Director, People Operations

The Parking Spot • Chicago, IL

2d • $160,000 - $165,000 • Hybrid

About The Position

The Director of People Operations is a key leader responsible for building a scalable, high-impact people function that supports the company’s continued growth. This role oversees talent acquisition, employee relations, and field operations, ensuring that core people processes operate effectively while evolving toward a more efficient, data-driven operating model. This leader will modernize People Operations by standardizing processes, embedding automation, and leveraging AI-enabled tools to reduce manual effort, improve accuracy, and enhance the employee and candidate experience. The Director serves as a strategic partner and coach to leaders across the organization, helping navigate complex employee matters with sound judgment and practical solutions. Based in our Chicago office, this is a high-impact opportunity to shape the future of the HR function during a period of department transformation.

Requirements

• 8+ years of progressive Human Resources experience, with at least 3+ years in a leadership role managing teams
• Experience supporting a multi-state, high-volume hiring frontline workforce
• Strong business acumen with the ability to connect people strategy to operational and financial outcomes
• Proven ability to lead through growth, change, and operational complexity
• Deep expertise across HR disciplines, including employee relations, talent acquisition, compliance, and HR systems
• Experience leveraging HR technology, automation, and data analytics to drive results
• Ability to operate both strategically and hands-on, with strong execution and problem-solving skills
• Excellent communication and relationship-building skills across all levels of the organization
• Ability to manage competing priorities and remain effective in a fast-paced, evolving environment
• Willingness to travel quarterly and as-needed for market visits, acquisitions, and company events

Nice To Haves

• Experience supporting a multi-state, high-volume hiring frontline workforce (union and non-union preferred)
• Background in transportation, hospitality, retail, or in a complex, decentralized operations preferred

Responsibilities

• Lead and develop the People Operations function, including Talent Acquisition, HR Business Partners, and employee lifecycle processes
• Partner with senior leadership to align people strategies with business objectives, growth plans, and operational needs
• Drive a culture of accountability, responsiveness, and service across the HR team
• Oversee Talent Acquisition strategy, including automation, sourcing optimization, and funnel performance (KPIs)
• Drive innovation in recruiting through AI tools, programmatic sourcing, and diversified channels
• Partner with operations leaders on workforce planning and hiring forecasts
• Improve candidate experience and conversion rates across the hiring lifecycle
• Direct the HR Business Partner team in supporting field operations, including employee relations, performance management, and organizational effectiveness
• Provide guidance on complex employee and labor matters, partnering with the Chief People Officer and Legal as needed
• Ensure consistent, fair, and compliant practices across all locations
• Build strong relationships with field leadership and frontline teams to maintain trust and engagement
• Ensure compliance with federal, state, and local employment laws, including FLSA, wage and hour, pay transparency, and leave programs
• Oversee DOT-related compliance (driver qualification files, medical certifications, drug and alcohol testing, Clearinghouse requirements)
• Develop and maintain a company-wide audit program to ensure consistent compliance across all locations
• Partner with Legal and the Chief People Officer on labor matters, including investigations, grievances, and contract administration as applicable
• Utilize HR technology platforms (e.g., UKG, Paradox, First Advantage, Navex, Awardco) to drive efficiency and insight
• Partner with HRIS and People Analytics to operationalize AI and automation, improving workflows and data accuracy
• Lead system adoption efforts by promoting full utilization and removing obstacles that hinder effective use across the organization
• Strengthen HR’s capability as a data-driven business partner through reporting and analytics
• Lead and continuously improve performance management and compensation cycles
• Oversee employee engagement initiatives, including surveys, communications, and action planning
• Partner on employee experience and recognition programs to drive retention and engagement
• Deliver regular reporting and insights on turnover, retention, employee relations trends, and recruiting performance
• Identify trends and develop action plans related to labor cost, turnover, and workforce effectiveness

Benefits

• Participation in and financial benefit from our shared employee ownership program
• Hybrid work experience in downtown Chicago
• Career development and growth opportunities
• Ability to gain exposure to all areas of the business
• Great benefits including Medical, Vision, Dental and a 401k plan
• Annual discretionary bonus program
• Team oriented, fun and friendly work environment
• Immediate opportunity to make a large impact

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 251-500 employees