--- title: 'Benefits Specialist at 66degrees' canonical: 'https://feeny.ai/job/benefits-specialist-66degrees-chicago-gdh7tdcqzsj3' type: 'job' last_seen: '2026-11-07' --- # Benefits Specialist at 66degrees - **Company:** 66degrees - **Location:** Chicago, IL - **Posted:** 2026-09-29 - **Last confirmed live:** 2026-11-07 - **Apply:** https://job-boards.greenhouse.io/66degrees/jobs/6210727004 ## Job description ## 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. ## About 66degrees ## Company Overview - **One-liner**: 66degrees is an enterprise AI transformation and Google Cloud partner that helps organizations build intelligent, agentic systems by modernizing data, applications, and infrastructure. - **Entity Type**: Private (acquired by The Marketing Junction in February 2026) - **Headquarters**: Chicago, Illinois, United States - **Founded**: 2009 - **Founders**: Not publicly available (the company was formed through the merger of Cloudbakers and Qwinix) ## Core Business - **Primary industries**: Enterprise AI/ML services, Google Cloud consulting and implementation, data analytics, application modernization - **Target customers**: Large enterprises across retail, healthcare & life sciences, financial services, travel & hospitality, supply chain, manufacturing, and energy/utilities (B2B, Enterprise) - **Mission or purpose statement**: “To guide enterprises through the age of AI and shape the future of work” – helping clients turn complexity into clarity by building the Agentic Enterprise. ## Products & Services - **Agentic AI**: Design and deploy custom AI agents that orchestrate complex business workflows, automate customer touchpoints, and improve employee productivity. - **Data & Analytics**: Data strategy, governance, predictive analytics, and AI-ready platform modernization (leveraging BigQuery, Vertex AI, etc.). - **Application Modernization**: Develop cloud-native apps on Google Cloud integrated with AI/ML services for agility and scalability. - **Customer Engagement Suite**: AI-driven customer experiences using Google Cloud’s contact center tools (e.g., Gemini) to enhance satisfaction and reduce costs. - **Gemini Enterprise**: Enterprise adoption of Google’s Gemini models for productivity and innovation. - **Infrastructure**: Migration and modernization of legacy infrastructure to a unified, AI-ready cloud platform. - **Managed Services & MLOps/LLMOps**: Ongoing performance monitoring, cost management, and governance for AI models in production. ## Market Standing - **Valuation/Market Cap**: Not disclosed - **Key Metric**: Total Funding – Not publicly available (no public funding rounds; growth has been organic and through acquisitions) - **Notable Investors/Partners**: - **Google Cloud** – Diamond Partner, multi-year Partner of the Year for AI and North American expansion - **The Marketing Junction** – acquirer (February 2026) - **Growth Signals**: - Opened a Chicago Global Headquarters and Client Innovation Center in 2025 - Added offices in Pune, India (3rd global office) and expanded Bengaluru Indian HQ - 2025 Google Cloud Partner of the Year for Artificial Intelligence - Claims 90% automation of customer touchpoints for a travel & hospitality leader and $10M annual savings for a Fortune 250 client - Grew AI/ML practice significantly year-over-year in 2024 ## Competitive Advantages - **Deep Google Cloud Specialization**: Only a handful of firms hold Diamond Partner status across AI, Data & Analytics, and Infrastructure competencies. - **Proven Client ROI**: Demonstrates quantifiable results (e.g., $10M savings, 70% automation, 4x improvements in call center quality). - **Agentic AI Lifecycle Management**: End-to-end capabilities from strategy to deployment to ongoing governance (MLOps/LLMOps). - **Combined Expertise**: Convergence of top-tier firms (Cloudbakers, Qwinix, Pandera Systems) creating a dedicated, cohesive practice focused solely on Google Cloud and AI. ## Strategic Focus - **Agentic Enterprise**: Helping clients move beyond AI pilots to production-ready agentic systems that transform business workflows. - **Data Modernization**: Building unified, AI-ready data platforms from fragmented legacy systems. - **Global Scale**: Expanding delivery footprint across North America, India, and Europe to serve enterprise clients. - **Continuous AI Governance**: Ensuring AI investments are predictable, secure, and cost-efficient through managed services. ## Why Work Here - **Cutting-Edge Technology**: Work with Google Cloud’s latest AI/ML tools (Vertex AI, Gemini, BigQuery) before they become mainstream. - **Impact at Scale**: Deliver measurable outcomes for global brands – e.g., saving millions in costs or automating majority of customer interactions. - **Growth and Learning**: Multi-year Partner of the Year recognition indicates strong career development opportunities and access to elite training. - **Culture**: Described as a “convergence of world-class engineers, architects, and strategists” with shared purpose and passion. - **Work Model**: Offices in Chicago (HQ), Bengaluru, and Pune; remote/hybrid policy not explicitly stated – likely flexible given global team structure. - **Benefits**: Focus on driving quantifiable impact, innovation, and working on “the most ambitious and complex challenges.” ## Sources 1. [66degrees.com](https://www.66degrees.com/) 2. [About Us – 66degrees](https://www.66degrees.com/about-us) 3. [Careers – 66degrees](https://www.66degrees.com/careers) 4. [CBInsights – 66degrees](https://www.cbinsights.com/company/66degrees) 5. [LinkedIn – 66degrees](https://www.linkedin.com/company/66degrees) ## Other roles at 66degrees - [Vice President of Sales, West](https://feeny.ai/job/vice-president-of-sales-west-66degrees-western-region-rcxjr2nyaynj) — Western Region, United States - [AI/ML Architect](https://feeny.ai/job/ai-ml-architect-66degrees-india-84yk572wzk3f) — India - [Security PAM Engineer](https://feeny.ai/job/security-pam-engineer-66degrees-united-states-2s4pj9zhhenk) — United States - [Associate Delivery Consultant, Gradient Specialist](https://feeny.ai/job/associate-delivery-consultant-gradient-specialist-66degrees-chicago-j3z2jyn9w993) — Chicago, IL - [Senior Manager - Sales](https://feeny.ai/job/senior-manager-sales-66degrees-bengaluru-anapsw8ad64j) — Bengaluru, India - [Technical Support Specialist (Jira)](https://feeny.ai/job/technical-support-specialist-jira-66degrees-bengaluru-qds625pxzrh8) — Bengaluru, India - [Security Operations AI Engineer, Contract](https://feeny.ai/job/security-operations-ai-engineer-contract-66degrees-united-states-qbzaa5ep1hhf) — United States - [Enterprise Account Executive, East](https://feeny.ai/job/enterprise-account-executive-east-66degrees-atlanta-66wqey3aeaav) — Atlanta, GA - [Site Reliability Engineer](https://feeny.ai/job/site-reliability-engineer-66degrees-bengaluru-49rtdxprpydn) — Bengaluru, India - [Enterprise Account Executive, West](https://feeny.ai/job/enterprise-account-executive-west-66degrees-san-francisco-hpj95mnrsh39) — San Francisco, CA