Senior Executive Assistant / Personal Chief of Staff

Position Overview

An accomplished entrepreneur and investor located in Boca Raton is seeking a highly capable Senior Executive Assistant / Personal Chief of Staff to deliver comprehensive support across various business ventures, investments, and personal affairs. This role transcends traditional administrative duties and demands exceptional organization, discretion, resourcefulness, and the ability to bring structure to a dynamic, fast-paced environment.

Key Responsibilities

• Oversee calendar management, travel arrangements, correspondence, and meeting coordination
• Monitor deadlines, commitments, and ensure timely follow-up
• Maintain and organize business, legal, investor, and financial documentation
• Liaise effectively with attorneys, accountants, investors, vendors, and business partners
• Manage invoice reconciliation, expense tracking, payments, and credit card activities
• Draft correspondence, prepare summaries and briefing documents
• Assist with specific personal and family-related matters
• Develop and implement practical systems to organize files, projects, and priorities
• Handle confidential information with utmost discretion
• Leverage modern productivity tools and AI technologies to enhance efficiency

Candidate Qualifications

• Minimum of seven years supporting founders, CEOs, entrepreneurs, investors, or high-net-worth individuals
• Strong organizational capabilities coupled with excellent written communication skills
• Experience managing sensitive business and personal affairs
• Proficiency with expenses, financial documentation, contracts, or corporate paperwork
• Demonstrates sound judgment and diligent follow-up
• Ability to work autonomously within an entrepreneurial setting
• Availability to work primarily onsite in Boca Raton

Preferred Experience

Background in family offices, investment firms, legal agencies, accounting, healthcare companies, or entrepreneurial enterprises would be advantageous.

Additional Information

This is a trusted, long-term role ideal for someone who values ownership, problem-solving, and supporting a principal in managing a multifaceted professional and personal life.