About Calleigh
Caleigh Olson built her legal foundation in Ohio and carried it west to Colorado. She earned a Bachelor of Arts and a Bachelor of Science in Political Science and Business Administration from Saint Joseph's College in 2011. She then went on to the University of Akron School of Law, where she received her J.D. in 2018 and served as editor in chief of the Akron Law Review in 2017.
Early in law school Olson combined courtroom exposure and health care systems work. In 2016 she was a legal intern in the Innovations Department at the Cleveland Clinic. That same year she worked as a law clerk for Skidmore and Associates, gaining practical experience in client matters and legal drafting. Those positions ran alongside her law review responsibilities and helped shape her approach to legal research and writing.
After graduation Olson joined the 18th Judicial District of Colorado as a judicial law clerk in 2018. The clerkship added a year of close work on court procedure, motion practice and opinion drafting. It also gave her firsthand experience with how judges assess evidentiary and procedural issues, which has informed the practical advice she offers clients.
Olson moved into private practice in 2020, joining the Business Law Group as a lawyer. Her time there involved counseling business clients and handling transactional matters. In 2022 she took a role as an associate lawyer at Pless Law Office, where she continued to work on commercial matters and support litigation teams. Her career path shows steady movement from academic law work to roles that combine transactional counsel and courtroom preparation.
Peers and supervisors have noted her command of legal writing and procedure, which traces back to her leadership on the Akron Law Review and her clerkship. She is licensed to practice in Colorado and maintains ties to professional circles in the state. Her background in both business administration and political science gives her a practical lens for client issues that involve commercial structures and regulatory questions.
Olson's practice draws on experience in transactional law, court procedure and legal research. She remains based in Colorado and offers services that reflect her earlier roles in judicial chambers, health care innovation, and business law practice. She now practices in Colorado, drawing on experience in business law and judicial clerkship work to advise clients.
