Senior People & Culture Generalist - Bilingual

Job Title: Senior People & Culture Generalist - Bilingual

Industry: Nonprofit

Location: Chicago, IL – Northwest Side

Assignment Type: Direct Hire

Pay: $75,000–$85,000 annually

Work Schedule: Monday–Friday, 8:00 AM–5:00 PM | 100% On-Site

Benefits: This position is eligible for medical, dental, vision, and 401(k).

A long-established nonprofit organization providing essential community and human services throughout the Chicago area. The organization offers a mission-driven environment with a collaborative People & Culture team and a strong focus on employee development, engagement, and long-term organizational growth.

We are seeking an experienced Senior People & Culture Generalist with a strong specialization in benefits administration to join a growing HR team. This position will oversee employee benefits across multiple affiliated organizations while also providing support in leave administration, employee relations, compliance, performance management, and broader HR operations.

The ideal candidate will bring hands-on benefits expertise, strong knowledge of employment regulations, and the confidence to serve as a go-to resource for employees and fellow HR team members. This individual will also help mentor and develop other team members by sharing benefits knowledge and establishing consistent processes.

• Manage day-to-day administration of employee benefit programs, including health, dental, vision, life, disability, retirement, and voluntary plans.
• Oversee benefits activities for multiple affiliated organizations with varying plan structures.
• Lead benefits education for new hires and provide ongoing guidance to employees regarding available programs.
• Coordinate the annual open enrollment process, including communications, employee education, and enrollment assistance.
• Process benefit elections and changes resulting from qualifying life events.
• Review monthly carrier invoices and confirm employee payroll deductions are accurate.
• Maintain relationships with insurance carriers, brokers, and other benefits partners.
• Act as a primary resource for employees with questions regarding benefits eligibility, coverage, and plan options.
• Administer employee leave programs, including FMLA, ADA accommodations, paid and personal leaves, military leave, and workers' compensation.
• Track leave documentation, balances, employee status, and return-to-work information while maintaining confidentiality.
• Provide guidance to managers and employees regarding workplace concerns and HR policies.
• Assist with employee relations matters, investigations, coaching conversations, corrective actions, and conflict resolution.
• Support compliance with federal, state, and local employment regulations and maintain audit-ready HR documentation.
• Coordinate onboarding, offboarding, employee status changes, and other employee lifecycle activities.
• Maintain accurate employee information within the HRIS and assist with HR reporting and data analysis.
• Partner with payroll to ensure benefit deductions, leave information, and employment changes are processed correctly.
• Support annual performance reviews, coaching initiatives, development plans, and performance improvement processes.
• Contribute to employee engagement, recognition, wellness, and workplace culture initiatives.
• Mentor and support other HR team members by sharing benefits expertise, processes, and best practices.
• Assist with special People & Culture initiatives and continuous improvement projects.

• Approximately 5+ years of HR or People & Culture experience preferred.
• Minimum of 2 years of hands‑on employee benefits administration experience required.
• Bilingual fluency in English and Spanish required.
• Strong knowledge of employee benefits with the ability to clearly explain plans and programs to employees.
• Experience administering FMLA, ADA accommodations, workers' compensation, and other employee leave programs.
• Working knowledge of COBRA, HIPAA, ACA, EEOC, wage and hour requirements, and related employment regulations.
• Previous experience mentoring, training, or providing guidance to other HR team members.
• Experience with HRIS platforms…