A Transportation Law Firm

Cassandra K. Gaines, Esq

Cassandra has significant legal experience in the transportation industry both as in-house counsel for some of the largest transportation companies in the industry and as a transportation litigator at a nationwide law firm. Cassandra prides herself on keeping pace with the quickly changing industry and helping her clients stay ahead of legal issues just around the corner.


Cassandra is the founding partner of a boutique transportation law firm and consulting group dedicated to transforming legal service in the industry. Prior to establishing her law firm, Cassandra served as the Associate General Counsel of Claims and Litigation at Schneider National Inc. Cassandra not only led a team of adjusters at Schneider but was responsible for the legal outcome of all claims and litigation arising from the transportation of goods. She managed hundreds of lawsuits and attorneys across the country and developed a unique understanding of litigation trends and strategies in the transportation industry.


Prior to Schneider, Cassandra worked for one of the largest transportation brokerages in the industry, Echo Global Logistics Inc., where she was the lead in-house attorney and Director of Cargo Security. At Echo, Cassandra built a legal department, developed a contract management program, and managed a carrier-compliance department. She was responsible for reducing cargo theft, during a time in which the industry was plagued with theft across the country.


Prior to going in-house, Cassandra was a transportation litigator at a nationwide law firm. During that time, she gained experience representing trucking and logistics companies in litigation, contract negotiation, cargo claims, unpaid freight charges and risk management matters.


Cassandra’s legal practice is enhanced by her prior business experience in New York City at two Fortune 500 companies, where she gained a wide range of experience in sales, marketing, operations (including wholesale and distribution) and management. Cassandra’s holds a Bachelor’s Degree in Economics and Financial management from Cornell University. She received her law degree from University of California, Hastings College of Law.

Transportation Lawyer for Modern Companies

Cassandra Gaines is an entrepreneur, transportation law expert and transportation industry influencer. She was recently named one of the 100 People Transforming Business in North America by Business Insider joining alumni such Elon Musk, Jack Dorsey, and Jeff Bezos. Cassandra has disrupted the transportation industry with a lively Joe Rogan-like show called “MadGaines Live” where each month, over 250,000 loyal viewers from across all social media platforms tune in to her educational, non-traditional show where she unites a very fragmented, volatile industry.

MadGaines Live is Every Friday at 2pm CST (Chicago Time) on all social media platforms.


Contract Review, Drafting and Negotiating

GLG has extensive experience in drafting, negotiating and revising contracts specific to the transportation industry. A few examples of such contracts include broker-carrier and shipper-broker agreements, managed transportation transactions, agent agreements, website terms and conditions, shipper-carrier agreements, interchange, tariffs, NDAs, and user agreements.

Cargo Claim Assessment and Resolution

Insurers and carriers often dispute claims with brokers or there is a lack of insurance coverage. GLG has the experience to efficiently handle the cargo claim dispute and bring the dispute to resolution. GLG has an intricate understanding of the surrounding legal landscape including the federal statute, the Carmack Amendment, and Title 49 of the Code of Federal Regulations (49 CFR).

Claims Management Enhancement

Set your company apart with a robust claims management program and enhance your claims personnels’ knowledge through legal fundamentals and business negotiation techniques. Utilize leading technology to automate the claims process and increase operational efficiencies. Prevent cargo claims with predictive analytics, enhanced internal procedures designed to be a stop-gate for common occurrences that give rise to cargo claims and proactive measures that increase processing speed.

Cargo Theft and Carrier Fraud Avoidance

Fraud and theft not only costs your company money but also destroys customer relationships. We work to protect your company against such occurrences, train sales and compliance departments and implement anti-fraud/theft work practices. Such efforts will enhance your personnels’ industry knowledge but will provide your sales representatives with a selling point for customers concerned with industry fraud and theft.

Contract Management Improvement

Increase your contract review time, ensure edits are both strategic and necessary, and understand the key risks to your business. GLG has a unique contract management program for clients that includes a combination of legal training, leadership skills, productivity considerations, and smart decision making. Creating and approving contracts with an acceptable risk should be an easy process unique to each business, so that deals are closed efficiently.

Insurance Coverage Assessment and Training

GLG provides audit services to identify gaps in insurance coverage and a training program to help key personnel better understand what risks are covered by insurance and what risks are not. In addition, GLG has designed a specific program for compliance departments to better ensure third-party carriers have the appropriate insurance for certain commodities and shippers.

Risk Management Assessment and Training

It is a common theme that a broker will eventually hit a tipping point in their business where the risks they took as a start-up come to the forefront and despite consistent revenue growth, that broker will experience numerous losses and headaches. The broker feels as if everything is out of control; the processes in place no longer work. Sales reps can no longer (nor should they) manage issues arising during transit. The electronic vetting resource for third-party carriers is too simple for business needs. Cargo claims sit, and customers are angry. Unpaid freight charge balances increase. The broker realizes it has outgrown leadership and must make tough decisions. GLG is equipped to address these common broker growing pains. GLG has extensive experience helping brokers with these growing pains, and will help brokers anticipate future phases as well.