Chief of Staff
Hawaii, Kailua-Kona
Posted 1 year ago


Super active, busy family are in need of an experienced Chief of Staff (MINIMUM 7 YEARS OF EXPERIENCE) to manage properties in Kailua-Kona, Hawaii, with travel and management of other properties around the US. Must be on site in Kona, for work, and travel with the family as needed, often with short notice. Hawaii would be your primary residence. Family will pay for all accommodations in other locations outside of Hawaii when working or traveling with them.

Seeking either local Kona/Hawaii candidates however, clients will offer relocation assistance for candidates on the mainland (off Hawaii). No housing will be provided, and this is not a live-in position. The candidate understands they are responsible for finding their own housing and paying for it in Hawaii (you must live on Kona). Client will not offer housing allowance, relocation allowance is provided only.

As the Chief of Staff you will have experience related to managing staff and travel; researching and booking travel arrangements. Handling shipments of supplies, and furniture to other residences. Inventorying, stocking and procuring for each residence (multiple). Management of staff at the homes, hiring new employees and training to the family’s standards. Walking the properties and communicating with on-site House Managers to ensure the home and systems are running correctly and cost-efficiently. Creating punch lists and following through on outstanding items before being asked about them, setting up systems and new applications that will create a better running team. Working cohesively with all involved, managing with mindfulness, kindness and with a hands-on leadership style, willing to do any job even if not within your “job description”.

An easy going personality is good here however, family do appreciate formality and boundaries and expect you to maintain a friendly not familiar mentality. This is not a suit/tie job, the family personally maintain a casual atmosphere but you should be able to switch on/off for meetings with vendors and know when to dress up/down. Understanding of private travel and what that entails (ensuring staff traveling with family have all that they need and that family are aware of any communication/changes to schedules, etc.). Advancing homes for their arrivals and closing down after departures.

Observing for the first month (or so) until you are familiar with how the family work with staff and in their own life is imperative, there is a casual urgency to getting started but not reinventing the wheel in the first few weeks. Earning the trust of this family, offering them confidentiality, and protecting their privacy is required of this position. Ability to work with multiple family members who may require different leadership styles – going with the flow – and figuring out the solution without adding to any stress is a key personality trait for the success of this position.

Experience with UHNW employers is required. Minimum of 7+ years of consistent experience (no job hoppers please).

Location: Kailua-Kona, HI (off island and surrounding islands are encouraged to apply but must be open to living on Kona full time). Management of other US properties/travel required.

Start Date: Hiring Immediately

Schedule: Monday through Friday – flexible with hours and must be on call (weekends and evenings will be needed)

Salary: $200k+ depending upon experience, no health benefits offered at this time. Bonus is at the discretion of the employers.

Must pass full background and reference check

Job Features

Job CategoryClosed Job
Salary200k DOE

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