Benefits Specialist Contractor
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-10-04
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HR/Recruitment
Regulatory Compliance Specialist, HR Generalist / Talent Management
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Benefits Specialist Contractor based in United States.
This role is responsible for managing leave of absence and workplace accommodation programs across U.S. and international locations.
You will serve as a trusted point of contact for employees and managers, guiding them through eligibility, documentation, timelines, and return-to-work processes.
The position combines benefits administration, compliance, case management, and employee support in a highly collaborative environment.
You will work closely with HR, Legal, Payroll, Benefits, insurance carriers, third-party administrators, and international HR partners.
The role also involves leading ADA accommodation processes and ensuring sensitive employee information is handled appropriately.
You will contribute to policy development, program reporting, training, and continuous process improvement.
This is a full-time remote contractor opportunity requiring strong judgment, organization, empathy, and knowledge of leave and accommodation regulations.
AccountabilitiesAdminister and communicate leave programs across U.S. and international locations, including FMLA, state and local leave, paid and unpaid leave, short- and long-term disability, parental leave, USERRA, and applicable statutory programs.
Serve as the primary contact for employees and managers, providing clear and empathetic guidance regarding eligibility, documentation, timelines, job protections, and required procedures.
Manage leave intake, case tracking, documentation, recordkeeping, and resolution while coordinating with third-party administrators, insurance carriers, and international HR partners.
Own leave cases from initial intake through return-to-work, escalating jurisdiction-specific legal questions to appropriate HR and Legal partners.
Partner with Payroll and Benefits to ensure appropriate pay treatment, benefits continuation, and return-to-work processing.
Monitor federal, state, and international leave requirements and support updates to policies, procedures, communications, and processes.
Maintain confidentiality of employee medical and leave information and support internal or external audits through accurate documentation and compliance controls.
Lead the interactive process for ADA accommodation requests, partnering with employees, managers, HR business partners, and Legal to evaluate requests, identify accommodations, and document outcomes.
Track accommodation requests and resolutions to promote timely case management and consistent application of policies.
Develop and maintain leave policies, employee communications, FAQs, manager guidance, and related documentation.
Monitor leave and accommodation metrics, identify trends, and recommend improvements to processes, technology, and workflows.
Provide training and guidance to HR business partners and people leaders on leave, accommodation policies, procedures, and management responsibilities.
Perform additional benefits, leave, accommodation, or program-management duties as required.
Bachelor's degree in Human Resources, a related field, or equivalent practical experience.
At least 2 years of experience administering leave of absence programs, including FMLA, ADA, and state or local leave requirements.
Experience administering or coordinating leave and accommodation programs across multiple countries is required.
In-depth working knowledge of U.S. federal and state leave and accommodation regulations, along with applicable international requirements.
Demonstrated experience managing ADA interactive processes and accommodation cases from intake through resolution.
Experience working with third-party leave or disability administrators, insurance carriers, and HR or Legal partners.
Ability to collaborate with in-country HR and Legal teams to apply local employment requirements in a multinational environment.
Strong organizational skills and attention to detail, with the ability to manage a high volume of concurrent and sensitive cases.
Excellent written and verbal communication skills, with the ability to explain complex policies clearly and empathetically to employees and managers.
Strong discretion, sound judgment, and commitment to confidentiality when handling sensitive employee and medical information.
Proficiency with HRIS and leave-management platforms such as Workday, ADP, Service Now, or comparable systems.
Proficiency with…
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