Chief of Staff to CEO/Founder

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.

• 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.

• 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