Overview of 66degrees 66degrees is an end-to-end AI transformation partner that guides enterprises from complex business challenges to clear, quantifiable outcomes. Our company is the culmination of several successful firms, each a leader in its own right in cloud, artificial intelligence, and data. This convergence of talent and expertise is how we help businesses reach their own "inflection point," where chaotic data becomes a strategic asset, complexity becomes clarity, and AI becomes an engine for growth. Our ultimate vision is to be the catalyst for a future where every business operates as an intelligent enterprise, with autonomous systems unlocking human potential. At 66degrees, we believe in thriving through challenges and winning together. These values not only guide us in achieving our goals as a company but also for our people. We are dedicated to creating a significant impact for our employees by fostering a culture that sparks innovation and supports professional and personal growth along the way. Overview of 66degrees 66degrees is an end-to-end AI transformation partner that guides enterprises from complex business challenges to clear, quantifiable outcomes. Our company is the culmination of several successful firms, each a leader in its own right in cloud, artificial intelligence, and data. This convergence of talent and expertise is how we help businesses reach their own "inflection point," where chaotic data becomes a strategic asset, complexity becomes clarity, and AI becomes an engine for growth. Our ultimate vision is to be the catalyst for a future where every business operates as an intelligent enterprise, with autonomous systems unlocking human potential. At 66degrees, we believe in thriving through challenges and winning together. These values not only guide us in achieving our goals as a company but also for our people. We are dedicated to creating a significant impact for our employees by fostering a culture that sparks innovation and supports professional and personal growth along the way. Overview of Role As a Benefits Specialist, you will serve as the cornerstone of our Total Rewards and People Operations team, ensuring our employees understand, value, and seamlessly access their health, wellness, and financial benefits. In this role, you will manage end-to-end daily benefits administration, lead employee inquiries with empathy and precision, and partner closely with HR, Payroll, and external carriers. You will combine hands-on operational excellence with regulatory compliance (ERISA, ACA, FMLA, COBRA), driving a frictionless benefits experience from onboarding through annual open enrollment. If you are a detail-oriented, service-driven HR professional who thrives in balancing analytical tasks with meaningful employee advocacy, this role offers an exciting opportunity to shape and elevate our employee wellbeing strategy. Employment Type - Contract for 6 months, ideally looking for immediate joiners. Responsibilities • Benefits Administration & Enrollment: Manage daily operations of group benefit programs (health, dental, vision, life, disability, and wellness plans). Process new hire enrollments, life event changes, and COBRA notifications. • Employee Support & Inquiry Resolution: Act as the primary point of contact for employees regarding benefits inquiries, claims escalation, coverage options, and policy interpretations. • Invoice & Billing Reconciliation: Reconcile monthly carrier invoices against payroll deductions and enrollment records, resolving discrepancies with providers and finance. • Leave of Absence (LOA) Management: Administer FMLA, STD/LTD, parental leave, and state-specific paid family leave programs in compliance with federal, state, and local laws.Open Enrollment Execution: Assist in planning, communications, platform testing, and execution of annual open enrollment periods and benefits wellness fairs. • Compliance & Reporting: Support compliance reporting and audits, including Form 5500 filings, ACA 1095-C tracking/reporting, non-discrimination testing, and maintaining Summary Plan Descriptions (SPDs). Qualifications • 2–4 years of direct experience in benefits administration, HR operations, or total rewards. • Hands-on experience with HRIS/benefits platforms (Rippling preferred) and advanced proficiency in Google Sheets • Experience transitioning a company from fully insured to self-funded. • Regulatory Knowledge: Solid understanding of federal and state regulations governing employee benefits (ERISA, ACA, COBRA, HIPAA, FMLA, Section 125). • Carrier & Vendor Management: Experience managing relationships and service-level agreements with insurance brokers, third-party administrators (TPAs), and carriers. • Communication & Discretion: Exceptional interpersonal and communication skills with a proven track record of handling sensitive and confidential employee data. • Superior time-management skills and the ability to juggle multiple operational tasks without letting details slip through the cracks. • Bachelor’s degree in Human Resources, Business Administration, or a related field, or equivalent practical experience. 66degrees is an Equal Opportunity employer. All qualified applicants will receive consideration for employment without regard to actual or perceived race, color, religion, sex, gender, gender identity, national origin, age, weight, height, marital status, sexual orientation, veteran status, disability status or other legally protected class. Please note, we cannot sponsor or transfer any visas, of any kind, at this time. 66degrees is an Equal Opportunity employer. All qualified applicants will receive consideration for employment without regard to actual or perceived race, color, religion, sex, gender, gender identity, national origin, age, weight, height, marital status, sexual orientation, veteran status, disability status or other legally protected class. AI Transparency & Disclosure As an AI transformation partner, 66degrees leverages intelligent solutions to enhance our recruitment experience. We utilize AI tools—including LinkedIn Recruiter’s Hiring Assistant and interview transcription technologies—to assist with sourcing, role analysis, and capturing interview highlights. These tools augment our process, but we "Commit to Our Craft" by ensuring all final hiring decisions are made by our human Talent Team. By applying, you acknowledge the use of these technologies to help us "Win Together" in finding the best fit for our team.