People Operations Manager Jobs in Chicago, IL
People Operations Manager jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, where technology firms, healthcare systems, and professional services companies drive consistent hiring demand. Employers posting roles right now include Grant Thornton, Huron Consulting, and The University of Chicago. Find a role that fits below and apply directly.
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WeDriveU is the leader in shared mobility solutions that connect communities, campuses, and workplaces. WeDriveU operates private shuttle and public transit systems across the U.S., serving millions of passenger journeys each year. The company's 5,500+ team members operate 4,000 vehicles across 55 U.S. locations, providing safe, reliable, and sustainable transportation solutions as part of a global family of brands serving more than 1 billion bus and rail passengers on four continents.
Position Summary
The Human Resources Business Partner will report to the VP of People and serve as a strategic and hands-on HR partner to WeDriveU operations in the Chicago market. This role requires strong, demonstrated labor relations experience in a unionized environment. The HRBP will work closely with operational leaders, employees, shop stewards, union representatives, and the broader People team to manage employee and labor relations matters, administer collective bargaining agreements, resolve grievances, conduct investigations, and provide practical HR guidance that supports both the business and our employees.
The successful candidate will be comfortable operating independently in a fast-paced, high-volume environment and will bring the judgment, credibility, and labor relations experience needed to advise leaders on complex and sensitive workforce matters.
Essential Responsibilities
Serve as the primary HR business partner to assigned Chicago operations, providing hands-on employee and labor relations support in a unionized environment.
Build strong, trusted relationships with operational leaders, employees, shop stewards, union representatives, and business agents.
Interpret and administer collective bargaining agreements and advise management on consistent application of contract provisions, company policies, established practices, and applicable employment laws.
Manage the grievance process from initial filing through resolution, including investigating allegations, gathering documentation, preparing management responses, participating in grievance meetings, and supporting arbitration preparation when necessary.
Advise leaders on employee relations matters including attendance, performance management, progressive discipline, suspensions, terminations, workplace conduct, and other corrective actions, with appropriate consideration of CBA requirements and past practices.
Conduct effective, thorough, timely, and objective workplace investigations involving employee complaints, policy violations, harassment, discrimination, retaliation, workplace conduct, and other employee relations concerns.
Partner with Employee & Labor Relations and Legal on escalated grievances, arbitration matters, unfair labor practice issues, bargaining-related matters, and other complex employee relations concerns.
Coach and advise managers on documentation, performance expectations, corrective action, employee relations practices, and effective labor-management relationships.
Maintain in-depth knowledge of federal, state, and local employment requirements and provide guidance that reduces risk and supports consistent HR practices.
Identify employee and labor relations trends and recommend practical solutions to improve engagement, retention, productivity, and operational effectiveness.
Ensure employee relations and labor matters are documented appropriately and followed through to resolution with clear and timely communication to employees and leaders.
Partner with leaders on organizational and workforce matters, including staffing challenges, employee engagement, retention, change management, and other business needs.
Use workforce data and HR metrics to identify trends, support recommendations, and help leaders make informed people decisions.
Support HR projects, policy implementation, training initiatives, and other People team priorities as needed.
Additional duties and responsibilities may apply based on business needs.
Required Qualifications
5+ years of progressive Human Resources experience, preferably in an HR Business Partner, Employee Relations, or Labor Relations role.
Demonstrated experience supporting unionized employee populations.
Hands-on experience administering collective bargaining agreements and managing grievances.
Experience working directly with union representatives, business agents, and shop stewards.
Strong experience advising leaders on employee relations, investigations, progressive discipline, performance management, and terminations.
Strong working knowledge of federal and state employment laws, wage and hour requirements, the National Labor Relations Act, and labor-management practices.
Ability to independently manage sensitive, complex, and high-volume employee and labor relations matters with sound judgment and discretion.
Strong written and verbal communication skills with the ability to influence, coach, and advise leaders at multiple levels of the organization.
Strong organizational and analytical skills with the ability to manage multiple priorities and follow matters through to completion.
