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Chief of Staff

RLDatix
Chicago, IL
| Executive | Chicago | Hybrid

RLDatix (RLD) is on a mission to help raise the standard of care…everywhere. Trusted by over 10,000 healthcare organizations around the world, our solutions help improve health and care. Our applications ensure that patients receive the best and safest care while supporting the providers who deliver it.

Joining TeamRLD means being part of a global effort of over 2,000 team members in making a difference in healthcare…every day.

We’re searching for a Chicago-based Chief of Staff to join our Office of the CEO team, so that we can drive strategic alignment, operational efficiency, and executional excellence across the business.

The Chief of Staff will act as a high-impact partner to our CEO, ensuring priorities are executed, communications flow seamlessly, and mission-critical initiatives stay on track. This is a role for someone who is just as comfortable building strategic frameworks as they are rolling up their sleeves and handling logistics behind the scenes.

How You’ll Spend Your Time

  • Facilitate strategic planning processes (annual, quarterly) to drive OKRs, track execution, and ensure alignment across business units
  • Project manage key initiatives such as RLD 2030, board meeting preparation, and core week planning
  • Create and manage company-wide scorecards and operating cadences to optimize performance and communication
  • Lead and streamline internal communications, executive memos, and content preparation for board and partner meetings
  • Conduct deep-dive analysis to support high-level decision making with synthesized insights and recommendations

What Kind of Things We’re Most Interested in You Having

  • Experience in consulting, business operations, investment banking, or a Chief of Staff role—ideally in a SaaS or high-growth company
  • Proven success in driving cross-functional initiatives and managing multiple executive-level priorities in a fast-paced environment
  • In-depth knowledge of how to build scalable processes, facilitate executive-level communications, and manage strategic planning cycles
  • Ability to commute to Chicago several times a week and be in-office during Core Weeks, Board Meetings, or critical planning sessions
  • Sincere interest in healthcare, innovation, and executive leadership operations
  • A knack for working collaboratively across departments and independently executing on high-priority, complex projects with precision

By enabling flexibility in how we work and prioritizing employee wellness, we empower our team to do and be their best. Our benefits package includes health, dental, vision, life, disability insurance, 401K, paid time off, and paid holidays.

RLDatix is an equal opportunity employer, and our employment decisions are made without regard to race, color, religion, age, gender, national origin, disability, handicap, marital status or any other status or condition protected by Federal and/or State laws.

As part of RLDatix’s commitment to the inclusion of all qualified individuals, we ensure that persons with disabilities are provided reasonable accommodation in the job application and interview process. If reasonable accommodation is needed to participate in either step, please don’t hesitate to send a note to [email protected].

Salary offers are based on a wide range of factors including location, relevant skills, training, experience, education, and, where applicable, licensure or certifications obtained. Market and organizational factors are also taken into consideration.

Key Responsibilities

  • Strategic Planning & Execution Support:
  • Facilitate the annual and quarterly strategic planning processes, ensuring alignment across departments and clear articulation of objectives and key results (Rocks).
  • Project Manage the RLD 2030 strategic planning and review process
  • Maintain the Operating Cadence of the business ensuring efficiency, clarity, and optimization. This includes management of the Company Corporate Calendar
  • Monitor the progress of strategic initiatives, identifying potential roadblocks and proactively working with relevant teams to ensure timely execution.
  • Prepare comprehensive reports and presentations for executive leadership, board meetings, and external stakeholders, distilling complex information into clear, actionable insights.
  • Design, preparation and oversight of coordination of our Board Meetings and Key Partner meetings
  • Operational Efficiency & Process Optimization:
  • Create, facilitate, and manage monthly and quarterly scorecard process across all functions, regions, and business segments.
  • Identify opportunities to streamline internal processes, improve cross-functional collaboration, and enhance overall organizational efficiency.
  • Work with Executive Leadership Circle to design and implement scalable operational frameworks and best practices to support company growth.
  • Manage critical projects from inception to completion, ensuring meticulous attention to detail and adherence to timelines.
  • Identifies opportunities to streamline delivery workflows by eliminating redundancies and applying continuous improvement principles with disciplined execution focus across portfolios.
  • Communication & Information Flow:
  • Act as a central point of contact and communication hub between the CEO and various internal and external stakeholders.
  • Prepare executive communications, presentations, and internal memos, ensuring clarity, conciseness, and alignment with the executive's voice and vision.
  • Manage the executive's priorities, meeting agendas, and follow-up actions, ensuring effective time management and decision-making in partnership with the Executive Assistant.
  • Analytical Insight & Problem Solving:
  • Conduct deep-dive analysis on various business challenges, market trends, and operational data to provide data-backed recommendations.
  • Identify critical issues and proactively propose solutions, often involving complex data sets and cross-functional input.
  • Support decision-making by providing timely, accurate, and relevant information.
  • Synthesis complex project information from multiple sources, creating comprehensive portfolio insights and strategic reports that support decision-making for steering committees and senior leadership audiences.
  • Extracts meaningful insights from complex delivery datasets using analytical techniques to uncover patterns and trends that inform portfolio decisions and performance.
  • Special Projects & Initiatives:
  • Lead and manage ad-hoc strategic projects as assigned by the executive, which may span across different functional and regional teams.
  • Represent the executive in various internal and external meetings, committees, or events as needed.

