Benefits Manager

Benefits Manager toLead Self-Funded & Wellness Strategy – Help Build a Healthier Workplace

On-site at least 3 days a week at one of the following locations:

Des Plaines, IL (Chicago area) | Addison, TX (Dallas area) | Brookhaven, GA (North Atlanta area)

Full-Time | Exempt

Compensation: $120K–$140K + Bonus

Confidential Search – Posted by a trusted HR Executive Search Partner

About the Opportunity

A national professional services and real estate company, backed by a leading investment group, is seeking ahands-on, strategic Benefits Manager to lead and elevate its self-funded benefits and wellness strategy.

You will be responsible forowning and modernizing employee health benefits, wellness programs, compliance governance, and vendor partnerships across a workforce of 1,200+ employees.

This is a highly visible role: you will interact regularly with top executives and must be able to communicate with polish, clarity, and confidence at every level of the organization — building trust up, across, and down the leadership chain.

This role is perfect for a trueplayer-coach — someone who can seamlessly shift between strategic leadership and daily operational execution.

Why This Role Matters

This is more than a benefits administration role — it's astrategic leadership opportunity .

The company is evolving rapidly and needs a benefits leader who can:

• Drive smarter outcomes inhealth and wellbeing programs .

• Redesign thewellness strategy for 2025 and beyond.

• Ensure compliance strength forself-funded plans .

• Build a better benefits experience that supports employee retention, satisfaction, andorganizational health .

If you want to make avisible impact — this is your opportunity to shine.

What You’ll Own & Lead

Strategic Benefits Management

• Modernize and manageself-funded medical plans , 401(k) offerings, life, disability, and ancillary benefits.

• Proactively manage broker and vendor relationships —own the strategy , don't outsource it.

• Benchmark against industry trends to keep offerings competitive and sustainable.

Wellbeing Program Redesign & Execution

• Launch adata-driven wellness strategy that goes beyond flu shots — focusing on mental health, chronic disease prevention, nutrition, and holistic wellbeing.

• Tie wellness initiatives to measurable outcomes,employee engagement, and healthcare cost management.

Compliance & Governance Leadership

• Own end-to-end compliance processes for HIPAA, ACA, ERISA, ADA, FMLA, and 5500s.

• Manage nondiscrimination testing, audit preparation, and claims reporting for self-funded health plans.

Benefits Communication & Employee Education

• Build communication campaigns thattranslate complex benefits into clear, engaging education .

• Create a better onboarding and total compensation education experience for employees.

Leadership & Culture Building

• Supervise aBenefits & Leave Specialist, serving as amentor and escalation point.

• Act as a trusted partner to Total Rewards and HR Leadership in shaping the future of the employee experience.

Data-Driven Decision Making

• Leverage Workday (or similar HRIS), Excel, and vendor reporting to monitor plan performance and trends.

• Use insights to proactively recommend plan design improvements and engagement initiatives.

What Will Make You Successful

Hands-on experience with self-funded benefit plans (not just fully insured).

Strategic mindset and tactical follow-through — comfortable executing and leading.

Experience designing wellness programs tied to measurable outcomes.

Confident, polished communication skills — able to engage with employees and executives alike.

Collaborative but proactive leadership style — able to work independently when needed.

Strong knowledge of benefits compliance and U.S. regulations.

Analytical acumen to track trends, optimize plans, and drive smart decisions.

Requirements

• 5+ years of progressive experience in benefits leadership roles.

• Hands-on management ofself-funded health plans required.

• Bachelor’s degree required;CEBS or similar certification preferred .

• Experience supervising benefits specialists or HR team members.

• Strong knowledge of compliance requirements (HIPAA, ACA, ERISA, ADA).

• Comfort with HRIS platforms likeWorkday and proficiency with Excel.

Why Join This Company?

• Backed by a large leading investment group.

• High-growth environment with a focus on strategic HR leadership.

• Dynamic, collaborative, fast-paced workplace culture.

• Opportunity toown and elevate the entire benefits and well-being function.

• Make a visible, lasting impact on the organization's future.

This is a confidential search managed by Crucial Hire.