Crucial Hire
Benefits Manager to
Lead 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 a
hands-on, strategic Benefits Manager
to lead and elevate its self-funded benefits and wellness strategy. You will be responsible for
owning 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 true
player-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 a
strategic leadership opportunity
. The company is evolving rapidly and needs a benefits leader who can: Drive smarter outcomes in health and wellbeing programs . Redesign the wellness strategy for 2025 and beyond. Ensure compliance strength for self-funded plans . Build a better benefits experience that supports employee retention, satisfaction, and organizational health . If you want to make a
visible impact
— this is your opportunity to shine. What You’ll Own & Lead Strategic Benefits Management Modernize and manage self-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 a data-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 that translate complex benefits into clear, engaging education . Create a better onboarding and total compensation education experience for employees. Leadership & Culture Building Supervise a Benefits & Leave Specialist, serving as a mentor 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 of self-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 like Workday 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 to own 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.
Click here to apply online #J-18808-Ljbffr
Lead 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 a
hands-on, strategic Benefits Manager
to lead and elevate its self-funded benefits and wellness strategy. You will be responsible for
owning 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 true
player-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 a
strategic leadership opportunity
. The company is evolving rapidly and needs a benefits leader who can: Drive smarter outcomes in health and wellbeing programs . Redesign the wellness strategy for 2025 and beyond. Ensure compliance strength for self-funded plans . Build a better benefits experience that supports employee retention, satisfaction, and organizational health . If you want to make a
visible impact
— this is your opportunity to shine. What You’ll Own & Lead Strategic Benefits Management Modernize and manage self-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 a data-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 that translate complex benefits into clear, engaging education . Create a better onboarding and total compensation education experience for employees. Leadership & Culture Building Supervise a Benefits & Leave Specialist, serving as a mentor 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 of self-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 like Workday 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 to own 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.
Click here to apply online #J-18808-Ljbffr