Technical Support Specialist

Position: Employee Benefits Technical Support Specialist
Employee Benefits Technical Support Specialist (Contract)

REQUIREMENTS

Remote | 25-35 Hours/Week with Predictable Daytime Schedule

Candidates must be located in the Eastern or Central Time Zone

Requires this to be your primary professional engagement

Help employees understand their benefits, get answers, and make better use of the coverage and resources available to them.

Paragon Risk Advisers is a boutique employee-benefits consulting firm serving a variety of employer types and sizes. You'll work closely with client leadership teams and often serve as their dedicated benefits department.

We’re seeking an experienced benefits professional who enjoys investigating problems, working through the details, and taking ownership of the resolution. You should be equally comfortable helping an employee resolve a coverage issue, identifying an enrollment discrepancy, and explaining a benefit clearly.

Approximately 80% of this engagement focuses on benefits technical support, employee advocacy, and administration, with 20% devoted to using data, AI, and digital tools to increase employee engagement, strengthen benefits awareness, and improve service delivery.

THE ENGAGEMENT AND COMMITMENT

This is an individual independent-contractor opportunity with anticipated capacity of 25–35 hours per week.

Candidates must be located in the Eastern or Central Time Zone and commit to a predictable, recurring schedule during traditional daytime business hours, aligned with Paragon’s Eastern Time business day. Regular working days and hours will be agreed upon in advance so employees, clients, carriers, and Paragon leadership know when you are available.

This work requires daytime participation in employee support, carrier issue resolution, and scheduled meetings. Work performed primarily during evenings, nights, or weekends will not meet the needs of this engagement.

We are seeking someone who intends to make Paragon their primary professional engagement and can consistently provide the attention, responsiveness, and follow-through our clients need.

Other professional activities must not compete with Paragon’s benefits services, create conflicts of interest, or interfere with the agreed schedule and deliverables. This opportunity is best suited to someone seeking a substantial, ongoing engagement rather than supplemental work around another primary job.

The work is remote, with independence in how you organize and complete assignments within the agreed service schedule.

BENEFITS TECHNICAL SUPPORT AND ADMINISTRATION — APPROXIMATELY 80%

Employee advocacy and issue resolution

• Help employees navigate claims questions, coverage issues, , benefit transitions, and carrier resources.
• Investigate problems with carriers, administrators, and client contacts; track each issue through resolution.
• Use plan documents and verified source materials to explain benefits accurately and recognize when an issue needs escalation.
• Maintain clear records of questions, actions, outstanding items, and resolutions.

Eligibility, enrollment, and data accuracy

• Coordinate recurring eligibility updates and support new hires, qualifying life events, and terminations.
• Compare HRIS, benefits administration, and carrier records to identify missing enrollments, incorrect coverage, and effective-date discrepancies.
• Extract, organize, and validate census and enrollment information using Excel and relevant systems.
• Support benefits invoice review and reconciliation by investigating discrepancies and coordinating corrections.

Benefits communications and client support

• Prepare clear employee communications, benefit summaries, FAQs, and open-enrollment materials.
• Verify plan details, contribution information, dates, and links against approved sources.
• Support virtual employee…