Director, Total Rewards

Jobtailor; Illinois; On-site; USD 180,000 - 280,000; Full time

Job summary

Jobtailor seeks a senior Total Rewards leader to evolve our compensation philosophy, job architecture, and pay structures. You will drive annual programs, market benchmarking, and pay equity analyses while ensuring regulatory compliance across a multi-site organization.

Lead health, welfare, and retirement benefits strategy, manage vendor partnerships, and oversee HRIS and analytics to enable data-driven decisions at the executive level.

Qualifications

• Bachelor’s degree in human resources, Business Administration, Finance, or related field, or equivalent

Responsibilities

• Develop and evolve compensation strategy including philosophy, architecture, pay structures, market pricing, governance
• Lead annual compensation programs including merit increases, incentive planning, and benchmarking
• Design and administer variable and incentive pay programs across frontline, corporate, and sales
• Conduct pay equity analyses and remediation approaches
• Ensure compliance with federal, state, and local regulations
• Develop and execute health, welfare, and retirement benefits strategy
• Oversee plan design, vendor partnerships, administration, compliance, renewal, and open enrollment
• Provide oversight of leave programs (FMLA, ADA, etc.)
• Build and evolve employee recognition strategy
• Provide oversight of HRIS capabilities, total rewards tech, and analytics
• Leverage AI-enabled insights for compensation, benefits, compliance, and decisions
• Develop total rewards reporting and dashboards for HR, Finance, executives
• Lead Total Rewards function and develop team capabilities
• Manage budgets; partner with brokers, Finance, HR, Operations and stakeholders
• Partner with Finance on cost modeling and forecasting
• Support total rewards integration for acquisitions
• Maintain plan documentation and audit readiness
• Deliver first-year objectives covering philosophy, architecture, salary structures, equity analysis, benefits renewal, and leave administration controls

Skills

Compensation Strategy

Total Rewards

Regulatory Knowledge

Analytical & Financial Modeling

People Leadership

Strategic Influence

Cross-functional Collaboration

Communication

Project Management

Data‑Driven Decision Making

Education

Bachelor’s degree in HR/Business/Finance

Eight+ years progressive experience in compensation/benefits/HR

Three+ years people leadership in total rewards

Tools

HRIS

Total Rewards Technology

Workforce Analytics

Job description

• Develop and evolve Pinnacle Live’s compensation strategy, including compensation philosophy, job architecture, pay structures, market pricing, and governance
• Lead annual compensation programs, including merit increases, incentive planning, and market benchmarking
• Design and administer variable and incentive pay programs across frontline, corporate, and sales populations
• Conduct pay equity analyses and develop remediation and governance approaches
• Ensure compliance with federal, state, and local compensation regulations
• Develop and execute health, welfare, and retirement benefits strategy
• Oversee plan design, vendor partnerships, administration, compliance, renewal, and open enrollment
• Provide strategic oversight of FMLA, ADA, state, local, and company leave programs
• Build and evolve an employee recognition strategy
• Provide strategic oversight of HRIS capabilities, total rewards technology, and workforce analytics
• Leverage AI-enabled insights for compensation, benefits, compliance, and data-driven decision-making
• Develop total rewards reporting and dashboards for HR, Finance, and executive leadership
• Lead the Total Rewards function and develop team capabilities
• Manage budgets and partner with brokers, vendors, Finance, HR, Operations, and other stakeholders
• Partner with Finance on cost modeling, accruals, and forecasting
• Support total rewards integration for acquisitions
• Maintain plan documentation, regulatory filings, and audit readiness
• Deliver first-year objectives including compensation philosophy, job architecture, salary structures, pay equity analysis, benefits renewal, leave administration controls, dashboards, and an employee recognition program

Requirements

• Bachelor’s degree in human resources, Business Administration, Finance, or a related field, or equivalent combination of education and directly related professional experience
• Eight or more years of progressive experience in compensation, benefits, HR operations, or total rewards
• Three or more years of direct people leadership experience managing and developing HR or total rewards staff
• Experience designing compensation programs, including compensation philosophy, job architecture, salary structures, market benchmarking, merit processes, and incentive programs
• Experience leading health, welfare, and retirement benefit programs end-to-end
• Working knowledge of ERISA, ACA, COBRA, HIPAA, FLSA, IRS Section 125, Form 5500, nondiscrimination testing, 401(k) governance, FMLA, ADA, and pay transparency and pay equity requirements
• Experience developing recommendations and presenting them to executive leadership
• Strong analytical and financial modeling skills
• Experience with data, technology, automation, and emerging tools for total rewards decision‑making
• Ability to influence leaders and build partnerships with Finance, HR, brokers, vendors, and business stakeholders
• Ability to balance enterprise consistency with the needs of a diverse, multi-site workforce
• Strong project management skills
• Ability to operate strategically while building processes, tools, and solutions
• Ability to explain complex compensation and benefits concepts clearly
• Sound judgment and discretion with confidential compensation data and protected health and personal information
• Ability to meet physical demands including sitting, standing or walking for long periods, bending, stooping, reaching, communicating, and occasionally lifting up to 50 pounds
• Extended business hours may be required

Core Competencies

Demonstrates expertise in developing and executing comprehensive compensation strategies, including job architecture, pay structures, and compliance with compensation regulations. Proven ability to lead total rewards functions, manage budgets, and leverage data‑driven insights for strategic decision‑making.

Highest-signal resume keywords

• Compensation Strategy Development
• Total Rewards Management
• Regulatory Compliance Knowledge
• Analytical and Financial Modeling Skills
• People Leadership Experience

ATS Optimization Keywords

Hard Skills

• Compensation Philosophy
• Job Architecture
• Market Benchmarking
• Incentive Program Design
• Health and Welfare Benefits Management
• Retirement Benefits Strategy
• Pay Equity Analysis
• Data‑Driven Decision‑Making
• Project Management
• Financial Modeling

Soft Skills

• Influencing Leaders
• Building Partnerships
• Clear Communication
• Sound Judgment
• Strategic Thinking

Industry Keywords

• ERISA
• ACA
• COBRA
• FLSA
• IRS Section 125
• Form 5500
• nondiscrimination testing
• 401(k) Governance
• FMLA
• ADA

Tools & Technologies

• HRIS Capabilities
• Total Rewards Technology
• Workforce Analytics
• AI‑Enabled Insights