Benefits Manager

Crucial Hire; Des Plaines (IL); On-site; USD 120,000 - 140,000; Full time

Benefits offered by this job

High-growth environment

Dynamic, collaborative workplace culture

Opportunity to own benefits function

Job summary

A national professional services and real estate company is seeking a strategic Benefits Manager to lead its self-funded benefits and wellness strategy. This role involves modernizing employee health benefits, ensuring compliance, and enhancing the overall benefits experience for over 1,200 employees. The ideal candidate will have a strong background in benefits leadership and a collaborative leadership style.

Qualifications

• 5+ years of progressive experience in benefits leadership roles.
• Hands-on management of self-funded health plans required.
• Experience supervising benefits specialists or HR team members.

Responsibilities

• Lead and elevate self-funded benefits and wellness strategy.
• Manage compliance processes for HIPAA, ACA, ERISA.
• Build communication campaigns for employee education.

Skills

Strategic mindset

Analytical acumen

Communication skills

Leadership

Education

Bachelor’s degree

CEBS or similar certification

Tools

Workday

Excel

Job description

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 Managerto lead and elevate its self-funded benefits and wellness strategy.

You will be responsible forowning and modernizingemployee 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 strategyfor 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 strategythat 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 amentorand 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 programstied 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 complianceand U.S. regulations.

Analytical acumento track trends, optimize plans, and drive smart decisions.

Requirements

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

• Hands-on management ofself-funded health plansrequired.

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

• Experience supervisingbenefits 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 elevatethe 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.

Click here to apply online