Director of Benefits

The Director of Benefits plays a critical leadership role in shaping and executing the organization’s total rewards and benefits strategy across the U.S. and Canada, with global collaboration responsibilities. This role oversees the design, administration, compliance, and optimization of health, welfare, and retirement programs while ensuring competitiveness, sustainability, and regulatory alignment.

This leader partners closely with HR, senior leadership, and regional teams to enhance employee wellbeing initiatives and drive strategic impact through effective benefits programming.

Key Responsibilities

Lead the annual review, design, and implementation of employee benefit programs, including vendor evaluation and budgeting

Oversee administration of health, welfare, and retirement plans across the U.S. and Canada

Manage vendor relationships and ensure service excellence and performance accountability

Direct and manage the annual benefits enrollment process

Develop and support global wellbeing initiatives in collaboration with regional teams

Ensure compliance with all applicable regulations (ACA, FMLA, ADA, COBRA, ERISA, HIPAA, and related legislation)

Monitor regulatory changes and assess impact on plan design and administration

Partner with HRIS, Payroll, and HR Operations on system updates, reporting, and data integrity

Supervise and mentor benefits team members

Research market trends and benchmark programs to maintain competitive positioning

Address escalated employee benefit matters with professionalism and discretion

Qualifications

Bachelor’s degree in Human Resources or related field required

Ability to be in office (downtown Chicago) three days a week

10+ years of progressive experience in benefits design and administration, including team leadership

Deep knowledge of health, welfare, and retirement plan management

Strong understanding of compliance requirements and regulatory frameworks

Experience working with HRIS systems (e.g., UKG, SuccessFactors or similar platforms)

Strong analytical, problem-solving, and communication skills

Demonstrated ability to manage multiple priorities in a fast-paced environment

High level of judgment, discretion, and confidentiality

Collaborative leadership style with strong stakeholder management capabilities