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Benefits Specialist

The Equus Group
Chicago, IL Full Time
POSTED ON 6/2/2026
AVAILABLE BEFORE 7/1/2026

Benefits Manager


About the role

A top-tier Chicago-based private equity firm is seeking a Benefits Manager to own and evolve its benefits program across a lean, high-performing workforce. You will serve as the subject matter expert on health, welfare, retirement, and executive compensation programs — managing vendor relationships, ensuring compliance, and delivering a best-in-class employee experience. This is a high-visibility role suited for someone who thrives in a fast-paced, analytically driven environment and can operate with a broad scope of responsibility across a multi-jurisdictional employee population.


Responsibilities

  • Own end-to-end administration of U.S. and international health, welfare, and retirement benefit plans, ensuring programs remain competitive, cost-effective, and compliant across jurisdictions
  • Manage the full suite of benefit programs including medical, dental, vision, life, disability, FSA/HRA/HSA, EAP, student debt, commuter, voluntary, and Workers' Compensation programs
  • Lead annual open enrollment end-to-end — including communications strategy, Workday system configuration, testing, auditing, and employee education sessions
  • Oversee 401(k) and deferred compensation plan administration in partnership with record-keepers and investment advisors; manage plan audits and resolve compliance issues as they arise
  • Ensure compliance with ERISA, ACA, HIPAA, COBRA, FMLA, ADA, Section 125, and applicable state and international regulations; manage Form 5500 filings, EEO-1 reports, 1095-C reporting, and required plan notices
  • Manage and regularly evaluate broker and vendor relationships; conduct periodic benchmarking and RFP processes to ensure program quality and cost competitiveness
  • Monitor workforce trends, regulatory changes, and market benchmarks; develop and present plan change recommendations to HR leadership
  • Develop and execute benefits communications across the employee lifecycle — new hire orientation, open enrollment, leave events, and retirement transitions
  • Partner with Payroll and Finance on benefits funding, billing reconciliation, and accurate payroll deductions
  • Support M&A due diligence and integration activities related to portfolio company benefits as needed
  • Serve as a responsive escalation point for employee benefits questions and complex claims issues


Qualifications

  • 6 years of benefits administration or management experience
  • Prior exposure to financial services, PE, or similarly complex professional services environments preferred
  • Strong working knowledge of ERISA, ACA, HIPAA, and COBRA compliance requirements
  • Experience managing broker relationships and conducting vendor RFPs
  • Proficiency with HRIS platforms (Workday, ADP, or equivalent)
  • High comfort with data — able to build and interpret benefits analytics independently
  • CBP, CEBS, or PHR designation a plus
  • Bachelor's degree required


Attributes they value

  • Operates with a high degree of autonomy and accountability
  • Clear, concise communicator — written and verbal
  • Comfortable working in a small team with a broad scope of responsibility
  • Detail-oriented with strong project management instincts
  • Handles confidential information with discretion and professionalism
  • Proactive — identifies gaps and acts on them before they become problems


The Equus Group is an Equal Opportunity Employer and takes pride in maintaining a diverse environment. We do not discriminate in recruitment, hiring, training, promotion, or any other employment practices for reasons of race, color, religion, gender, national origin, age, sexual orientation, marital or veteran status, disability, or any other legally protected status.

Salary.com Estimation for Benefits Specialist in Chicago, IL
$74,161 to $89,978
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