Senior Human Resources Generalist

Addison Group; Chicago (IL); On-site; USD 75,000 - 85,000; Full time

Benefits offered by this job

Medical benefits

Dental benefits

Vision benefits

401(k)

Job summary

Addison Group seeks a Senior People & Culture Generalist with a strong benefits administration focus to join our Chicago-based HR team. You will oversee benefits across multiple affiliated organizations, support leave administration, employee relations, compliance, and HR operations, and mentor junior staff.

The role requires hands-on benefits expertise, knowledge of employment regulations, and excellent communication to guide employees and managers through programs and policies in a fast-paced,

Qualifications

• 5+ years of HR or People & Culture experience preferred.
• Minimum of 2 years of hands-on employee benefits administration experience.
• Bilingual fluency in English and Spanish required.
• Experience with HRIS platforms and benefits programs.

Responsibilities

• Manage day-to-day administration of employee benefit programs across multiple organizations.
• Oversee benefits activities for affiliated organizations with varying plan structures.
• Lead benefits education for new hires and provide ongoing guidance to employees.
• Coordinate annual open enrollment processes and related communications.
• Process benefit elections and changes due to qualifying life events.
• Review carrier invoices and ensure accurate payroll deductions.

Skills

Bilingual English/Spanish

Benefits administration

HR experience

Tools

Paylocity

Job description

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).

About The Company:

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.

Job Description:

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.

Key Responsibilities:

• 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.

Qualifications:

• 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 required; Paylocity experience is preferred but not required.
• Employee relations and workplace investigation experience is a plus.
• Previous nonprofit, healthcare, or human services experience is preferred.
• Strong interpersonal and conflict‑resolution skills with the ability to work effectively with employees at all levels.
• Excellent attention to detail, organization, and time management skills.
• Ability to prioritize multiple responsibilities in a fast‑paced HR environment.
• Strong written and verbal communication skills.
• Proficiency with Microsoft Office Suite.
• Ability to handle sensitive employee information with discretion and confidentiality.
• SHRM‑CP, SHRM‑SCP, PHR, or SPHR certification is a plus.
• The role will oversee benefits administration across multiple affiliated organizations, including employee populations with different benefit structures.
• The organization is working toward greater consistency across its benefit programs.
• Occasional travel to additional local sites may be required.
• This position will play an important role in strengthening the team's overall benefits knowledge and processes.
• Permanent opportunity with an established nonprofit organization.
• High‑visibility role with ownership of benefits administration.
• Opportunity to mentor and develop other HR team members.
• Broad exposure across benefits, employee relations, compliance, leave administration, and HR operations.
• Mission‑driven organization focused on serving the local community.

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non‑discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request.