Our Team

Bailey Medeiros is the President and Founder of the Women’s Empowerment Scholarship. After graduating as Salutatorian from Monson High School in 2015, Bailey went on to study Finance, Communication, and Legal Studies at Bryant University. In 2019, she received Bryant University's Excellence in Finance Award when she graduated Summa Cum Laude and 9th in her class. Bailey's time at Bryant included being a member of the Special Olympics Committee and the Vice President and co-founder of Bryant’s Law Society. Additionally, Bailey served as an Executive Board Member for Bryant's Archway Investment Fund. In this role, she represented the less than 10% of females tasked with managing a $1.3 million equity portfolio.

In 2016, while an undergraduate student at Bryant, Bailey began her two-year tenure as a member of the New England Patriots Cheerleaders. While on the squad, she traveled to Super Bowl LI in Houston and Super Bowl LII in Minneapolis. 

In 2022, Bailey received her Juris Doctor from Boston University School of Law. Upon passing the Massachusetts Bar Exam, Bailey started as an Associate at Kirkland & Ellis, the world's largest and most profitable law firm. During her time at Kirkland, Bailey represented private equity clients in multi-million and billion-dollar M&A transactions, financings and investment fund matters.

In 2024, Bailey moved to Florida, passed the Florida bar exam and started her own estate planning firm, Bailey Legacy Law. In this role, Bailey creates tailored estate plans to help her clients safeguard what matters most to them. She is passionate about helping families prepare for their futures and protect their assets through trusts, wills, powers of attorney, and healthcare directives. 

Learn more about Bailey and her motivations by visiting the “My Story” tab.