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)