Private Executive Assistant

About the Role

We are seeking a highly skilled Private Executive Assistant to support a dynamic entrepreneur, investor, and commercial real estate owner who operates between Massachusetts and South Florida. This role is unlike a typical corporate Executive Assistant position: it blends executive support, personal assistance, travel management, household coordination, real estate administration, project oversight, and daily operational tasks. The incumbent must demonstrate exceptional adaptability, quick responsiveness, and a personal commitment to the principal's success. The entrepreneur’s schedule is highly variable, favoring candidates comfortable with fluid and evolving responsibilities rather than fixed 9-to-5 routines.

The position requires in-person presence in both Greater Boston and South Florida locations throughout the year for extended periods as needed.

Key Responsibilities

• Efficiently manage complex, shifting calendars and scheduling demands.
• Arrange and coordinate domestic and international trips, often with limited notice.
• Compose and oversee executive correspondence and formal communications.
• Monitor project timelines, priorities, and ensure thorough follow-up.
• Liaise with vendors, contractors, service providers, and handle personal logistics.
• Provide support in real estate matters, household management, administrative tasks, and daily operations.

Ideal Experience

• Previous experience supporting founders, entrepreneurs, company executives, or investors.
• Familiarity working with high net worth individuals (HNWI).

Qualifications and Personal Attributes

• Strong organizational skills with meticulous attention to detail.
• Highly responsive, dependable, and able to maintain confidentiality.
• Professional demeanor combined with discretion and trustworthiness.
• Proactive mindset, anticipating needs before they evolve into challenges.
• Result-oriented focusing on meaningful outcomes beyond task completion.
• Comfortable managing intertwined business and personal responsibilities.
• Ability to maintain close alignment with the principal's priorities and adapt fluidly to changes.