Chief of Staff

Job Summary: We are seeking a highly strategic, exceptionally organized, and deeply trustworthy Chief of Staff to serve as the direct right hand to the CEO of our privately owned, multisite healthcare practice based in Chicago. With a team of approximately 100 employees spanning clinical, operational, and administrative functions, this role sits at the center of our organization’s most critical decisions and day-to-day execution. This position goes well beyond traditional administration. You will serve as the CEO’s proxy in key meetings, directly manage the marketing team, and partner closely with clinical, technical, and operational staff to ensure organizational priorities move forward with speed and precision. The role combines meticulous organizational discipline with a forward-thinking, data-driven mindset—and carries the judgment and discretion required to operate at the executive level in a healthcare environment. Primary Job Duties • Serve as a seamless extension of the CEO—represent the CEO’s voice and directives in critical meetings when needed, and deliver clear, concise takeaways upon return. • Keep the CEO focused and on target with daily priorities, project timelines, and longer-term organizational goals. • Serve as a trusted sounding board for key business decisions, providing thoughtful analysis and perspective in a fast-paced, privately owned environment. • Manage the CEO’s complex schedule, ensuring time is allocated to the highest-impact activities. • Plan, coordinate, and confidently lead internal and external meetings on behalf of the CEO. • Act as the primary gatekeeper and problem solver for all administrative and operational matters flowing from the Office of the CEO. • Collaborate across our team including Executive leadership, clinical staff, the Mobile team, and the Patient Engagement Specialist to ensure seamless cross-functional communication and execution. • Partner with and support the CEO’s Patient Engagement Specialist on clinical priorities, ensuring patient-facing initiatives are properly resourced and executed. • Travel locally throughout the Chicago metro area to practice facilities and external sites as required to support the CEO and organizational needs. • Manage confidential company, personnel, and patient-related information with the utmost discretion; a Confidentiality Agreement (NDA) is required upon hire. • Directly manage and oversee the Marketing team, providing strategic direction, accountability, and support to ensure initiatives are aligned with brand and growth goals. • Serve as the bridge between marketing efforts and the broader clinical and operational priorities of the practice. • Generate, run, and analyze vital business reports to keep executive leadership informed and support data-driven decision-making. • Lead AI integration and workflow optimization efforts and identify opportunities to streamline tasks, automate routine operations, and increase efficiency within the Office of the CEO. • Leverage modern productivity tools to continuously improve how the CEO’s office operates. • Other job-related duties as assigned. Education and Experience Requirements: • Bachelor’s degree in Business Administration, Healthcare Administration, Management, Communications, or a related field is required. • Advanced degree or professional certification (e.g., MHA, MBA) is a plus, particularly with a focus in healthcare or organizational leadership. • Prior experience in a Executive Operations, or senior administrative leadership role, ideally within a healthcare, medical, or similarly complex organizational setting. • Demonstrated ability to manage teams and lead cross-functional collaboration with clinical, technical, and marketing personnel. • Advanced proficiency in Microsoft Office Suite, including Excel (data analysis, reporting), Word, and PowerPoint. • Strong ability to pull, analyze, and present data and business metrics to executive leadership. • Proven track record of implementing AI tools and modern productivity platforms to improve operational workflows. • Experience operating in a fast-paced, privately owned business environment where priorities shift quickly and judgment matters. • Exceptional organizational skills with the ability to manage competing priorities, multitask effectively, and bring structure to a dynamic executive office. • High degree of professionalism and discretion; must be trusted to handle highly sensitive company, personnel, and clinical information. • Strong written and verbal communication skills with the confidence to represent the CEO internally and externally. • Willingness and ability to travel regularly within the Chicago metro area to practice facilities and external sites. • Self-starter with a proactive, solutions-oriented mindset and the instinct to anticipate needs before they arise. • Must be able to pass a background check, drug screen and all onboarding requirements. • Upon acceptance of position, required to sign an NDA & Confidentiality Agreement.