About the Role

FreedomCare is growing quickly, and we are looking for a highly motivated, resourceful Chief of Staff to support our senior leadership team. The Chief of Staff will also collaborate with leaders across multiple business functions.

This is more than a traditional administrative role. You will be a trusted partner who is fully engaged in the work of the leaders and teams you support; present, prepared, curious, and invested in FreedomCare’s success. You will help senior leaders manage their time, communicate effectively, prepare for important meetings, and advance critical priorities.

The ideal candidate is sharp, curious, technologically savvy, and eager to learn. You anticipate needs, bring structure to fast-moving situations, and are comfortable taking initiative when the path forward is not fully defined.

Responsibilities & Scope

Proactively manage complex calendars, resolve scheduling conflicts, and ensure leaders’ time reflects their most important priorities.
Coordinate virtual and in-person meetings, including agendas, materials, logistics, technology, and follow-up.
Help plan leadership meetings, operating reviews, off-sites, and other key events.
Develop and refine executive-ready presentations using PowerPoint and Google Slides.
Draft, edit, and format internal and external communications, reports, meeting materials, and other executive documents.
Track decisions, action items, deadlines, and follow-ups to help maintain momentum across priorities.
Arrange travel, prepare detailed itineraries, and manage expense reports.
Prepare leaders for meetings by gathering relevant context, organizing materials, and anticipating questions or needs.
Partner with teams across the organization to coordinate information and support cross-functional initiatives.
Identify gaps, inefficiencies, or recurring challenges and create practical solutions.
Learn and use new technologies, including productivity and AI-enabled tools, to improve workflows and increase efficiency.
Support special projects, both independently and collaboratively based on evolving business needs.
Handle confidential and sensitive information with sound judgment and discretion.

Education & Experience

3+ years of experience supporting multiple senior executives in a complex, fast-paced environment.
Demonstrated ability to manage competing priorities and concurrent assignments with accuracy, urgency, and strong follow-through.
Advanced presentation development skills using PowerPoint and/or Google Slides.
Proficiency with Microsoft Office or Google Workspace, including spreadsheets and reporting tools.
Experience using AI-enabled productivity tools in a professional environment to improve efficiency and work quality.
Strong written and verbal communication skills, including the ability to communicate effectively with executives and stakeholders at all levels.
Exceptional organizational, planning, and time-management abilities.
Excellent attention to detail and the ability to connect day-to-day activities to broader business objectives.
Strong judgment, professionalism, and discretion when handling confidential information.
Comfort adopting new technology and learning unfamiliar systems quickly.
A proactive, solutions-oriented mindset; you notice what needs to be done and take ownership.
A strong sense of ownership and consistent follow-through from initial request through completion.
Adaptability and composure in an environment where priorities can change quickly.
A collaborative, positive attitude and willingness to contribute wherever needed.

Nice-to-Haves

Experience supporting operational leaders, including executives responsible for multiple markets, regions, or business functions.
Experience working in a rapidly growing company, startup, or similarly dynamic environment.
Familiarity with project management.

Why Work at FreedomCare?

We are here for you and committed to providing a best-in-class employee experience. We offer competitive compensation, medical benefits, retirement plans, wellness programs, fun company events, and ongoing learning opportunities to grow your career.

Harvard Business School - Elevate Your Leadership

Chief of Staff