Director of People

The Director of People will oversee HR operations, systems, and compliance across a growing, multi-state organization operating in a high-volume, transaction-driven industry. This person ensures accuracy, consistency, and compliance across every people-related process—from payroll and benefits to performance documentation and HR system data integrity.

The ideal candidate is an HR operations leader with both strategic and hands-on capability —someone who has scaled people systems and processes within a fast-paced, regulated business. They bring rigor, structure, and efficiency to HR programs without leaning into recruiting or culture-building initiatives.

The environment is fast-moving, performance-driven, and data-centric. Success in this role means keeping the organization fully compliant and operationally sharp while building reliable systems that support rapid growth.

Compensation : $120,000–$150,000 base, with flexibility for exceptional experience

Key Responsibilities

Maintain compliance with all federal, state, and local employment laws

Own HRIS administration (Workday, ADP, Rippling, or similar), including reporting, workflows, and system improvements

Oversee payroll and benefits administration; manage vendor relationships and audits

Lead policy development, employee documentation, and performance processes

Partner with finance on compensation cycles, merit / bonus planning, and headcount reporting

Advise managers on employee relations and compliance-sensitive matters

Manage data accuracy and HR analytics, providing reliable dashboards for leadership

Support M&A or organizational transitions by maintaining HR due diligence and integration readiness

Preferred Background

10–15 years of experience in HR operations, compliance, or people systems , with increasing responsibility

Proven success managing multi-entity or multi-state compliance

Experience with HRIS implementation and optimization (e.g., Workday, Rippling, ADP, Paylocity)

Skilled in compensation and benefits administration, audits, and workforce reporting

Comfortable leading a small HR team or function in a lean, high-performance environment

Prior exposure to regulated or transaction-heavy sectors such as fintech, lending, ticketing, or ecommerce

Strong executive partnership and business acumen—able to communicate with clarity and precision

Location

Chicago, IL

In-office / hybrid (minimum 4 days per week)

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