Fractional General Counsel

Montway Auto Transport is seeking a fractional General Counsel to provide broad legal coverage across its operations. The role spans litigation management in state and federal courts, drafting and negotiating a wide range of commercial contracts, overseeing an insurance portfolio, advising on regulatory and employment matters across multiple jurisdictions, and supporting M&A and financial transactions. The attorney will manage outside counsel, handle discovery and dispute resolution, and keep internal policies current with changing laws.

This is a part-time engagement with the option to transition to a full-time position at a future date. Applicants with a background in transportation or SaaS sectors are particularly encouraged to apply.

• Represent the company in state, federal, administrative, and appellate proceedings, including pro hac vice appearances as required
• Draft, review, and negotiate a broad range of commercial agreements including service, SaaS, employment, and settlement contracts
• Oversee the company's insurance portfolio, manage claims, negotiate renewals, and ensure certificate and contract compliance
• Research and advise on federal and state regulations affecting transport operations, and update internal policies accordingly
• Counsel HR on labour laws across multiple jurisdictions and maintain the company handbook
• Support M&A activity, debt and equity transactions, and due diligence processes in collaboration with senior management and outside counsel

• Law degree and current membership in good standing with the Illinois Bar Association
• Three to five years of legal experience, preferably in transportation or SaaS sectors
• Demonstrated ability to manage litigation, contracts, and regulatory matters independently
• Strong drafting, research, and written communication skills with close attention to detail
• Ability to manage multiple priorities and deliver results in a fast-paced, deadline-driven environment
• Self-motivated with a professional demeanour and effective interpersonal skills

Montway Auto Transport is one of the leading vehicle shipping companies in the United States, recognised by Inc. Magazine as one of the fastest-growing businesses nationally and certified as a Great Place to Work. The company has facilitated the safe transport of over 1.8 million vehicles, combining logistics technology with personalised customer service.