Proficiency with HR systems, Microsoft Excel/Google Sheets, and Google Workspace.
Preferred Qualifications
Bachelor's degree in Human Resources, Business Administration, Labor Relations, or a related field.
Experience supporting a high-volume, hourly workforce in transportation, transit, logistics, manufacturing, distribution, or a similar operational environment.
Experience preparing grievance responses and supporting arbitration matters.
Experience partnering with field operations across multiple locations or business units.
PHR/SPHR, SHRM-CP/SHRM-SCP, or other relevant HR or labor relations certification.
What We Offer
Physical Health: Exceptional Medical, Dental, Vision, and Life Insurance benefits.
Financial Health: Competitive compensation packages, 401(k) with 4% employer match, Financial Wellness Tool, and Commuter Benefits.
Emotional Health: Employee Assistance Program (EAP), PTO for part-time and full-time positions, paid holidays, and Pet & Legal Insurance.
Personal Development: On-the-job training and skills development, and internal transfer opportunities for career growth.
Benefits vary by position and location.
Additional Terms and Company Statements
Physical Requirements
The physical requirements of this position include the ability to perform work in a professional office or remote-work environment, use a computer and other standard office equipment, communicate effectively in person and through electronic platforms, and participate in meetings for extended periods. Reasonable accommodations may be provided to qualified individuals with disabilities.
Equal Employment Opportunity
WeDriveU is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment free of discrimination or harassment where the thoughts and ideas of all employees are appreciated and respected. We value excellence and recognize that respecting the diverse backgrounds, skills, and perspectives of our workforce helps us attract, retain, and develop the best talent available.
Reasonable Accommodation
Applicants who require a reasonable accommodation during the application or interview process should contact WeDriveU's Human Resources team.
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Top Industries Hiring
- Automotive
- Accounting & Auditing
- Chemicals & Materials
- Consulting & Professional Services
People Operations Manager Jobs in Chicago: Frequently Asked Questions
How do I get a people operations manager job in Chicago?
Focus your search on Chicago's Loop, Fulton Market, and River North districts, where technology companies, financial services firms, and healthcare organizations concentrate their HR teams. Candidates with experience in HRIS implementation, workforce planning, or DEI program management stand out in this market. Networking through local SHRM Chicago chapter events and targeting mid-size tech and fintech employers that are actively scaling also gives applicants a meaningful edge.
Which companies hire people operations managers in Chicago?
Chicago people operations manager roles are posted by Grant Thornton, Huron Consulting, and The University of Chicago and others right now, based on current listings on Migrate Mate as of August 2026. Chicago's employer mix includes large enterprise companies headquartered downtown, fast-growing tech and healthtech startups in Fulton Market, and professional services firms that maintain sizable people operations teams across the metro area.
Are there remote people operations manager jobs in Chicago?
Yes, though remote availability depends on the role's scope, since people operations managers who handle employee relations, onboarding, and in-office culture programs typically work on-site, while those focused on HR analytics, systems, or policy tend to work remotely more often. About 61% of people operations manager openings tied to Chicago are remote or hybrid as of August 2026, with hybrid arrangements most common among Chicago's technology and professional services employers.
How can I get a people operations manager job in Chicago with little or no experience?
The most realistic entry path in Chicago is moving into a people operations manager role from an HR coordinator or HR generalist position at a mid-size Chicago company, particularly in the technology, healthcare, or nonprofit sectors that tend to develop internal talent. Roles at Chicago-area hospital systems, university administrative offices, or growing Fulton Market startups often promote from within, and building experience with HRIS platforms like Workday or BambooHR makes candidates significantly more competitive for that first manager-level opening.
Which industries hire the most people operations managers in Chicago?
The sectors hiring the most people operations managers in Chicago are Automotive, Accounting & Auditing, and Chemicals & Materials, based on current listings on Migrate Mate as of August 2026. Chicago's status as a hub for enterprise technology, financial services, and major healthcare systems means these industries maintain large, dedicated people operations functions that regularly open manager-level positions.
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