Director of Benefits

Director of Benefits San Antonio Corporate - 3.1 San Antonio, TX Job Details Full-time 1 day ago Benefits Dental insurance Qualifications Affordable Care Act (ACA) Defined contribution retirement plans Benefits strategy management FMLA Regulatory compliance HR legal compliance Vendor relationship management Strategic thinking in HR leadership Full Job Description 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 INDHEADOFFICE