Benefits Specialist

The role

The Benefits Specialist manages daily operations of group benefit programs and employee inquiries. This role partners with HR, Payroll, and external carriers to ensure regulatory compliance and seamless benefits access.

What you will do

• Manage daily operations of group benefit programs including health, dental, vision, life, disability, and wellness plans.
• Process new hire enrollments, life event changes, and COBRA notifications.
• Act as the primary point of contact for employee benefits inquiries, claims escalation, and coverage options.
• Reconcile monthly carrier invoices against payroll deductions and enrollment records.
• Administer FMLA, STD/LTD, parental leave, and state-specific paid family leave programs.
• Assist in planning, communications, platform testing, and execution of annual open enrollment and wellness fairs.
• Support compliance reporting and audits including Form 5500 filings and ACA 1095-C tracking.
• Maintain Summary Plan Descriptions (SPDs).

Required qualifications

• 2–4 years of direct experience in benefits administration, HR operations, or total rewards.
• Hands-on experience with HRIS/benefits platforms.
• Advanced proficiency in Google Sheets.
• Experience transitioning a company from fully insured to self-funded.
• Solid understanding of federal and state regulations governing employee benefits (ERISA, ACA, COBRA, HIPAA, FMLA, Section 125).
• Experience managing relationships and service-level agreements with insurance brokers, third-party administrators (TPAs), and carriers.
• Exceptional interpersonal and communication skills.
• Proven track record of handling sensitive and confidential employee data.
• Superior time-management skills.
• Bachelor’s degree in Human Resources, Business Administration, or a related field, or equivalent practical experience.

Nice to have

• Rippling preferred

Before you apply

• We cannot sponsor or transfer any visas, of any kind, at this time.

About the company

66degrees is an end-to-end AI transformation partner that guides enterprises from complex business challenges to clear, quantifiable outcomes. The company is the culmination of several successful firms in cloud, artificial intelligence, and data.