Chief of Staff to Principal

Boca Raton, Florida | On-Site (3–5 Days Per Week)

An accomplished and dynamic Principal based in Boca Raton is seeking a Chief of Staff to serve as her strategic right hand. This individual will play a critical role in protecting the Principal’s time, driving organization and operational excellence, and ensuring the seamless execution of both personal and professional priorities.

This is a unique opportunity to work alongside an exceptionally intelligent, driven, and visionary leader. The environment is fast-paced and outcome-oriented, offering unparalleled proximity to a high-performing Principal and a small, dedicated team.

The ideal candidate is highly organized, proactive, and solutions-oriented, with the ability to anticipate needs, implement systems, and operate with discretion and ownership.

This role requires someone who thrives in a high-performance environment, is comfortable with direct communication, and approaches challenges with creativity, accountability, and resilience.

Key Responsibilities

Strategic Right Hand

• Serve as the Principal’s trusted partner in managing priorities, commitments, and daily operations.

• Protect and optimize the Principal’s time by acting as a gatekeeper to her calendar, communications, and commitments.

• Ensure all meetings, travel, and engagements are purposeful, efficient, and aligned with priorities.

• Anticipate needs and proactively move initiatives forward without requiring constant direction.

Calendar & Time Management

• Maintain deep oversight of the Principal’s schedule, ensuring clarity around time commitments for both the Principal and the broader team.

• Evaluate incoming requests and commitments with discernment, ensuring the Principal’s time is used intentionally.

• Create structure and flow within the day while ensuring the Principal maintains time to recharge and operate at her best.

Operations & Systems

• Bring structure, organization, and operational excellence to the Principal’s life and ecosystem.

• Identify opportunities to streamline workflows, develop systems, and eliminate inefficiencies.

• Maintain organized processes and ensure information, communications, and priorities remain clear and actionable.

Team Leadership & Collaboration

• Work closely with the Executive Assistant and Personal Assistant while maintaining full visibility into their responsibilities.

• Provide leadership, guidance, and support to ensure the team operates cohesively and effectively.

• Foster a culture of ownership, accountability, and continuous improvement.

Property & Logistics Oversight

• Coordinate across the Principal’s residences, including:

  • Boca Raton (primary residence)

  • Miami

  • New York City

  • The Hamptons

• Collaborate with existing property professionals including a Hamptons property manager and New York building superintendent.

• Oversee readiness of properties, particularly Miami, ensuring homes are fully prepared ahead of the Principal’s arrival.

Travel & Lifestyle Management

• Manage and coordinate travel logistics when required.

• Research and secure best-in-class accommodations and experiences aligned with the Principal’s preferences.

• Build and maintain a detailed preference profile to ensure consistency across locations and travel.

Problem Solving & Accountability

• Operate with a solutions-first mindset — “no” is never the final answer.

• When challenges arise, take ownership, address them quickly, and implement systems to prevent recurrence.

• Maintain composure and professionalism in a fast-paced and high-expectation environment.

Ideal Candidate

The ideal candidate is:

• Highly organized, meticulous, and detail-oriented

• Comfortable operating in a fast-paced, high-performance environment

• Proactive and anticipatory, with strong judgment

• Solutions-oriented with strong problem-solving ability

• Emotionally intelligent and able to handle direct communication with professionalism

• A natural leader who can guide and develop those around them

• Tech-savvy and comfortable leveraging digital tools and systems

• Someone who appreciates fashion, aesthetics, and lifestyle environments

• Personally driven to grow both professionally and personally

Additional Details

Location: Boca Raton, Florida
Schedule: On-site 3–5 days per week with a flexible, 24/7 mentality when needed
Travel: Occasional travel required
Team: Collaborative environment alongside a CEO and a dedicated long-term team member

Why This Role

This is an extraordinary opportunity to work closely with an exceptional Principal while helping shape the systems and operations around a dynamic life and business environment.

The right candidate will gain unique exposure, meaningful responsibility, and the opportunity to grow alongside an ambitious and driven leader.