Corporate Lawyer – Employment Law

Founded in 2012 by Steve Gold and headquartered in Chicago, 160 Driving Academy is the nation's largest training provider and job creator for commercial drivers in the United States. 160's 151 Commercial Driving Schools are licensed and compliant in the 44 states where it operates and with the Federal Motor Carrier Safety Administration (FMCSA). As the largest supplier of human capital to the transportation industry, 160 plans to have 200 Commercial Driving Schools opened by 2026 and train over 50,000 drivers.

We are an innovative leading organization within the trucking industry, encompassing education, networking, and safety evaluation services through our brands—160 Driving Academy, Truckers Network, and 160 Score.

Location: Chicago, IL (Corporate Headquarters) 

Job Summary: 

We are seeking an experienced and proactive Corporate Lawyer specializing in employment law to join our Chicago-based corporate headquarters. In this role, you will oversee all general employment legal matters for our 152 CDL training academies across the United States. Your expertise will help ensure compliance with federal and state employment laws, mitigate legal risks, and support the growth and success of our organization. 

Key Responsibilities: 

• Provide legal counsel on employment matters, including hiring practices, contracts, terminations, benefits, workplace policies, and compliance with federal, state, and local labor laws. 

• Draft, review, and negotiate employment agreements, contracts, and internal policies to ensure legal and organizational compliance. 

• Handle employee disputes, investigations, and grievances, working closely with HR teams across all academies to resolve issues effectively. 

• Advise on legal risks related to employment practices and recommend proactive strategies to mitigate risks. 

• Ensure compliance with labor laws, including FLSA, OSHA, EEOC regulations, and other applicable employment statutes. 

• Represent the company in legal proceedings, including mediations, arbitrations, and litigation, as needed. 

• Stay updated on changes in employment laws and regulations across the United States and provide training to HR and leadership teams. 

• Collaborate with external legal counsel when necessary to manage complex cases or specialized matters. 

• Support corporate initiatives by providing legal advice on strategic decisions impacting the workforce. 

Qualifications: 

• Juris Doctor (JD) from an accredited law school and active bar membership in Illinois (additional state bar memberships a plus).  

• Preferably 5 years of experience in employment law, preferably in a corporate or multi-location environment. 

• Strong knowledge of federal and state labor laws, regulations, and employment-related compliance. 

• Proven experience handling employee relations, disputes, and contract negotiations. 

• Excellent analytical and problem-solving skills with a strong attention to detail. 

• Exceptional communication and interpersonal skills to effectively advise HR teams and leadership. 

• Ability to manage multiple priorities in a fast-paced environment while maintaining a proactive approach. 

• Familiarity with the transportation or vocational training industry is a plus but not required. 

Why Join Us? 

• Be part of a growing organization that is transforming the commercial driving industry. 

• Competitive salary with comprehensive benefits, including health insurance, retirement plans, and performance-based incentives. 

• Opportunity to shape the legal framework of a nationwide company with a meaningful mission. 

• Collaborative work environment at our corporate headquarters in Chicago. 

• Potential for professional growth as part of a dynamic and innovative team.