About the Role

Steak ’n Shake is seeking a Director of Benefits to lead the strategy, administration, and execution of our benefits programs across a large, multi-state employee population. This role reports directly to the Vice President of Human Resources, serves as a member of the HR Leadership Team, and manages one internal direct report.

This position is ideal for a benefits leader who enjoys both strategic ownership and hands-on execution—someone comfortable rolling up their sleeves while shaping programs that directly impact employees’ lives.

Key Responsibilities

Benefits Strategy & Administration

• Own the design, delivery, and day-to-day administration of all employee benefit programs, including medical, dental, vision, life, disability, wellness, and voluntary benefits
• Evaluate benefit offerings regularly to ensure competitiveness, cost effectiveness, and alignment with company goals

Open Enrollment

• Lead annual open enrollment from end to end, including planning, vendor coordination, communications, system setup, and post-enrollment reconciliation
• Ensure a smooth, accurate, and employee-friendly enrollment experience

Compliance & Governance

• Oversee ACA compliance and reporting, including vendor coordination and regulatory deadlines
• Manage 401(k) retirement plan governance, including vendor oversight, audits, and fiduciary compliance
• Administer and ensure compliance with FMLA, ADA, and state-specific leave laws
• Maintain compliance across multiple states and jurisdictions

Vendor Management

• Serve as primary point of contact for benefits brokers, insurance carriers, third-party administrators, and retirement plan vendors
• Lead renewals, RFPs, contract negotiations, and ongoing performance management

Operational Excellence & Leadership

• Provide day-to-day leadership and development for one internal direct report
• Maintain accurate benefits data, documentation, and reporting
• Troubleshoot escalated employee issues and complex benefit cases
• Partner closely with HR leadership, finance, legal, and operations teams to improve processes, controls, and systems

Minimum Qualifications

• Bachelor’s degree in Human Resources, Business Administration, or a related field (or equivalent experience)
• 7+ years of progressive experience in employee benefits administration and compliance
• Demonstrated ownership of open enrollment execution in a multi-state environment
• Strong working knowledge of ACA compliance and reporting
• Hands-on experience administering 401(k) retirement plans
• Practical experience with FMLA, ADA, and state-specific leave laws
• Proven experience managing external vendors (brokers, carriers, TPAs)
• Ability and willingness to perform detailed, operational work in addition to strategic leadership

Preferred Qualifications

• 10+ years of benefits experience, including leadership responsibility
• Experience supporting a large, distributed, hourly workforce across multiple states
• Prior experience in retail, hospitality, restaurant, or similarly complex operating environments
• Professional certifications such as CEBS, SHRM-CP/SHRM-SCP, or SPHR
• Experience leading benefits through periods of growth, change, or transformation
• Strong data, audit, and reporting orientation

Competencies & Work Style

• Self-starter who works independently and takes ownership
• Highly detail-oriented with strong follow-through
• Thrives in a fast-paced, ever-changing environment
• Comfortable getting “in the weeds” with day-to-day work—this is not a purely advisory role
• Practical, solutions-oriented mindset with strong judgment

Why Steak ’n Shake

Steak ’n Shake offers the opportunity to lead benefits in a highly visible, impactful role within the HR organization. As a member of the HR Leadership Team, you will help shape programs that directly affect employees across the country while partnering closely with senior leadership.

#Corp7080

About the Role

Steak ’n Shake is seeking a Director of Benefits to lead the strategy, administration, and execution of our benefits programs across a large, multi-state employee population. This role reports directly to the Vice President of Human Resources, serves as a member of the HR Leadership Team, and manages one internal direct report.

This position is ideal for a benefits leader who enjoys both strategic ownership and hands-on execution—someone comfortable rolling up their sleeves while shaping programs that directly impact employees’ lives.

Key Responsibilities

Benefits Strategy & Administration

• Own the design, delivery, and day-to-day administration of all employee benefit programs, including medical, dental, vision, life, disability, wellness, and voluntary benefits
• Evaluate benefit offerings regularly to ensure competitiveness, cost effectiveness, and alignment with company goals

Open Enrollment

• Lead annual open enrollment from end to end, including planning, vendor coordination, communications, system setup, and post-enrollment reconciliation
• Ensure a smooth, accurate, and employee-friendly enrollment experience

Compliance & Governance

• Oversee ACA compliance and reporting, including vendor coordination and regulatory deadlines
• Manage 401(k) retirement plan governance, including vendor oversight, audits, and fiduciary compliance
• Administer and ensure compliance with FMLA, ADA, and state-specific leave laws
• Maintain compliance across multiple states and jurisdictions

Vendor Management

• Serve as primary point of contact for benefits brokers, insurance carriers, third-party administrators, and retirement plan vendors
• Lead renewals, RFPs, contract negotiations, and ongoing performance management

Operational Excellence & Leadership

• Provide day-to-day leadership and development for one internal direct report
• Maintain accurate benefits data, documentation, and reporting
• Troubleshoot escalated employee issues and complex benefit cases
• Partner closely with HR leadership, finance, legal, and operations teams to improve processes, controls, and systems

Minimum Qualifications

• Bachelor’s degree in Human Resources, Business Administration, or a related field (or equivalent experience)
• 7+ years of progressive experience in employee benefits administration and compliance
• Demonstrated ownership of open enrollment execution in a multi-state environment
• Strong working knowledge of ACA compliance and reporting
• Hands-on experience administering 401(k) retirement plans
• Practical experience with FMLA, ADA, and state-specific leave laws
• Proven experience managing external vendors (brokers, carriers, TPAs)
• Ability and willingness to perform detailed, operational work in addition to strategic leadership

Preferred Qualifications

• 10+ years of benefits experience, including leadership responsibility
• Experience supporting a large, distributed, hourly workforce across multiple states
• Prior experience in retail, hospitality, restaurant, or similarly complex operating environments
• Professional certifications such as CEBS, SHRM-CP/SHRM-SCP, or SPHR
• Experience leading benefits through periods of growth, change, or transformation
• Strong data, audit, and reporting orientation

Competencies & Work Style

• Self-starter who works independently and takes ownership
• Highly detail-oriented with strong follow-through
• Thrives in a fast-paced, ever-changing environment
• Comfortable getting “in the weeds” with day-to-day work—this is not a purely advisory role
• Practical, solutions-oriented mindset with strong judgment

Why Steak ’n Shake

Steak ’n Shake offers the opportunity to lead benefits in a highly visible, impactful role within the HR organization. As a member of the HR Leadership Team, you will help shape programs that directly affect employees across the country while partnering closely with senior leadership.

#Corp7080