Meet Our Team

Meet Our Team

Bobby Cummings*

CFP® , AIF®, Certified Family Business Specialist

Bobby Cummings is the president of Cummings Wealth Management Group. He earned the CERTIFIED FINANCIAL PLANNER certification and is an Accredited Investment Fiduciary®. He has been in business since 1990. His focus is providing wealth advisory services to business owners and professionals. Bobby says, "We are committed to helping our clients make smart decisions about their wealth so that it can help them—and their loved ones—lead fulfilling lives." He created "The Beacon Experience™," which is a process that strives to positively impact our clients by tailoring the financial planning process to the individual needs of his clients.

In 2003, Bobby was recognized by the Charleston Regional Business Journal as one of the "Top 40 under 401" community business leaders. He is passionate about community service and specifically helping children. His personal fund-raisers have brought in more than $50,000 for various children's charities, such as Christmas Commandos, over the years. He has previously served as a board member for Communities in Schools, the Carolina Youth Development Center, and a past president of the Island Club on Sullivan's Island. He currently serves as treasurer for Friends of Sullivan's Island Elementary School, as a Merit Badge Counselor for Boy Scouts Troop 20, and as a Tribe Chief for Y-Princess.

On the weekends you might see Bobby out on the water with his family and friends surfing, fishing, or kayaking. He might also be found out hunting with his Boykin Spaniel, Teal. He lives on Sullivans Island with his wife, Kristin, and their children: Tanner, Keenan, and Banks. Bobby considers them to be his greatest accomplishment.

*Robert J. Cummings is a Registered Representative and Investment Adviser Representative with/offers securities and advisory services through Commonwealth Financial Network®, Member FINRA/SIPC, a Registered Investment Adviser.

1This list recognizes local, young professionals and is based solely on the opinions of the editors of the Charlston Regional Business Journal. They considered the candidates contributions to their company, impact to the business world, and their community service. This award is not specific to financial services and does not imply an endorsement, recommendation, or otherwise reflect the performance of the advisor or any accounts

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Mary Chapman

Practice Manager

Mary was born in the historic town of Saratoga Springs, New York. She earned an associate's degree in marketing, a bachelor's degree in financial management, and a master's degree in counseling. Mary has also earned her FINRA Series 7 and 66 securities registrations (held through Commonwealth Financial Network®). She spent 15 years in the nonprofit and financial services industries working in a variety of roles, focusing on management, finance, and marketing, before joining our team as our financial paraplanner and seasoned practice manager. She brings her passion of helping people, analytical skills, and diverse background to her role with us. She loves helping people with this very personal and very important part of their lives.

When not working on finances, you can find Mary delving into some aspect of wellness or actively volunteering in our community, specializing in the arts, crisis counseling, or adult education. A recent cancer survivor, she is fascinated by life at the cellular level. Passionate about lifelong learning, she is always working on something. In the last 5 years she completed her yoga teacher certification, became a certified nutritional counselor, completed the Mt Pleasant police citizens academy, and is currently working to become a Certified Natural Health Practicioner.

Jo Lavender

Client Service Associate

Jo has been in the financial industry for more than 30 years. Her love of working with people and expertise in client service make her a valuable addition to our team.

Jo has also worked in the fitness industry for more than 35 years as a personal trainer and instructor. When not in the office or helping others achieve their fitness goals, she enjoys running, kayaking, and reading. She and her husband of 33 years have two children and two granddaughters, Anna and Lily, who bring her the greatest joy. “They keep me young and remind me of what is really important in life and that is family,” says Jo.

Josh Coward

Director of Client Services

Josh moved to Charleston from Dillon, SC where he earned his bachelor’s degree in Economics from the College of Charleston.  Josh joins our team with years of experience in financial services and servicing client accounts. His passion for investments as well attention to detail make him a great fit as our Director of Client Services. He currently holds FINRA Series 7 & 66 securities registrations (held through Commonwealth Financial Network®).  In his spare time, Josh enjoys playing golf or being outdoors.


Jackie Reiner

Jackie Reiner is our resident intern for this semester. She will be assisting our team in a variety of tasks related to client services and will be the friendly voice answering your phone calls.


Jackie was born and raised in Hong Kong before moving right outside of Philadelphia to finish up high school. She is currently a senior at the College of Charleston studying Spanish and Business Administration, concentrating in Finance. As a member of the Delta Gamma sorority, she has held numerous positions in Greek Life throughout her years at college, including holding a position on the campus Panhellenic Council as Vice President of Recruitment. During this past summer in Charleston, Jackie worked as a Recreation Coordinator at the Kiawah Island Golf Resort where she worked closely with clients organizing their recreation activities throughout their stay at the resort. Some of Jackie’s biggest passions are traveling, photography, baking, and dancing.

Ingram Baker

Ingram Baker will be our resident intern for this semester. She will be helping with a variety of tasks related to client services and will be the friendly voice answering your phone calls.


Ingram is originally from Murrells Inlet, South Carolina and currently attends The College of Charleston. As a senior at The College, she is pursuing a major in Business Administration.  Outside of the classroom Ingram is a volunteer with Reading Partners at Mary Ford Elementary and teaches kindergarteners basic reading and writing skills. Some of her passions include cooking, traveling, reading and playing tennis.