Chief of Staff

About the Organization

We are a high-caliber, membership-based leadership organization serving accomplished executives and business leaders. The organization is focused on creating meaningful connections, high-value experiences, and opportunities for members to grow personally and professionally through curated programming, peer engagement, and community-building.

We are seeking a highly organized, strategic, and relationship-driven Chief of Staff to serve as a key partner to executive leadership and help drive the organization’s priorities across operations, member engagement, events, communications, and strategic initiatives.

Position Overview

The Chief of Staff will act as a strategic and operational partner to leadership, helping translate vision into execution across the organization. This person will play a central role in supporting leadership decision-making, driving cross-functional priorities, maintaining organizational alignment, and ensuring a best-in-class member experience.

This role is ideal for someone who is equally comfortable operating at a strategic level and executing against important day-to-day priorities. The right candidate is proactive, polished, highly organized, and able to build credibility with senior executives and other high-level stakeholders.

Key Responsibilities

Strategic Leadership & Execution

• Partner closely with organizational leadership to develop and execute strategic priorities, with a focus on growth, engagement, retention, and operational excellence
• Help translate leadership vision into actionable plans, timelines, and measurable outcomes
• Monitor key initiatives, track progress, and ensure follow-through across stakeholders
• Analyze engagement data, member feedback, and organizational trends to inform recommendations and decision-making
• Identify opportunities to improve systems, processes, and the overall member experience

Leadership & Board Support

• Serve as a trusted thought partner and operational resource to executive leadership
• Support leadership meetings by helping shape agendas, prepare materials, track action items, and ensure accountability on priorities
• Facilitate communication and alignment among leadership, committees, and broader stakeholder groups
• Help maintain continuity during leadership transitions by preserving institutional knowledge and documenting best practices

Member Experience & Community Engagement

• Oversee the planning and execution of high-impact events, experiences, and engagement initiatives throughout the year
• Ensure a seamless member journey from onboarding through ongoing participation and retention
• Track participation and engagement trends and proactively recommend enhancements to deepen involvement
• Support initiatives that strengthen the value proposition of the organization and elevate the member experience

Operations & Communications

• Oversee core organizational operations, including communications, systems, records, and workflow coordination
• Ensure timely, clear, and consistent communication across email, digital platforms, and member-facing channels
• Serve as a liaison across internal leadership and external stakeholders to ensure alignment and execution
• Maintain organizational documents, systems, and processes with a high degree of accuracy and discretion

Financial & Administrative Oversight

• Assist with budget tracking, payments, dues or revenue oversight, and financial reporting
• Partner with leadership on budgeting, forecasting, and operational planning
• Help ensure resources are allocated effectively to support organizational priorities and events
• Support contract coordination, vendor oversight, and administrative execution tied to major initiatives

Qualifications

5 years of experience in chief of staff, operations, executive support, program management, membership leadership, or a similar strategic support role

• Strong experience partnering with senior executives or high-level stakeholders
• Proven ability to manage multiple priorities, drive execution, and operate effectively in a fast-paced environment
• Excellent communication, project management, and organizational skills
• Strong judgment, discretion, and ability to manage confidential matters professionally
• Experience in membership organizations, nonprofits, associations, private communities, or relationship-driven businesses is strongly preferred

Ideal Candidate Profile

• Strategic, proactive, and highly resourceful
• Comfortable working with senior executives and influential stakeholders
• Strong executor who can move fluidly between high-level planning and detailed implementation
• Naturally organized, detail-oriented, and calm under pressure
• Relationship-builder with strong interpersonal skills and professional presence
• Motivated by mission, community, and creating exceptional experiences

Additional Requirements

• Based in or near Miami, with the ability to work in a hybrid environment
• Available for occasional evening or weekend events
• Comfortable working independently with a high level of ownership and accountability
• Open to limited travel as needed