Employee Benefits Support Specialist

Employee Benefits Support Specialist (Contract)

Remote • Eastern or Central Time Zone Required • 25–35 hours per week • Predictable daytime schedule

Help employees get answers, resolve benefits problems, and understand the coverage and resources available to them.

Paragon Risk Advisers is a boutique employee-benefits consulting firm serving employers of varying types and sizes. We work closely with client leadership teams and often serve as their dedicated benefits department.

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

Approximately 80% of this engagement focuses on employee benefits support, advocacy, and administration. The remaining 20% focuses on using AI and digital tools to improve employee education, benefits awareness, engagement, and service delivery.

Location, schedule, and commitment

You must currently reside in the Eastern or Central Time Zone. Mountain and Pacific Time locations are not eligible, even if you are willing to work Eastern Time hours.

This is an individual independent-contractor opportunity requiring approximately 25–35 hours per week on a predictable, recurring daytime schedule aligned with Paragon’s Eastern Time business day.

Regular working days and hours will be agreed upon in advance. Employees, clients, carriers, and Paragon leadership must be able to count on your availability for support, issue resolution, and scheduled meetings. Work performed primarily during evenings, nights, or weekends will not meet the needs of this engagement.

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

Employee benefits support and administration — approximately 80%

Employee advocacy and issue resolution

• Help employees navigate claims questions, coverage issues, ID cards, benefit transitions, and carrier resources.

• Investigate problems with carriers, administrators, and client contacts; track issues through resolution.

• Use plan documents and verified sources to explain benefits accurately and identify issues requiring escalation.

• Maintain clear records of questions, actions, outstanding items, and resolutions.

Eligibility, enrollment, and reconciliation

• Support new hires, qualifying life events, terminations, and recurring eligibility updates.

• 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.

• Review benefits invoices, investigate discrepancies, and coordinate corrections.

• Maintain dependable recurring processes across multiple employer clients.

Employee communications and client support

• Prepare clear benefit summaries, FAQs, employee communications, and open-enrollment materials.

• Verify plan details, contributions, dates, and links against approved sources.

• Support virtual employee education and benefits Q&A sessions.

• Participate in client meetings, document action items, and complete follow-up.

AI, employee engagement, and service improvement — approximately 20%

Use technology to help employees understand their benefit options, discover available programs, and take useful next steps throughout the year.

• Use approved AI tools to develop clear, engaging benefits communications from verified plan and carrier information.

• Create educational campaigns, presentations, FAQs, reminders, and digital resources that increase awareness of coverage options and available support.

• Help maintain benefits websites and resource pages that make accurate answers easier to find.

• Review recurring employee questions and available engagement information to identify communication gaps.

• Develop reusable templates and simple automations that improve service consistency.

• Validate AI-generated content against approved sources and protect confidential information.

You should be able to describe something you personally created or improved: the problem, audience, tools, your contribution, and how you checked its accuracy and usefulness.

What you bring

• At least five years of directly relevant employee-benefits experience, including hands-on administration and employee support. Experience within HR, a brokerage, consulting firm, or outsourced benefits team is welcome.

• Working knowledge of employer-sponsored medical, dental, vision, life, and disability benefits.

• Experience resolving issues with carriers and benefits vendors.

• Strong Excel skills, including lookups, filtering, file comparisons, duplicate identification, and reconciliation.

• Experience working with HRIS, payroll, or benefits administration systems.

• Practical use of AI or digital tools in professional work, including reviewing and validating output.

• Clear writing, patient communication, sound judgment, and consistent follow-through.

• The ability to manage recurring responsibilities and deadlines across multiple clients.

Experience with Dayforce, Paylocity, Rippling, Employee Navigator, Ease, BenefitSolver, or comparable platforms is helpful.

What success looks like

Employees receive clear answers and dependable follow-up. Enrollment records and benefits materials are accurate. Employees better understand their options and how to use available programs. Open items move toward resolution, and clients can count on your availability during the agreed schedule.

How to apply

Please submit your résumé and brief responses addressing:

1. A benefits issue you personally investigated and resolved.

2. An example of comparing enrollment, eligibility, or billing files and correcting discrepancies.

3. An AI or digital resource you created to improve employee education, benefits awareness, engagement, or service.

4. Your current city, state, and time zone, plus the recurring daytime days and hours you can commit to.

5. Confirmation that you seek a 25–35-hour contract engagement with Paragon as your primary professional engagement, without competing or conflicting commitments.

If available, include a relevant work sample using synthetic data or information you are authorized to share. Exclude confidential client, employee, and member information.