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Chief of Staff (Orlando)
Chief of Staff (Orlando)Freedom Family Investments • Orlando, FL, United States
Chief of Staff (Orlando)

Chief of Staff (Orlando)

Freedom Family Investments • Orlando, FL, United States
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Role Summary

As a Chief of Staff, you will serve as a strategic partner to the CEO, amplifying impact by ensuring seamless execution of high-priority initiatives. This role is ideal for a seasoned professional adept at navigating fast-paced, entrepreneurial environments, managing complex projects, and leading cross-functional teams. Your primary focus will be to enable the CEO to concentrate on her core priorities : speaking engagements, networking with influencers and strategic partners, content creation, and financial strategy.

Key Responsibilities

Strategic & Executive Support

  • Act as a strategic advisor and thought partner to the CEO, anticipating needs, identifying opportunities, and providing insights to drive organizational growth.
  • Prepare briefing materials, executive summaries, and reports that distill complex information into actionable insights for decision-making.
  • Lead and facilitate high-level meetings, ensuring follow-up on decisions, action items, and accountability.
  • Serve as the CEOs liaison to leadership and department heads, fostering alignment, transparency, and collaboration.
  • Oversee review of critical operational, legal, and financial materials before presentation to the CEO, flagging issues and ensuring accuracy.

Calendar, Travel, and Content Coordination

  • Oversee and prioritize the CEOs calendar, ensuring alignment with strategic goals and high-impact initiatives.
  • Coordinate logistics for speaking engagements, networking events, and company visits, including booking photographers, videographers, and other resources to support content creation.
  • Manage travel arrangements efficiently, optimizing schedules for maximum productivity and strategic value.
  • Support the CEOs content strategy by coordinating with marketing, communications, and creative teams to produce high-impact materials.
  • Attend events with the CEO in person, providing hands-on support and ensuring seamless execution; must be willing to travel as needed.

    • Project & Team Operations

  • Lead the execution of company-wide initiatives, ensuring cross-functional teams meet objectives and deadlines.
  • Manage complex projects from conception through completion, tracking progress, risks, and blockers, and reporting status to the CEO.
  • Evaluate operational processes, identify inefficiencies, and implement improvements to optimize productivity and outcomes.
  • Drive continuous improvement initiatives across the organization using data, analytics, and feedback.
  • Oversee company-wide project management systems and dashboards to ensure executive visibility into key priorities and progress.

    • Talent & Leadership Support

  • Lead the hiring, onboarding, and mentoring of key leadership roles, including a Controller / CFO, ensuring alignment with business needs and cultural fit.
  • Support leadership development programs, fostering accountability, collaboration, and professional growth across teams.
  • Represent the CEO in meetings and events when appropriate, maintaining professionalism and authority in her absence.

    • Required Qualifications

  • Minimum 5+ years in Chief of Staff, Strategic Operations, or senior executive roles supporting C-suite leaders, preferably in high-growth, entrepreneurial, or fast-paced environments.
  • Proven ability to think and act strategically, translating vision into actionable initiatives that drive organizational impact.
  • Demonstrated experience managing complex, cross-functional projects from inception to completion with measurable outcomes.
  • Comfortable reviewing financial statements, budgets, and dashboards; able to identify risks, recommend solutions, and support strategic decision-making.
  • Exceptional written, verbal, and presentation skills; capable of drafting communications, proposals, and reports on behalf of the CEO and influencing stakeholders at all levels.
  • Skilled at leading, coaching, and motivating teams, fostering collaboration and accountability across departments.
  • Adept at managing internal and external relationships, including investors, partners, and senior leadership, with professionalism and discretion.
  • Experienced in leading high-level hiring processes for executive roles, ensuring alignment with business needs and culture.
  • Demonstrated ability to identify issues proactively, prioritize effectively, and make decisions with limited guidance.
  • Comfortable leveraging productivity, project management, and communication tools to optimize workflows and reporting.
  • Thrives in ambiguity and fast-changing environments while maintaining focus on critical priorities.

    • Why This Role Matters

    The CEOs top priorities are :

  • Speaking on stages and podcasts
  • Networking with influencers and strategic partners
  • Content creation & money mastery

    • Your mission is to create the space and structure that allows her to focus entirely on those areas, knowing that operations, communication, and team execution are under control.

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    Chief Of Staff • Orlando, FL, United States

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