Director of Benefits

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 benefitsEvaluate benefit offerings regularly to ensure competitiveness, cost effectiveness, and alignment with company goalsOpen Enrollment

Lead annual open enrollment from end to end, including planning, vendor coordination, communications, system setup, and post-enrollment reconciliationEnsure a smooth, accurate, and employee-friendly enrollment experienceCompliance & Governance

Oversee ACA compliance and reporting, including vendor coordination and regulatory deadlinesManage 401(k) retirement plan governance, including vendor oversight, audits, and fiduciary complianceAdminister and ensure compliance with FMLA, ADA, and state-specific leave lawsMaintain compliance across multiple states and jurisdictionsVendor Management

Serve as primary point of contact for benefits brokers, insurance carriers, third-party administrators, and retirement plan vendorsLead renewals, RFPs, contract negotiations, and ongoing performance managementOperational Excellence & Leadership

Provide day-to-day leadership and development for one internal direct reportMaintain accurate benefits data, documentation, and reportingTroubleshoot escalated employee issues and complex benefit casesPartner closely with HR leadership, finance, legal, and operations teams to improve processes, controls, and systemsMinimum 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 complianceDemonstrated ownership of open enrollment execution in a multi-state environmentStrong working knowledge of ACA compliance and reportingHands-on experience administering 401(k) retirement plansPractical experience with FMLA, ADA, and state-specific leave lawsProven experience managing external vendors (brokers, carriers, TPAs)Ability and willingness to perform detailed, operational work in addition to strategic leadershipPreferred Qualifications

10+ years of benefits experience, including leadership responsibilityExperience supporting a large, distributed, hourly workforce across multiple statesPrior experience in retail, hospitality, restaurant, or similarly complex operating environmentsProfessional certifications such as CEBS, SHRM-CP/SHRM-SCP, or SPHRExperience leading benefits through periods of growth, change, or transformationStrong data, audit, and reporting orientationCompetencies & Work Style

Self-starter who works independently and takes ownershipHighly detail-oriented with strong follow-throughThrives in a fast-paced, ever-changing environmentComfortable getting “in the weeds” with day-to-day work—this is not a purely advisory rolePractical, solutions-oriented mindset with strong judgmentWhy 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.

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Compensation: Competitive salary