Steak n Shake · 9 hours ago
Director of Benefits
Steak ’n Shake offers the opportunity to lead benefits in a highly visible, impactful role within the HR organization. The Director of Benefits will lead the strategy, administration, and execution of benefits programs across a large, multi-state employee population, ensuring compliance and operational excellence.
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
Qualification
Required
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
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
Benefits
Medical
Dental
Vision
Life
Disability
Wellness
Voluntary benefits
401(k) retirement plan
Company
Steak n Shake
OUR VISION: Steak ‘n Shake is a classic American brand and we intend to lead and dominate the premium burger and milkshake segment of the restaurant industry.
Funding
Current Stage
Late StageTotal Funding
$225M2025-09-30Debt Financing· $225M
Recent News
2026-01-18
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