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

• 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

• 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

• Chicago, IL

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