Senior Compensation and Benefits Manager

Sterling St James LLC; Burr Ridge (IL); Hybrid; USD 100,000 - 120,000; Full time

Benefits offered by this job

Hybrid schedule

Medical, dental, vision coverage

Company-paid life and disability

401(k) with company match

Generous PTO and holidays

Job summary

Sterling St James LLC is seeking a seasoned Total Rewards Manager to own our benefits and retirement programs. You will lead Open Enrollment, manage the 401(k) plan, coordinate Form 5500 filings, and partner with leadership on plan design and vendor management.

The role requires deep expertise in ERISA, HIPAA, COBRA, ACA, FMLA, ADA, and related regulations, with a track record of owning comprehensive benefits functions. Hybrid work is available near Chicago’s southwest suburbs.

Qualifications

• Bachelor's degree required.
• Approximately 5+ years of progressive experience in Benefits/Total Rewards with ownership of employee benefits.
• Demonstrated success leading Open Enrollment from planning through execution.
• Strong experience administering 401(k) plans, coordinating Form 5500 filings, supporting 401(k) audits, and ensuring retirement plan compliance.
• Experience partnering on benefit plan design, renewals, and broker/vendor management.
• Experience supporting or leading 401(k) recordkeeper transitions or retirement plan conversions is a strong plus.
• Deep knowledge of FMLA, ADA accommodations, disability administration, and multi-state leave laws.
• Experience working with self-funded and/or fully insured health plans.
• HRIS experience, strong analytical skills, and the ability to confidently manage sensitive employee matters.

Responsibilities

• Lead all employee benefits programs across medical, dental, vision, life, disability, wellness, and voluntary benefits.
• Own the Open Enrollment process end-to-end from strategy to implementation.
• Partner with brokers and leadership on benefit plan design and vendor management.
• Manage all aspects of the company’s 401(k) plan including enrollment, vendor management, and compliance.
• Coordinate Form 5500 filings and support 401(k) audits and retirement plan compliance.
• Lead retirement plan initiatives including recordkeeper transitions and vendor conversions.
• Administer Leave of Absence programs including FMLA and multi-state leaves.
• Lead ADA reasonable accommodation processes with cross-functional partners.
• Develop employee communications and educational materials for benefits and retirement programs.
• Support employee recognition and reward programs.

Skills

Open Enrollment

401(k) administration

Form 5500 filings

Retirement plan design

FMLA & ADA administration

HRIS

Benefits leadership

Analytical skills

Multi-state leave laws

Education

Bachelor's degree

Job description

Total Rewards Manager

Hybrid | Chicago SW Suburbs | $100,000–$120,000 + Excellent Benefits

I’m partnering with a rapidly growing healthcare organization that’s looking for an experienced Total Rewards Manager to lead its benefits and retirement programs. This is a high-impact replacement opportunity for a seasoned professional who can take ownership of the company’s benefits function and serve as the internal expert on employee benefits, leave administration, retirement plans, and compliance.

This isn’t an HR generalist role. We’re looking for someone who has successfully led complex benefits programs and can confidently partner with leadership, employees, brokers, and vendors while ensuring compliance across a multi-state workforce.

What You’ll Own

• Lead all employee benefits programs, including medical, dental, vision, life, disability, wellness, and voluntary benefits.

• Own the annual Open Enrollment process from strategy and planning through vendor negotiations, employee communications, enrollment, and implementation.

• Partner with brokers and leadership on benefit plan design, evaluating plan offerings, recommending improvements, and helping deliver competitive, cost-effective programs.

• Manage all aspects of the company’s 401(k) plan, including participant communications, enrollment, vendor management, compliance, and ongoing administration.

• Coordinate Form 5500 filings, support annual 401(k) audits, and ensure retirement plan compliance.

• Help lead strategic retirement plan initiatives, including recordkeeper transitions and vendor conversions (experience with projects such as moving from Voya to Fidelity is highly desirable).

• Administer all Leave of Absence programs, including FMLA, Short-Term Disability, Long-Term Disability, military leave, paid family and medical leave programs, and multi-state leave requirements.

• Lead the ADA reasonable accommodation process, partnering with employees, managers, healthcare providers, and legal counsel to evaluate requests and ensure compliant workplace solutions.

• Develop employee communications and educational materials that simplify complex benefits and retirement programs.

• Support employee recognition and reward programs.

• Manage relationships with benefits brokers, retirement plan providers, insurance carriers, and third-party administrators.

• Ensure compliance with ERISA, HIPAA, COBRA, ACA, FMLA, ADA, and applicable federal and state regulations.

What We’re Looking For

• Bachelor’s degree required.

• Approximately 5+ years of progressive experience in Benefits, Total Rewards, or Human Resources, with significant ownership of employee benefits.

• Demonstrated success leading Open Enrollment from planning through execution.

• Strong experience administering 401(k) plans, coordinating Form 5500 filings, supporting 401(k) audits, and ensuring retirement plan compliance.

• Experience partnering on benefit plan design, renewals, and broker/vendor management.

• Experience supporting or leading 401(k) recordkeeper transitions or retirement plan conversions is a strong plus.

• Deep knowledge of FMLA, ADA accommodations, disability administration, and multi-state leave laws.

• Experience working with self-funded and/or fully insured health plans.

• HRIS experience, strong analytical skills, and the ability to confidently manage sensitive employee matters.

Most importantly, we’re looking for someone who has truly owned the benefits function. Whether you have five years or fifteen, we’re interested in candidates who have personally led Open Enrollment, managed retirement plans, coordinated Form 5500 filings and 401(k) audits, partnered on plan design, and administered complex leave and accommodation programs.

Why Consider This Opportunity?

• Compensation of $100,000–$120,000

• Hybrid schedule

• Comprehensive medical, dental, and vision coverage

• Company-paid life and disability insurance

• 401(k) with company match

• Generous PTO and paid holidays

• Join a growing healthcare organization where you’ll own a critical function, partner directly with leadership, and make a meaningful impact on employees across the company.

If you’re a seasoned Benefits or Total Rewards professional who enjoys ownership, strategic involvement, and solving complex employee benefit challenges, I’d welcome the opportunity to tell you more.