Bailey joined the firm in October of 2023 as an associate attorney. Before she began at Childress Ahlheim Cary LLC, she clerked for the Honorable Paul C. Wilson at the Supreme Court of Missouri immediately after her law school graduation from 2019–2021. She then went on to work for the Missouri State Board of Registration of the Healing Arts, where she was promoted to General Counsel. After her time with the Board, she worked at a defense firm in Columbia, Missouri, where her practice focused mostly on personal and commercial automobile accidents, wrongful death, premises liability, breach of contract, first party insurance matters, and bad faith litigation. Bailey has a wide breadth of experience in all stages of litigation, including pre-lawsuit negotiations, written discovery, depositions, and drafting applications for transfer and writ.

When Bailey is not busy at work, she enjoys spending time with her husband and their three dogs, painting, golfing, cheering on the Mizzou Tigers, and generally spending time outdoors. She also volunteers as much time as she can to engage with law school students at her alma mater, the University of Missouri School of Law.