Director of People

Next Step Recruitment•Chicago, IL

31d•$120,000 - $150,000•Hybrid

About The Position

We are looking for a Director of People who is first and foremost an HR operator — someone who cares deeply about accuracy, compliance, systems, and making sure the organization runs cleanly and consistently as it scales. This is not a culture, recruiting, or program-building role. It is the operational backbone for a fast-moving, multi-state business where clean data, compliant processes, and precise execution matter every single day. This person will be the steady, detail-driven leader who keeps all people-related functions running correctly — payroll, benefits, HR systems, documentation, policies, audits, and regulatory compliance. You are someone who notices the small things, fixes them before they become big things, and sets up structures that prevent problems from recurring. You bring discipline to the function and hold the organization to a high operational standard. The Director of People will work closely with the executive team and directly support managers across the business. You will be trusted to tell the truth, flag risks early, and maintain a consistent, compliant foundation even as the business grows quickly and the pace stays high. This role plays a highly impactful part in the company's trajectory — not by building culture initiatives, but by ensuring the company’s people operations are reliable, compliant, and scalable. How This Role Fits Into the Team You will be the central owner of all HR operations , supported by finance, outside vendors, and administrative partners. The executive team relies on this role to: Keep the company out of risk Ensure payroll and benefits run correctly Maintain spotless systems and data Provide clear guidance to managers Build and enforce consistent policies Support growth by keeping the foundation solid You will partner most closely with: Finance – compensation cycles, headcount reporting, payroll alignment Operations leadership – performance documentation, ER support, compliance awareness CEO/COO – policy decisions, risk management, workforce planning This is a fit for someone who finds satisfaction in being the steady expert, the person who ensures nothing slips through the cracks, and who prefers structure, clarity, and predictability over ambiguity or culture programming. What This Role Is Not To ensure clarity: this is intentionally not a “people and culture” role. It is not : A recruiting-heavy role (minimal involvement; outsourced or handled by hiring managers) A culture transformation or engagement strategy role An L&D or talent development role A diversity, equity, and inclusion function A “build big programs from scratch” role If you prefer strategic culture work, high-visibility engagement programs, or talent acquisition ownership — this is not the right fit. If you prefer process, data, compliance, accuracy, and structure , this is the right fit. What Success Looks Like HR systems run cleanly with accurate and reliable data Payroll and benefits cycles are executed correctly and on time Policies are clear, updated, and consistently applied Managers receive precise guidance and follow it Federal, state, and local compliance is always in place Documentation is structured, timely, and audit-ready Leadership receives accurate dashboards and headcount reporting M&A activity is supported with clean due diligence and organized records The company can scale because the HR foundation is strong and stable

Requirements

10–15 years of HR operations, compliance, or people systems experience
Proven success in multi-state or multi-entity environments
Hands-on experience with HRIS implementation and optimization
Strong understanding of payroll cycles, benefits, compensation, and audits
Comfortable running a lean HR function with limited administrative support
Experience in regulated or high-volume industries (fintech, lending, ticketing, ecommerce, logistics, etc.)
High degree of business literacy and comfort working directly with executives
Values precision, consistency, and structured processes

Responsibilities

Maintain compliance with all federal, state, and local employment laws
Own HRIS administration (Workday, ADP, Rippling, Paylocity, or similar), including workflows, reporting, and data integrity
Oversee payroll and benefits administration; manage vendor relationships, audits, and renewals
Lead policy development, employee documentation, and performance-related processes
Partner with finance on compensation cycles, bonuses, and headcount forecasts
Provide compliance-focused guidance to managers on employee relations matters
Maintain accurate, audit-ready employee files and system records
Deliver clean HR analytics and dashboards to executive leadership
Support M&A or organizational transitions through due diligence readiness and structured integration processes
Maintain process consistency across multiple locations and legal jurisdictions