Benefits Analyst (AI)

Location: Chicago, IL; US-based applicants must be authorized to work in the United States.

Salary: $64,600.00–$79,150.00 base salary per year; some roles may also be eligible for bonus and/or equity programs.

Company

hirify.global provides automotive marketplace, digital retail, trade and appraisal, wholesale auction, and media technology products.

What you will do

• Administer U.S. and Canadian medical, dental, vision, life, disability, FSA/HSA, commuter, COBRA, 401(k), and leave programs, including enrollments, eligibility, qualifying life events, and terminations.
• Configure and maintain benefits and absence programs in Workday, support HRIS releases and testing, and lead annual open enrollment.
• Process vendor billing, invoices, funding approvals, reconciliations, LOA commission calculations, and benefits data reporting.
• Administer FMLA, parental, caregiver, medical, military, and state paid leave programs in partnership with the leave vendor, HR Business Partners, Payroll, and Legal.
• Maintain benefits and leave intranet content, communications calendars, employee emails, FAQs, guides, and webinars.
• Use AI tools and emerging technologies to automate repetitive work and improve operational efficiency.

Requirements

• Bachelor’s degree in Human Resources, Business, or a related field, or equivalent experience.
• 3–6 years of experience administering employee benefits and/or leaves of absence.
• Working knowledge of FMLA, ACA, COBRA, ERISA basics, and state paid leave and paid sick requirements, including monitoring and interpreting changing federal, state, and local requirements.
• Hands-on HRIS experience; Workday benefits configuration experience is strongly preferred.
• Strong analytical skills and advanced Excel or Google Sheets skills, including lookups, pivots, and data reconciliation.
• Excellent attention to detail, ability to manage recurring payroll, invoice, and enrollment deadlines, and clear written and verbal communication.
• Ability to manage confidential medical and personal information with sound judgment.
• Ability to work with multiple vendors, Payroll, HR Business Partners, and Legal.
• Demonstrated curiosity and proficiency with AI tools such as Gemini, Claude, Copilot, or role-specific AI platforms, plus willingness to evaluate and adopt AI capabilities.
• Tools and systems include Workday Benefits and Absence, Google Workspace, and Microsoft Office.

Nice to have

• Experience with U.S. and Canadian benefits, including group health, RRSP, or Canadian leave requirements.
• Experience with leave vendor platforms and benefits consultants or brokers.
• Experience supporting open enrollment and employee communications.
• Professional certification such as PHR, SHRM-CP, CEBS, or CLMS.

Culture & Benefits

• Collaborative environment centered on openness, ownership, integrity, and constructive challenge.
• Medical, dental, and vision healthcare plans.
• New-hire stipend for home office setup.
• Generous PTO, paid holidays, floating holiday, volunteer day, and recharge day.
• Regular full-time employees are eligible for a comprehensive benefits package.