Qualifications

Required:

  • Bachelor’s degree in business administration, Finance, Economics, Healthcare Management, or a related analytical field.
  • 5+ years of experience in a highly analytical role such as consulting, investment banking, business operations, project management, or a previous Chief of Staff role.
  • Proven experience in a fast-paced, high-growth environment, ideally within the SaaS sector.
  • Demonstrated analytical prowess: Ability to quickly grasp complex concepts, synthesize information, and draw insightful conclusions from data.
  • Exceptional process orientation and attention to detail: Meticulous in planning, execution, and follow-up, ensuring nothing falls through the cracks.
  • Strong project management skills with a track record of successfully driving initiatives to completion.
  • Outstanding communication skills (written and verbal), with the ability to articulate complex ideas clearly and concisely to diverse audiences.
  • Very proficient in data analysis tools (e.g., Excel, SQL, BI tools) and presentation software (e.g., PowerPoint, Tableau, Google Slides).
  • Ability to work independently and collaboratively in a dynamic, rapidly changing environment.

Preferred

  • Master's degree (MBA or equivalent).
  • Experience within the healthcare industry or healthcare technology.
  • Experience working directly with C-level executives within Private Equity backed businesses.
  • Ideally based in Chicago

Additional Notes

Board Meetings & Core Weeks

Here is a structured list of tasks related to managing Board Meetings, Core Weeks, and Pre-Board Meetings:

Internal SLT Core Weeks

  • Working with August or Paul S to build out the agenda for the week
  • Send out all the meeting invites after confirming the attendees
  • Send out the joining instructions (where to stay, start times, logistics, agenda)
  • Book the social events (partner with Kate Z in NAM and Sabina in UK). Often arranging for payment of the social events
  • Manage the drinks and refreshments (breakfasts / lunches etc)
  • Set up the meeting spaces
  • Chase up the content for each session from the session owners and distribute
  • Ad hoc requests, examples include ordering Books for the SLT like Reset, or Badges for the event

Board Meetings

Board meetings are quarterly, mid-June, mid-September, mid-December and mid-March.

  • Agree agenda with CEO and Investors
  • Agree location and dates (rolling 12 months in advance) of Boarding with CEO and investors
  • Coordinate internal content with relevant ELC member – chase up content, review content, format content, pre reads with CEO
  • [CEO normally distributes the content c.48 hours in advance]
  • Ensure that printing and binding is completed before the meeting
  • Ensure Board dinner is coordinated
  • In the Board meeting ensure AV/VC equipment works, present the slides, move the slides.
  • Record the minutes for the Board meeting.

Pre Board Meetings

Board meetings are quarterly, mid-June, mid-September, mid-December and mid-March.

  • Send out the invitations to the FA/TA working groups
  • Agree agenda with CEO
  • Coordinate internal content with relevant ELC member – chase up content, review content, format content, pre reads with CEO
  • Distribute the content to attendees at least 48 hours in advance
  • Ensure that printing and binding is completed before the meeting
  • Ensure room and refreshments are booked
  • In the meeting ensure AV/VC equipment works, present the slides, move the slides.
  • Record the minutes and actions of the meetings
Posted 2025-08-31

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