Chief of Staff

POSITION OVERVIEWA trusted, highly capable right-hand to two Principals leading a fourth-generation entrepreneurial family enterprise with diversified business interests. The Chief of Staff sits at the center of Principal priorities, organizational execution, and team effectiveness. Ensuring that the Principals' attention is directed where it matters most and that their initiatives move forward with speed and precision.This family operates with an entrepreneurial mindset (decisive, ambitious, and always forward moving). The Chief of Staff must match that pace. This is not a role for someone who waits to be directed or presents problems without answers. The right candidate arrives prepared, leads with a clear recommendation, troubleshoots before escalating, and approaches every challenge with a genuine "how can I help?" orientation. KEY RESPONSIBILITIESPrincipal Support — Core Function•     Serve as the primary point of coordination for two Principals across different states, managing competing priorities with precision, calm, and full accountability.•     Anticipate needs before they surface, research, prepare, and position the Principals to make informed decisions quickly and confidently.•     Bring forward well-reasoned recommendations on complex matters; approach every issue with a point of view and a plan.•     Handle confidential correspondence, sensitive communications, and private matters with absolute and unwavering discretion.Staff Support & Organizational Effectiveness•     Serve as a reliable, solutions oriented resource for staff across the organization. Approachable, proactive, and effective.•     Maximize the effectiveness of Executive Assistants and operational staff through clear direction and strong coordination.•     Identify where the team is stretched, unclear, or stuck and resolve it without being asked.•     Facilitate smooth communication and information flow.•     Recruiting responsibilities may be required based on business needs.Project & Initiative Management•     Own cross functional projects and priority initiatives on behalf of the Principals from inception through successful completion.•     Hold internal teams and external partners accountable to timelines, standards, and outcomes.•     Surface issues early, diagnose them accurately, and present a clear path forward.•     Maintain the Family Office Event Calendar; own the planning and flawless execution of key events and engagements.Communications & Logistics•     Prepare polished briefing documents, presentations, and executive communications on behalf of the Principals.•     Coordinate travel, scheduling, and logistics for the Principals across multiple locations.•     Serve as a trusted and professional liaison between the Principals and internal/external stakeholders.EXPERIENCE•     7+ years in a Chief of Staff, executive operations, or senior principal support role within a demanding, high standards environment.•     Experience supporting entrepreneurial leadership, multi-entity holding companies, or family enterprise principals is strongly preferred.•     Background working directly with C-suite executives or founders in a fast-moving, confidential setting.•     Single Family Office (SFO) or private family enterprise experience is a differentiator.•     Five-star hospitality, luxury brand, or high-touch service background is a plus.REQUIRED SKILLS & TRAITS•     Confident and autonomous — takes ownership, makes decisions, and delivers results without hand-holding.•     Exceptional troubleshooter — identifies root causes quickly and executes solutions, not workarounds.•     "How can I help?" orientation — proactively seeks out where value can be added and closes the gap.•     Brings recommendations to the table, not menus of options — has a point of view and can defend it.•     Entrepreneurial sensibility — energized by a dynamic, fast-moving environment and comfortable navigating ambiguity.•     Sharp critical thinker; synthesizes complex information quickly and acts with sound, independent judgment.•     Technologically savvy — fluent in modern productivity tools, project management platforms, and digital workflows.•     Absolute discretion and confidentiality — trusted with the most sensitive business and personal matters.•     Outstanding written and verbal communication skills; polished across all formats and audiences.•     Proven ability to manage multiple high-priority projects simultaneously without losing detail.•     Calm, composed, and solutions-focused under pressure — never reactive.•     Advanced proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook).•     Roll up your-sleeves work ethic; positive, no drama disposition with high emotional intelligence.LOCATIONIdeally based in Palm Beach Gardens, FL. Open to candidates located anywhere in the Eastern Standard Time Zone with willingness to travel regularly to the Palm Beach Gardens office and other Principal locations as needed.EDUCATION•     Bachelor's degree required; strong academic record expected. MBA or advanced degree preferred.