Onsite Role in Chicago, IL

As the Executive Assistant to the Director, Office of the CEO, you will serve as the operational backbone of one of R1's most visible and high-impact functions. This role creates the runway that allows the Office of the CEO to operate at full strategic altitude — by owning scheduling, travel, and organizational systems with precision, discretion, and without needing to be managed.

Every day, the Executive Assistant manages the logistics, coordination, and administrative systems that keep the CEO office running at the pace and quality of a PE-backed, enterprise-scale healthcare technology company. This is not a traditional administrative role — it is a high-trust position that demands professionalism, executive-level polish, and an ownership mentality from day one. To thrive in this role, you are proactive, not reactive. You anticipate what's needed before being asked, execute without handholding, and understand the difference between what's yours to run and what routes to your manager first. You are calm under pressure, discreet by nature, and take genuine pride in making complex operations look effortless.

Here’s what you will experience working as an Executive Assistant:

Calendar & Executive Scheduling

• Own and manage the CEO/Directors calendars end-to-end: scheduling, rescheduling, conflict management, and reminders
• Learn the scheduling hierarchy and protect focus time and deep work blocks proactively
• Coordinate scheduling with ELT members, external partners, and vendors on the Director's behalf
• Send prep reminders with relevant materials 48 hours ahead of key meetings
• Track and follow up on action items from meetings, close the loop with owners
• Support CEO-level meeting scheduling logistics as directed, Director remains the primary contact

Travel & Logistics

• Book and manage all travel for the Director: flights, hotels, ground transport, and full itineraries
• Prepare detailed travel briefings with context, attendees, logistics, and contingency plans
• Support travel logistics for CEO and ELT events as directed
• Manage expense reporting and reconciliation in a timely and accurate manner

Administrative Organization

• Maintain and organize the Director's shared drive, filing systems, and document libraries
• Own the operational tracker for active workstreams: deadlines, action items, and open loops
• Draft routine correspondence and communications for Director's review and send
• Manage incoming scheduling requests and inquiries — route to Director for all decisions
• Coordinate logistics for leadership forums, executive offsites, and team events as directed

Office Support

• Support Board meeting logistics coordination as directed, Director leads all Board-facing communication
• Assist with onboarding logistics for new hires as needed
• Help coordinate EA Excellence Series session logistics for the 14-person Executive Business Partner team
• Manage administrative budget tracking, invoice processing, and expense management for the Office of the CEO

Required Skills:

• Minimum of three years of administrative experience.
• Must have excellent planning, time management, and organizational skills.
• Excellent verbal and written business communication skills.
• Ability to succeed in an ever-changing and fast-paced environment.
• Ability to effectively manage multiple, competing priorities under a given timeline.
• Ability to show considerable discretion regarding sensitive and/or confidential information.
• Strong proficiency in MS Outlook, Word, Excel and PowerPoint.

For this US-based position, the base pay range is $85,825.25 - $107,281.56 per year . Individual pay is determined by role, level, location, job-related skills, experience, and relevant education or training.

This job is eligible to participate in our annual bonus plan at a target of 5.00%