Chief of Staff
Miami
30-03-2026
Job Type
Permanent
Emp Type
Full Time
Division
Business Support, Executive, Private
Job Title
Executive Assistant, PA, Chief of Staff, Chief of Staff (Family Office)
Salary Type
Annual
Salary
USD $250,000.00 - USD $350,000.00
Job ID
159653
Job Description
Job Title: Chief of Staff to CEO/Founder
Location: US (remote) or Cayman Islands (office-based)
Salary: $250,000 – $350,000
Location: US (remote) or Cayman Islands (office-based)
Salary: $250,000 – $350,000
We are looking for an exceptional Chief of Staff to support a dynamic CEO/Founder who is based between the US & Cayman Islands. This is a rare opportunity to step into a pivotal, high-impact role at the heart of a fast-moving and globally recognized organization.
This position combines true Chief of Staff responsibilities with high-level executive and personal support. It requires absolute discretion and the ability to operate seamlessly in a 24/7 environment. The successful candidate will act as a trusted right-hand and strategic sounding board, while also ensuring the CEO’s professional and personal life runs smoothly.
Key responsibilities:
- Serve as a strategic partner and confidant to the CEO
- Act as a sounding board on high-level decisions and strategic direction
- Oversee and coordinate complex projects on the CEO’s behalf
- Provide comprehensive EA/PA support including meticulous calendar and inbox management
- Coordinate complex global travel (including private jets, accommodation, and last-minute changes)
- Manage and hire private staff as required
- Oversee both business and personal logistics with absolute discretion
- Be willing to operate hands-on when needed - no task too big or too small
Key requirements:
- Extensive experience supporting a UHNWI in a true right-hand capacity
- Proven ability to move seamlessly between strategic work and hands-on PA/EA tasks
- Competency in AI & automation is essential
- Prior experience supporting a senator on Capitol Hill (DC) is preferred
- Experience operating as a Chief of Staff is preferred
- Proven ability to work around the clock and remain composed under pressure
- Highly discreet, emotionally intelligent, and strategically minded
- Entrepreneurial drive and mindset
- Willing and able to travel
- Graduate from a top university
Please only apply if you have the right to work in the US or the Cayman Islands.
REF: DM159653