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The Benefits and Leave Specialist provides support for benefits administration and leave compliance, ensuring timely assistance and maintaining employee records while navigating complicated situations and regulations.
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As a Benefits Administration Specialist, you will work with payroll service bureaus or PEO in HRIS, Benefits, or Time modules using various systems.
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The Benefits Specialist administers employee benefit programs, serves as a contact for inquiries, manages enrollment processes, and ensures compliance with regulations.
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AHEAD builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation.
At AHEAD, we prioritize creating a culture of belonging, where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD.
We are an equal opportunity employer, and do not discriminate based on an individual's race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, marital status, or any other protected characteristic under applicable law, whether actual or perceived.
We embrace all candidates that will contribute to the diversification and enrichment of ideas and perspectives at AHEAD.
The Benefits Specialist is responsible for the day-to-day administration, auditing, and support of employee benefit programs. This role partners closely with Payroll, HR, and external vendors to ensure accurate enrollments, billing, compliance, and employee support across a large benefits population.
Roles & Responsibilities
- Administer employee benefit programs, including medical, dental, vision, FSA, retirement, and ancillary benefits.
- Manage new hire benefit enrollments and process qualifying life events (QLEs).
- Complete manual enrollments with carriers as needed.
- Maintain and update dependent, beneficiary, deduction, and benefit group records in the HRIS.
- Upload and administer mobile phone stipend deductions.
- Support open enrollment execution and employee communications.
- Review and reconcile monthly benefits billing for accuracy.
- Conduct regular audits of benefit deductions, enrollments, and payroll files.
- Support FSA payroll deductions and ongoing reconciliation.
- Provide initial, day-to-day employee support for basic benefits questions.
- Serve as a first point of contact for benefits inquiries, escalating complex issues when appropriate.
- Partner with internal stakeholders and vendors to resolve benefit-related issues efficiently.
- Ensure benefit administration aligns with applicable laws and regulations, including ACA, COBRA, FMLA, ADA, 401(k), OSHA, and other relevant requirements.
- Maintain accurate records within HRIS and benefits systems, with a strong emphasis on data integrity.
- Support benefits processes within UKG and related systems.
Qualifications
- Minimum of 3+ years of experience administering benefits for large benefit programs.
- Strong understanding of payroll deductions and benefit taxation.
- Hands-on experience with HRIS and benefits systems, preferably UKG.
- Working knowledge of benefit-related laws and regulations (ACA, COBRA, FMLA, ADA, 401(k), OSHA, etc.).
- Experience supporting or administering self-funded benefit plans.
- Advanced organizational skills with the ability to be thorough, efficient, and effective.
- Strong problem-solving skills, including knowing when to escalate issues.
- Ability to multitask and remain calm under pressure, especially during peak periods.
- Excellent verbal and written communication skills.
- Proficiency in Excel.
- Willingness and ability to learn new systems, processes, and regulations.
- Flexibility to work non-standard hours during busy seasons (e.g., open enrollment).
- Proactive mindset with the ability to bring forward process improvements and new ideas.
- Strong attention to detail with a service-oriented approach.
- Ability to collaborate effectively across HR, Payroll, Finance, and external vendors.
Why AHEAD:
Through our daily work and internal groups like Moving Women AHEAD and RISE AHEAD, we value and benefit from diversity of people, ideas, experience, and everything in between.
We fuel growth by stacking our office with top-notch technologies in a multi-million-dollar lab, by encouraging cross department training and development, sponsoring certifications and credentials for continued learning.
USA Employment Benefits include:
- Medical, Dental, and Vision Insurance
- 401(k)
- Paid company holidays
- Paid time off
- Paid parental and caregiver leave
- Plus more! See benefits https://www.aheadbenefits.com/ for additional details.
The compensation range indicated in this posting reflects the On-Target Earnings (“OTE”) for this role, which includes a base salary and any applicable target bonus amount. This OTE range may vary based on the candidate’s relevant experience, qualifications, and geographic location.
AHEAD Chicago, Illinois, USA Office
401 N Michigan Ave, Chicago, IL, United States, 60611
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
