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, ID cards, 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.
• Maintain reliable recurring processes across multiple employer clients.

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 education and benefits Q&A sessions.
• Participate in client meetings, document action items, and complete follow-up.
• Coordinate with Paragon leadership on priorities, deadlines, and service needs.

AI, EMPLOYEE ENGAGEMENT, AND PROCESS 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 turn complex plan and carrier information into clear, engaging communications tailored to each client’s benefits.
• Develop educational campaigns, presentations, FAQs, reminders, and digital resources that build awareness of coverage options, preventive care, and available support programs.
• Help employees understand when and how to use their benefits through timely communications around enrollment, life events, and recurring benefits questions.
• Help maintain accessible benefits websites, resource pages, and guided information tools that make answers easier to find.
• Review recurring employee questions and available engagement data to identify information gaps and improve future communications.
• Build reusable templates, prompts, checklists, and simple automations that improve service consistency and reduce manual work.
• Validate AI-generated content against approved sources and protect confidential employee and client information.

You should be able to explain something you personally created or improved: the audience or problem, the tools you used, 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. Benefits 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, including eligibility, enrollment, and common service issues.
• Experience investigating and resolving issues with carriers and benefits vendors.
• Strong Excel skills, including lookups, filtering, comparing files, identifying duplicates, and reconciling discrepancies.
• Experience extracting or managing information in HRIS, payroll, or benefits administration systems.
• Practical experience using generative AI in professional work, with the ability to demonstrate how you review and validate its output.
• The ability to translate technical benefits information into communications employees can understand and act on.
• Clear writing, patient communication, sound judgment, and consistent follow-through.
• The ability to manage recurring responsibilities and deadlines across multiple clients independently.
• Availability for a consistent, agreed daytime schedule of 25–35 hours per week.

Experience with Dayforce, Paylocity, Rippling, Employee Navigator, Ease, BenefitSolver, or comparable platforms is helpful. Experience creating employee education campaigns, digital benefits resources, or workflow automations is also valuable.

WHAT SUCCESS LOOKS LIKE

Employees receive clear answers and dependable follow-up. Enrollment records and benefits materials are accurate. Employees become more aware of their options and better understand how to use available benefits and programs. Open items move toward resolution without repeated reminders, and clients can count on your availability during the agreed schedule.

The scope centers on benefits service and operations; sales, carrier marketing, underwriting, and primary financial reporting are outside the engagement.

HOW TO APPLY

Please submit your résumé and brief responses to the following:

1. Describe a benefits issue you personally investigated and resolved. What did you do, and what was the outcome?
2. Describe how you have compared enrollment, eligibility, or billing files to identify and correct discrepancies.
3. Give one specific example of using AI or digital tools to improve employee education, benefits awareness, engagement, or a related service process. Explain your contribution and how you verified the result.
4. Confirm that you are seeking a contract engagement of 25–35 hours per week and can make Paragon your primary professional engagement without competing or conflicting commitments.
5. Specify the recurring days and daytime hours you can commit to, including your time zone. Confirm that you are located in the Eastern or Central Time Zone and can support employees, clients, and carriers during the agreed Eastern Time business-day schedule.

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