Benefits Sales Executive Jobs in Chicago, IL

Senior Benefits & Compliance Specialist

Our Mission

NewRocket, a global, full-service Anthropic and Elite ServiceNow partner, helps top enterprise leaders solve their toughest business problems and navigate change with confidence. Our mission is to go beyond—creating meaningful experiences for our employees and customers. Our vision is to be the go-to ServiceNow Guide, creating extraordinary results with ServiceNow.

We've been recognized with multiple awards, including the 2024 BEST Award, 2024 ServiceNow Customer & Industry Workflows Delivery Success Partner, and 2023 ServiceNow Worldwide Customer Workflow Partner of the Year. We are #GoingBeyond.

Our Approach to Work

At NewRocket, people aren't just the backbone—they're the heartbeat of everything we do. We celebrate individuality, embrace diversity, and know innovation is born when unique perspectives collide. Work here is more than a job, it's a journey where:

• Balance matters – Success should never come at the expense of life outside work.

• Collaboration fuels us – Big ideas happen when teams move together.

• Growth is personal – Every voice counts, every contribution matters.

Bring your authentic self. Bring your curiosity. Bring your ambition. Together, we'll go beyond.

Overall Job Summary

The Senior Benefits & Compliance Specialist leads the administration, compliance, and continuous improvement of employee benefits programs across the U.S. and Canada. This role serves as a subject matter expert in benefits operations, regulatory compliance, and employee support, ensuring programs are competitive, compliant, and efficiently managed. The position partners closely with HR, Finance, vendors, and leadership to deliver a high-quality employee experience and support business objectives.

Key Job Responsibilities and Accountabilities

• Lead end-to-end administration of health, welfare, and retirement programs, including plan management, renewals, and ongoing operations.
• Manage and execute the annual Open Enrollment process, including system setup, employee communications, education, and reconciliation.
• Administer 401(k) and retirement programs, including enrollments, contributions, vendor coordination, and audit support.
• Partner with brokers and vendors to evaluate plan performance, resolve escalations, and recommend enhancements to offerings.
• Ensure compliance with federal, state, and company requirements related to benefits, leave, and employee records (e.g., ERISA, ACA, HIPAA, ADA, FMLA, COBRA).
• Conduct and support compliance audits, including I-9 audits, employee file reviews, and benefits-related reporting requirements.
• Manage required regulatory filings, notices, and documentation associated with employee benefits programs.
• Oversee administration of leave programs, including FMLA, state leaves, and company policies, ensuring compliance and a positive employee experience.
• Serve as the primary point of contact for employee benefits inquiries, providing guidance on plan options, eligibility, and issue resolution.
• Support onboarding and offboarding processes with a focus on benefits enrollment, transitions, and eligibility.
• Drive continuous improvement of benefits processes, documentation, and workflows to increase efficiency and scalability.
• Support HRIS-related initiatives and system integrations (e.g., ADP), ensuring accuracy and process consistency.
• Manage employment verifications and maintain strict confidentiality of sensitive employee data.
• Collaborate with HR, Finance, Legal, and external vendors to support benefits strategy and compliance initiatives.
• Provide insights and reporting to leadership on benefits trends, utilization, and compliance risks.

Skills, Knowledge, and Abilities

• Minimum of 5 years of progressively responsible experience in benefits administration, HR operations, leave administration, or compliance
• Experience administering benefits programs in the U.S. and Canada, ideally within a multi-national organization
• Strong knowledge of U.S. and Canadian benefits practices and applicable employment regulations, including health, welfare, and retirement programs
• Experience managing annual Open Enrollment processes, retirement plans, and HRIS platforms such as ADP
• Ability to work effectively in fast-changing environments with strong decision-making, influencing, analytical, and organizational skills
• Ability to handle sensitive and confidential information with discretion

We Take Care of Our People

NewRocket is committed to a diverse and inclusive workplace. We value and celebrate diversity, believing that every employee matters and should be respected and heard. We are proud to be an equal opportunity workplace and affirmative action employer, committed to providing employment opportunity regardless of sex, race, creed, color, gender, religion, marital status, domestic partner status, age, national origin, or ancestry, physical or mental disability, medical condition, sexual orientation, pregnancy, citizenship, military, or Veteran status. For individuals with disabilities who would like to request an accommodation, please contact hr.us@newrocket.com