plans capital projects on a multi-year horizon, and serves as your single point of accountability. One conversation, and the decision moves through every property.

Households typically create this position when a second or third significant residence starts pulling the principal back into operations. The right hire returns that time — and brings the kind of judgment that has usually been earned over fifteen or twenty years of private service.

What the role owns

  • Set service and operating standards across all residences
  • Hire, develop, and supervise property-level managers and senior staff
  • Consolidate and oversee budgets, reporting, and expense controls portfolio-wide
  • Plan and sequence capital projects and renovations across properties
  • Coordinate seasonal openings, closings, and principal travel between homes
  • Negotiate portfolio-level vendor and insurance relationships
  • Serve as the single operational point of contact for the principal and family office
  • Lead crisis response and continuity planning across properties

What great looks like

A great director builds one written standard and trains every house to it, so your experience is identical no matter where you wake up.

They develop the managers beneath them; the sign of a strong director is that the property teams get better even when the director is elsewhere.

They think in years, not weeks — sequencing renovations so no two homes are disrupted in the same season.

They work fluently with your family office, presenting consolidated numbers a controller can actually use.

They know which decisions to bring to you and which to simply make. Adequate directors escalate everything or nothing.

Interview questions worth asking

  1. 01

    How many properties and direct reports have you overseen at once, and how did you structure your week across them?

  2. 02

    Tell me about a manager you inherited who wasn't performing. What did you do, and how long did you give it?

  3. 03

    How do you keep service standards identical across houses with different staff and different cultures?

  4. 04

    Describe your capital planning process. How far out do you plan, and how do you present it to the principal or family office?

  5. 05

    What is the largest consolidated budget you've owned, and where did you find waste in it?

Questions

Hiring a director of residences, answered.

How is a director of residences different from an estate manager?
An estate manager runs a property. A director of residences runs the people who run the properties. The director sets standards, manages the managers, consolidates budgets, and plans across the whole portfolio. If you have one significant home, you need an estate manager. If you have several — and you're still the one connecting them — the director role is what removes you from operations.
When does a household need this role?
Usually at the second or third significant residence, or when a family office finds itself fielding property questions it isn't staffed to answer. The honest signal is your own calendar: if you're mediating between house managers, approving vendor invoices, or repeating the same instruction in three houses, the portfolio has outgrown its structure.
Should this person report to me or to my family office?
Either can work; what fails is ambiguity. We generally recommend the director report to the principal on standards and experience, with a dotted line to the family office on budgets and controls. Decide it before the hire and put it in writing — the strongest candidates will ask about reporting lines in the first conversation, and they should.
What background produces the best directors?
Most come up through estate management, often with an earlier chapter in hotel or club leadership. Look for someone who has already managed managers — running one large house well is not the same skill as running five through other people. Long references from principals, and from the staff who worked under them, tell you most of what you need.

Begin

Looking for a director of residences?

Tell us about the household and the role. A senior advisor — not a coordinator — will come back to you within one business day.

Held in confidence. No obligation.