Family legacy planning services

Jennifer Bailey

Jennifer “Jen” Bailey is a Family Legacy Client Manager, at the Vanguard Group with 24 years of Vanguard experience. Jen has spent 15 years of her career at Vanguard in a learning and development role working as a facilitator, learning consultant and leader of a design team. Jen facilitated for Vanguard’s University for over 10 years.  During that time, she was an expert certified facilitator in Crucial Conversations, Generations in the Workplace, Coaching and Communications courses among many other topics.

Jen has a degree in education with a concentration in psychology from West Chester University. She has had roles at Vanguard and outside of Vanguard counseling families and employees. In her time outside of work, Jen serves as a facilitator for the Association for Talent Development helping professionals obtain adult learning, instructional design, and facilitation certifications.

Jess Rickert

Jess Rickert is a family legacy specialist in Vanguard Personal Advisor Wealth Management™ where she specializes in bridging the communication gap between generations of family members. Jess joined Vanguard in 2013 and previously served as a relationship manager, ensuring her clients' goals were reflected in all areas of wealth planning. Prior to Vanguard, she studied music therapy and worked in market research. She earned a B.S. in international business from the University of North Carolina at Greensboro. She also holds the FINRA Series 7 and 66 securities licenses.

Emily Roesler

Emily specializes in financial education curriculum development, the psychology of money, and the intersection of wealth and interpersonal relationships. She and her team focus on preparing families for successful, multigenerational wealth transfer and financial empowerment. 

Before joining Vanguard in 2021, Emily spent more than 7 years in the ultra-high-net-worth field in a variety of relationship management, education, and meeting facilitation roles.

Emily earned a bachelor’s degree in psychology from Calvin University. She holds a master’s degree in clinical counseling with a trauma concentration from The Chicago School of Professional Psychology.

Kara Washousky-Smith

Kara is a Family Legacy Specialist within Vanguard Wealth Management, where she specializes in bridging the communication gap and financial education between generations of family members. She earned her bachelor's degree in clinical psychology and a master's degree in childhood education from Canisius College in Buffalo. She joined Vanguard in 2016 and served as an Ultra-High Net-Worth Relationship Manager, ensuring clients were meeting their goals across the Wealth Management spectrum. Prior to Vanguard, she worked for the Charlotte Mecklenburg school system as a middle school teacher. She holds the FINRA 7 and 66 securities licenses and is also a Certified Wealth Management Specialist.