Cassandra Gaines

Cassandra Gaines has a diverse work experience spanning multiple industries and roles. Cassandra started their career at Altria in 2004 as part of Philip Morris USA before moving to Eli Lilly & Co. in 2007. In 2012, they transitioned into the legal field, joining Lewis Brisbois as a Nationwide Transportation Lawyer and Litigator. During this time, Cassandra represented various transportation entities and provided legal advice on freight loss, cargo damage, as well as regulatory issues.

In 2014, Cassandra joined Echo Global Logistics as a Corporate Attorney and Director of Cargo Security, where they offered legal counsel to senior management on transportation regulations, employment matters, litigation, and contract disputes. Cassandra also handled cargo claims and worked with external counsel to manage contractual risks.

Cassandra then joined Schneider National in 2016 as the Associate General Counsel, Claims and Litigation. In this role, they oversaw the legal outcomes of claims and lawsuits arising from trucking accidents, including bodily injury, property damage, cargo loss, and contract disputes.

In 2018, Cassandra founded their own firm, Gaines Law Group, where they worked as a Transportation Lawyer and Risk Consultant. Cassandra provided support to transportation companies and shippers, offering guidance on contracts and industry risks.

In 2021, Cassandra expanded their reach by hosting the MadGaines Live Show, initially as a podcast and later transitioning to FreightWaves. The show aimed to educate and unite shippers, brokers, and carriers within the transportation industry.

Continuing their entrepreneurial pursuits, Cassandra founded Carrier Assure in 2022, where they currently serve as the Founder and CEO. The software developed by Carrier Assure allows shippers and brokers to easily identify top-performing carriers and avoid less reliable ones, streamlining the matching process and minimizing the risk of cargo theft and double brokering.

Throughout their career, Cassandra Gaines has demonstrated their expertise in transportation risk management, legal knowledge, and entrepreneurial spirit, earning recognition as one of the 100 People Transforming Business in North America by Business Insider.

Cassandra Gaines completed their primary education at Erskine Academy, a private high school, from 1998 to 2001. Cassandra then pursued their undergraduate studies at Cornell University from 2001 to 2005, receiving a Bachelor of Science degree in the Charles H. Dyson School of Applied Economics and Finance. After a break, they continued their education at the University of California, College of the Law, San Francisco (formerly UC Hastings) from 2009 to 2012, where they obtained a Juris Doctor (JD) degree in Law.