Medicare Sales Operations Analyst - Remote

Insight Global is seeking a detailoriented, executionfocused professional to support a large Medicare Sales Operations organization within the Digital Readiness & Implementation function. This role sits at the intersection of data, operations, and partner enablement, playing a key role in ensuring vendors, platforms, and digital experiences are operationally ready-especially during the Annual Enrollment Period (AEP).
This opportunity is ideal for someone who thrives in fastpaced, highly regulated environments, is comfortable working through data ambiguity, and takes ownership of driving work forward across multiple internal teams and external partners.

Drive execution of Digital Readiness initiatives, ensuring vendors and partners meet critical AEP timelines and readiness requirements
Act as a central point of coordination between external vendors and internal operational, technical, and business teams
Manage and validate operational data, including reports, file transfers, reconciliations, and data quality checks
Track implementation milestones, risks, dependencies, and deliverables across multiple workstreams
Create, submit, and manage JIRA tickets, ensuring issues are documented, prioritized, and driven through resolution
Support AEP testing efforts, including validation of digital sites, benefit configurations, and readiness checkpoints
Perform analytical reviews to identify trends, gaps, or potential operational risks
Document decisions, action items, and outcomes to support operational transparency and compliance
Ensure operational accuracy and adherence to regulatory and compliance standards-
- Support Health Risk Assessment (HRA) completion and paymentrelated inquiries
- Research, validate, and reconcile HRA data across systems and reports
- Partner with HRA technology and operations teams to resolve data or platform issues
- Communicate system outages, defects, or platform disruptions to stakeholders
- Develop a working understanding of HRA data flows and dependencies to support issue resolution.


Looking for an hourly range of $35-45/hr

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to View email address on click.appcast.io learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy:


Required Skills & Experience
• Healthcare experience, preferably Medicare or health insurance
• Experience with operational data and reporting
• Strong coordination and communication skills
• High attention to detail
• Ability to learn new systems quickly
• Self-directed and dependable


Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.