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Sr. Benefits Specialist

Alera Group

Chicago, Illinois

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JOB DETAILS
SKILLS
Administrative Skills, Americans with Disabilities Act (ADA), Auditing, Brokerage, COBRA (Consolidated Omnibus Budget Reconciliation Act of 1985), Compensation and Benefits, Documentation, Documentation Standards, Employee Benefits, Funding, HRIS/HRMS, Healthcare Administration, Maintain Compliance, Process Improvement, Retirement Plan, Retirement and Pension Management, Risk, Team Player, Time Management, Web Site Monitoring, Worker's Compensation
LOCATION
Chicago, Illinois
POSTED
30+ days ago
OVERVIEW

Benefits Specialist - Employee Benefits
Remote |

At Alera Group, we help businesses navigate risk with confidence. Our Employee Benefits teams deliver thoughtful, people-centered solutions that support organizations and the employees they serve. We're hiring a Benefits Specialist who will play a key role in administering leave and benefits programs while ensuring compliance, accuracy, and a strong employee experience.

This role serves as a subject-matter expert in leave of absence programs and partners closely with HR, Payroll, vendors, and employees to ensure seamless, compliant operations across multiple jurisdictions.

About the Role
The Benefits Specialist is responsible for overseeing leave of absence programs while supporting core benefits administration. This role partners closely with internal teams and external vendors to ensure accurate, timely, and compliant execution of leave and benefits processes.

Success in this role looks like delivering a seamless employee experience, maintaining strong compliance across evolving regulations, and ensuring operational accuracy across leave and benefits programs.

About Alera Group
Founded in 2017, Alera Group has grown to become the 14th largest broker of U.S. business. We are passionate about our clients' success in Employee Benefits, Property & Casualty Insurance, and Financial Services. With offices nationwide, our collaborative approach allows us to deliver national strength with local service.

If you're someone who enjoys navigating complexity, ensuring compliance, and supporting employees through important life events, this is an opportunity to make a meaningful impact while growing your expertise in benefits and leave administration.

Why Join Alera Group
  • Make an impact across the organization - Support colleagues and leaders who serve clients nationwide.
  • Be part of a collaborative culture - Work with talented professionals across regions and business lines.
  • Grow your career - Access development opportunities and resources that support long-term career growth.

RESPONSIBILITIES

What You'll DoLeave Administration & Compliance
  • Oversee and coordinate all leave of absence programs, including FMLA, ADA, disability, workers' compensation, and state/local statutory leaves
  • Serve as the primary liaison with leave, disability, and workers' compensation vendors
  • Interpret and apply federal, state, and local leave laws to ensure compliance across multiple jurisdictions
  • Guide employees, managers, and HR partners on leave policies, processes, and responsibilities
  • Coordinate return-to-work processes and ADA accommodations in partnership with HR and vendors
  • Partner with Payroll to ensure accurate pay impacts, benefit continuation, and leave status tracking
  • Monitor state leave portals and ensure compliance with required deadlines
  • Audit leave data and documentation to ensure accuracy and consistency
Benefits Administration
  • Support administration of health, welfare, and retirement programs, including COBRA compliance
  • Manage eligibility, enrollments, and terminations with a high degree of accuracy
  • Respond to employee inquiries regarding medical, dental, vision, retirement, and leave-related benefits
  • Assist with retirement plan administration, including funding, audits, and reporting
  • Support 401(k) inquiries including contributions and enrollment changes
  • Perform audits and quality checks within HRIS and vendor systems
  • Support open enrollment planning, testing, and execution
Program Support & Collaboration
  • Partner with vendors, consultants, Payroll, and HR teams on data, eligibility, and compliance interpretation
  • Participate in compliance and technical discussions related to leave and benefits programs
  • Support new hire orientation by explaining benefits and leave offerings
  • Maintain documentation standards to ensure accurate and consistent records
  • Contribute to process improvements that enhance efficiency and employee experience
QUALIFICATIONS

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About the Company

A

Alera Group

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