Chief of Staff (Orlando) Job at Freedom Family Investments, Orlando, FL

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  • Freedom Family Investments
  • Orlando, FL

Job Description

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:

  1. Speaking on stages and podcasts
  2. Networking with influencers and strategic partners
  3. 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.

Job Tags

Part time,

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