Executive Assistant

R1 is the leading provider of technology-driven solutions that transform the patient experience and financial performance of hospitals, health systems and medical groups. We are the one company that combines the deep expertise of a global workforce of revenue cycle professionals with the industry’s most advanced technology platform, encompassing sophisticated analytics, AI, intelligent automation, and workflow orchestration.

Onsite Role in Chicago, IL

As our Executive Assistant, you will support our CEO and serve as the primary liaison to the Board of Directors, acting as a seamless connection between the CEO, Executive Leadership Team, and Board. In this full-time, in-office role, you will manage complex administrative responsibilities with discretion and integrity, protect the CEO’s time and focus, anticipate needs, navigate competing priorities, make sound independent decisions, and represent the CEO’s voice in select communications. This role is ideal for a proactive, detail-oriented communicator who thrives in a dynamic environment and offers a unique opportunity to gain visibility into how the business operates while playing a direct role in keeping it moving forward.

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

Executive Support

• Provide high-level administrative support to the CEO, including complex calendar management, scheduling, domestic and international travel (flights, accommodations, detailed itineraries), and expense reporting.

• Prepare and organize materials for meetings, presentations, and correspondence.

• Assist in prioritizing tasks and follow up on action items through to completion.

• Handle confidential and sensitive information — strategic plans, financial reports, legal documents, and HR matters — with absolute discretion and integrity.

• Support adherence to corporate governance processes, deadlines, and best practices.

• Screen calls, emails, and inquiries, and route them appropriately.

• Keep the CEO informed on the progress, risks, and key developments of high-priority initiatives.

• Co-Lead the Executive Assistant team with EA to CFO.

• Support select personal requests (e.g., personal travel) as needed.

• This role operates with a high degree of autonomy; you will be expected to handle most scheduling and communication decisions independently and work closely with CEO on decisions where appropriate. Only escalating when needed.

Board Liaison

• Coordinate all logistics for Board meetings with EA partner — scheduling, agendas, materials distribution, and setup of meeting rooms or virtual platforms and board portals.

• Support the CEO’s communication with Board members, ensuring smooth interaction and collaboration.

Required Skills:

• 5+ years of executive support experience; support at the CEO/C-suite level preferred, including exposure to Board relations and corporate governance.

• Exceptional organizational and time-management skills, with the ability to manage competing demands and prioritize effectively.

• Strong verbal and written communication skills, with the ability to engage executives, Board members, and stakeholders at all levels.

• High proficiency with office technology (Microsoft 365) and project-management tools.

• Comfort and fluency using AI tools to increase output and quality, paired with judgment about appropriate use.

• Ability to work independently and as part of a team while maintaining discretion and professionalism.

• Proven ability to anticipate needs and address them proactively.

• Strong attention to detail, ensuring accuracy and consistency.

• Ability to adapt and thrive in a fast-paced, dynamic environment.

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%

The healthcare system is always evolving — and it’s up to us to use our shared expertise to find new solutions that can keep up. On our growing team you’ll find the opportunity to constantly learn, collaborate across groups and explore new paths for your career.

Our associates are given the chance to contribute, think boldly and create meaningful work that makes a difference in the communities we serve around the world. We go beyond expectations in everything we do. Not only does that drive custo…