Director, People Operations

With more than 25 years in business, The Parking Spot has grown into the largest near-airport parking company in the United States with over 2,000 valued team members across over 40 locations nationwide. We are proud to offer an Employee Ownership Program, allowing every team member the opportunity to receive a direct financial stake in The Parking Spot’s success. As employee owners, every one of us plays a part in providing exceptional service to our guests across the country.

What makes working at The Parking Spot so special? We’ve built a culture of support, fun, and camaraderie that empowers us to be the most innovative company in the parking industry. As a nationwide business with a small business feel, there are endless opportunities within The Parking Spot to grow your career. Come join us and see how we leverage people and technology to deliver a superior product, outshine our competition, and find creative and innovative solutions to everyday problems.

Salary Range: $160,000 per year - $165,000 per year

What we offer:

• 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

Position Summary:

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.

Key Responsibilities:

*People Operations and Talent Acquisition*

- 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

*Compliance and Risk Management:*

• 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

People Systems, Data, and Automation

• 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

*Core People Processes and Programs*

- 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

Knowledge, Skills & Experience Required:

• 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 (union and non-union preferred)
• Background in transportation, hospitality, retail, or in a complex, decentralized operations preferred
• 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

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*Any disclosed pay range is based on a consideration of neutral factors and criteria such as required qualifications, experience, education, skill, training, certifications, seniority, etc. The Parking Spot reserves the right to offer the selected candidate or applicant a salary at an appropriate level to be set and determined by the employer that is commensurate with the applicant’s qualifications, experience, education, skill, training, certifications, or seniority.*

At The Parking Spot, we don’t just accept difference - we celebrate and seek it.
We believe a diverse, inclusive, and equitable company is one where all employees, partners, and customers are welcome, supported, and valued. As a company in the travel industry, we witness the power of bringing individuals from different backgrounds and communities together. We treat all others with dignity and respect and stand firmly against racism and discrimination in any form. We intentionally develop diverse teams and relationships to ensure all voices are heard and to foster equal opportunity for all. We are committed to listening, learning, and growing because we know that our work is never done.