The Calendar Group

Family offices

The office behind the family.

A family's world is larger than an org chart — the office, the residences, the philanthropy, the travel between them. We staff the people it all runs on, from a first executive assistant to the chief of staff who carries the whole map.

Begin a Confidential Search(877) 404-5290
A quiet, well-ordered morning
Fine textiles, precisely kept

Small teams. No room for a wrong hire.

A family office hire is different in kind, not degree. The team is small, the information is sensitive, and every person touches the principal's world directly. A great corporate résumé means little if the candidate needs an org chart to feel safe.

We have spent twenty-four years learning what does predict success here: comfort with ambiguity, discretion as a reflex, and the temperament to serve a family's interests without needing the spotlight. We interview for those qualities specifically — and we know how to verify them, because we know the references to call.

And because we staff the household as well as the office, we are the one firm that sees a family's world whole. The estate manager and the controller, the chief of staff and the chef — the seats depend on each other, and hiring them as if they don't is how offices end up rehiring. From a first executive assistant to a full build-out, we advise on structure and compensation before the search begins, and we stand behind every placement with a six-month replacement guarantee.

The roles

The roles a family office runs on.

Each with compensation ranges, interview questions, and the judgment calls that separate a plausible candidate from the right one.

Full role library

Family Office Executive Assistant

Senior administrative support inside a family office — where the calendar, the household, and the balance sheet meet.

The role, comp & interview guide

Family Office Chief of Staff

The senior executive who runs the family office itself — operations, people, and priorities across the family's world.

The role, comp & interview guide

Family Office Controller

The financial steward of a family office — books, reporting, controls, and the numbers you can actually trust.

The role, comp & interview guide

Private Chief of Staff

A senior operator who runs your personal world — staff, properties, projects, and priorities — so only true decisions reach you.

The role, comp & interview guide

Personal Assistant

The person who runs your day so you can live it — calendar, travel, correspondence, and everything unassigned.

The role, comp & interview guide

Estate Manager

The operational lead for a significant property — staff, vendors, budgets, and projects, so your home simply works.

The role, comp & interview guide

Placements that last

  • Estate Manager · Palm Beach, FL

    Managing a large estate portfolio — placed in 10 days, in the role for 1.5 years; several successful placements with the client

  • Director of Properties · Lake Forest, IL

    Managing a three-property portfolio — placed in 30 days, in the role for 5 years

The archive

Questions

Asked, answered.

Can you run a search without naming the family?
Yes — most of our family office searches run this way. Candidates see a profile of the office and the role; identifying details are shared only when a meeting is agreed, under NDA where required. Discretion is not a service tier. It is how we work.
Do you understand the difference between corporate and family office talent?
It is the center of our practice. Corporate stars often struggle in a family office — the structure they relied on isn't there. We screen for the specific temperament the environment demands: low ego, high ownership, and ease with work that crosses business and personal lines.
Can you help us define the role before we hire?
Yes, and we usually should. Many engagements begin with a structural question — do we need a chief of staff or an executive assistant, a controller or a bookkeeper? We advise on scope, title, and compensation first, because the wrong definition guarantees the wrong hire.
We need more than one hire — can you build the office?
Yes. Some of our most valuable engagements start before the first hire: what the office actually needs, in what order, at what cost. We have watched offices form for twenty-four years — from a single assistant carrying everything to a staffed operation across residences, investments, and philanthropy — and we will tell you plainly which seats to fill now and which can wait. Where a need falls outside our practice, we say so and point you to the right firm.
How do you handle compensation guidance?
We share current, market-specific ranges for every role we place, drawn from our searches rather than surveys, and we'll tell you honestly when an offer won't hold a great candidate. Retention is the number we care about — it is the only real measure of a search.

Family offices

Tell us about the office.

The structure, the gap, what the last person got wrong. One confidential conversation is enough to scope the search.

Prefer to talk? (877) 404-5290

Held in confidence. No obligation.