Medicare Project Manager

Operations Park Ridge, Illinois


Position at Clear Spring Health

Group1001 is a consumer-centric, technology-driven family of insurance companies on a mission to deliver outstanding value and operational performance by combining financial strength and stability with deep insurance expertise and a can-do culture. Group1001’s culture emphasizes the importance of collaboration, communication, core business focus, risk management, and striving for outcomes. This goal extends to how we hire and onboard our most valuable assets – our employees.

Company Overview:

Clear Spring Health is part of Group One Thousand One (“Group1001”), a customer-centric insurance group whose mission is to make insurance more useful, intuitive and accessible so that everyone feels empowered to achieve financial security. Clear Spring Health is dedicated to helping seniors protect their health and well-being by providing Medicare Advantage plans in select counties of Colorado, Illinois, North Carolina, and Virginia, plus Georgia and South Carolina and offers Medicare Prescription Drug Plans in 42 states plus DC. 

Group 1001, and its affiliated companies, is strongly committed to providing a supportive work environment where employee differences are valued. Diversity is an essential ingredient in making Group 1001 a welcoming place to work and is fundamental in building a high-performance team. Diversity embodies all the differences that make us unique individuals.  All employees share the responsibility for maintaining a workplace culture of dignity, respect, understanding and appreciation of individual and group differences.

Job Summary:

Support Sales, Sales Operations and Marketing by managing various system and non-system project implementations (e.g., annual open enrollment readiness) to ensure projects are delivered on-time, within scope and on budget.

Main Accountabilities:

  • Manage multiple new system implementations and end-to-end readiness initiatives of varying sizes and scopes
  • Determine and define project scope, objectives and needed resources
  • Prepare budget based on scope of work and resource requirements and track costs
  • Develop and manage a detailed project schedule and work plan including identifying integration points and project dependencies
  • Create and maintain comprehensive supporting project documentation
  • Detect risks and issues as well as remediation efforts and escalation processes
  • Provide project updates on a consistent basis to various stakeholders about strategy, adjustments, and progress
  • Identify measures to ensure short-term and long-term project objectives have been met or exceeded


  • Bachelor's degree in organizational management, business, information technology or project management. PMP (Six Sigma certified; purple or higher) preferred but not required.
  • 5 years of project management experience including leading system integrations.
  • Strong experience with project management software tools, methodologies and best practices.
  • Knowledge of sales operations, Customer Response Management (CRM) and enrollment platforms.
  • 5+ years of Health Insurance experience.
  • Experience in Medicare Advantage, Medicare Part D or Medicare Supplement is preferred but not required.
  • Exceptional written and verbal communication skills.
  • Strong analytical skills.
  • Strong interpersonal skills and an ability to build relationships internally and externally.
  • Be driven and ambitious with a strong desire to exceed expectation.
  • Highly organized with strong attention to detail.