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

Mary comes to our team with a diverse background, strong interpersonal skills, and 15 years experience, focusing on analytical finance and team management. She earned her Master of Science degree in Counseling and her Bachelor of Science degree in Financial Management. Mary also currently holds her FINRA Series 7 and 66 securities registrations (held through Commonwealth Financial Network®). 

She brings her passion of helping people, analytical skills, and diverse background to her role with us. She loves helping people make sense out of complexity and chart a path forward. She's passionate about transforming the complex into simle and accessible steps. 

When not working on finances, you can find Mary, who is a cancer survivor, actively volunteering in our community. She specializes in the arts, crisis counseling, and adult education. 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 FINANCIAL PLANNERTM professional.

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.


Matt Whipple, CFP®, MBA

Director of Participant Services

Matt graduated from Western Michigan University with a B.S in Finance.  He is a CERTIFIED FINANCIAL PLANNER™ professional since 2004 and has been providing financial guidance for more than 17 years.  He is a College of Charleston Alumnus achieving an MBA with a concentration in Finance.  In his free time, Matt enjoys getting involved in the community and playing tennis through the United States Tennis Association.

Breyonna Davis

Breyonna was born in El Paso, Texas but claims Irmo, SC as her home (military brat). She's a senior finance major with a minor in International Studies with a concentration in Africa at the College of Charleston. Her hobbies include attempting to learn how to knit, hanging out with her puppy Bentley and reading. Her involvement at the College includes being the program coordinator for the Alternative Break program, a member of the Schottland Scholars and being the president of the Microfinance club.  After college, she plans on serving with the Peace Corps in Benin as a Sustainable Agricultural Systems Extension Agent pending medical and legal clearance.

Anthony Nguyen

Anthony was born and raised in Charleston, South Carolina. He is currently a senior at the College of Charleston studying Finance. Anthony was involved in research with the Finance Department at the College of Charleston focusing on international markets specifically China and on another project researching the benefits of 529 Plans and how to further improve those investments. He was also the student coordinator for the Finance tutoring program at the College. With nearly 5 years of customer service at Nike under his belt, he hopes to use these skills throughout his career to help foster relationships to create to financial wealth and health. Some of Anthony’s biggest passions are health and well-being, basketball and Nike.

Alex Willer

Alex was born and raised in Greenville, South Carolina. He is currently a senior at the College of Charleston studying Finance with a minor in Economics. Some of Alex’s biggest passions are swimming and golfing.

Claudia Dykstra

Claudia Dykstra was born in Philadelphia, Pennsylvania and moved to Charleston, SC for college in 2015. She is currently a student at the College of Charleston pursuing a Bachelor of Science degree in Marketing and Minoring in Finance. Throughout college, Claudia has participated in the AMA club, the Finance Club, and was the Marketing Director for Chi Omega in 2018. She studied for a semester abroad in London, England during her Junior year of college. After Junior year, Claudia traveled to Ghana, Africa for two weeks in the summer on a service trip with Project. Claudia enjoys travelling and staying active whether it is through yoga classes or taking a walk through beautiful downtown Charleston. After Claudia graduates in May 2019, she hopes to move to New York City and pursue a job in Financial Planning.