Meet our Team

Meet our Team

Our mission at Cummings Wealth Management Group is to deliver a Four Season's experience with FedEx efficiency.

Years of Experience

$325M AUM as of 6/30/23


Group photo


Bobby Cummings, CFP® , AIF®*, CPFA, CFBS


Bobby Cummings is the president of Cummings Wealth Management Group. He earned the CERTIFIED FINANCIAL PLANNER™ certification, is an Accredited Investment Fiduciary® Designee as well as Certified Plan Fiduciary Advisor. 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 40" 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 as well 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.

Forbes Best in State 2022



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2022 Forbes Best In State Wealth Advisors, created by SHOOK Research. Presented in April 2022 based on data gathered from June 2020 to June 2021.  19,640 Advisors were considered, approximately 6,500 Advisors were recognized. Advisors pay a fee to hold out marketing materials. Not indicative of advisor’s future performance. Your experience may vary. Click here for more award information.

2003 Top 40 under 40, created by Charleston Regional Business Journal. This award is based solely on the opinions of the editors and is based on 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 reflect the performance of the advisor. Click here more information. 



Mary Chapman, CFP®

Chief Operating Officer & Director of Financial Planning Services

Mary came to our team in 2012 with a diverse background and strong interpersonal skills. She has 25 years experience working with both non-profit organizations and global teams including GE, and BMW.  You will most likely be interacting with Mary as you work with her and Bobby to build and update your financial plan. She is a CERTIFIED FINANCIAL PLANNER™ Practitioner and teaches Financial Planning at 2 local universities. In addition, she has earned her Master of Science degree in Counseling and her Bachelor of Science degree in Financial Management. Mary also holds her FINRA Series 7 and 66 securities registrations (held through Commonwealth Financial Network®). Whether she's managing the day to day operations of our firm, working on your financial plan, or teaching financial planning to students, she loves helping people make sense out of complexity and chart a path forward. She's passionate about transforming the complex layers of our lives into simple and accessible steps towards our future. 

When not working on finances, you can find Mary, who is a cancer survivor, giving back, mentoring or coaching others.  She specializes in crisis counseling and adult education. Passionate about lifelong learning, she is always learning something new. She has completed her 200 RYT yoga teacher certification, is a certified nutritional counselor, is TEFL certified, and is a triathlete. She is currently working on obtaining her PhD.

Dallas Brewer, CFP®, ChFC®, RICP®, ChSNC®

Director of Retirement Services & Associate Wealth Advior

Dallas joined our team in 2023 and has been in the financial services industry since 2006, with a concentration in individual wealth and retirement plan management.  You will most likely be interacting with Dallas as he helps you with your retirement account and financial planning.


Dallas earned his bachelor’s degree in accounting from Clemson University.  He currently maintains the FINRA Series 6, 7, 63 & 65 securities registrations (held through Commonwealth Financial Network®), and applicable life, accident & health insurance licenses.  He is a CERTIFIED FINANCIAL PLANNER™ professional and holds the Chartered Financial Consultant® (ChFC®), Retirement Income Certified Professional® (RICP®), and Chartered Special Needs Consultant® (ChSNC®) designations from the American College of Financial Services.


Dallas is also an accomplished local musician.  On the weekends you may see him playing music at various venues and events throughout the Lowcountry.  He lives in Charleston with his wife Alicia, son (Dallas), daughter (Page), and family dog Sam.  They enjoy spending time with family and friends at the beach or at a concert.

Terri Cantrell, CRPC®

Director of New Accounts & Service

Terri is our Director of New Accounts & Service and joined our team in 2022. Terri has over 20 years of experience in the financial services industry and holds her FINRA 7 and 66 securities registrations ((held through Commonwealth Financial Network®)  as well as her Chartered Retirement Planning Counselor (CRPC) ®. She loves interacting with clients and supporting you through many service endeavors, ensuring an efficient and smooth experience for all clients. You will most likely be interacting with Terri as she opens and services your accounts.


When away from the office, Terri loves spending time with her six grandchildren and attending yoga/dance classes.


Andrea Zenisek

Director of Asset Movement & Client Services

Andrea is our Director of Client Services and joined our team in early 2023.  She has over 14 years’ experience in the financial services industry and has worked in both the brokerage and institutional areas of finance.  Andrea holds her Series 6, 63 and SIE securities registrations. 

Andrea strives for excellence in serving our clients and is passionate about providing the highest level of support to each of the individuals and families that we work with.  She assists our clients with account related service requests as well as day to day operational and administrative matters.


Originally from Milwaukee, Wisconsin, Andrea moved to Charleston in late 2015.  She was drawn to the city’s beauty, warm weather and beaches.  When not in the office, you will find her spending time outdoors and at the beach with her two daughters.  Andrea also enjoys traveling, running, being active in fitness and participating in Functional Fitness and Spartan racing events.

Jo Lavender

Client Service Concierge

Jo is our Client Service Concierge and joined our team in 2017. Bobby met Jo about 20 years ago and was very impressed. He told her when her boss at the time retired, to please call him! Well, she did, and he hired her over the phone. Jo has more than 30 years’ experience serving clients in our industry.

As defined by the Strategic Coach Unique Ability® 2.0 discovery, her Unique Ability® is in making connections with people and advocating for them on their behalf. You will most likely be interacting with Jo to help you with all your insurance needs. 

Tanya Kenna

Calendar Ninja

Tanya is our Calendar Ninja and joined our team in 2016.  She earned her Bachelor of Science degree in Marketing & Communication from the Universtiy of Rhode Island and has worked in client services for over 10 years. In addition to being a busy mom of 2, she works quietly behind the scenes to keep our office smoothly and efficiently.  You will most likely be interacting with her as she reaching out to schedule our meetings. 

Brian Cummings, CFP®, EA, ChFC®, AEP®

Financial Advisor

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Brian Cummings, a Charleston native, has been in banking and financial services for over 20 years.  He has extensive experience in consumer, commercial, and private banking.  His most recent experiences prior to joining Cummings Wealth Management Group in 2019 were serving in financial advisor and private banking roles for regional and community banks.  His educational background includes a bachelor’s degree from the College of Charleston, as well as, attaining the CERTIFIED FINANCIAL PLANNER™ practitioner, Chartered Financial Consultant™ and Accredited Estate Planner™ professional designations through course work at the College of Charleston and the American College for Financial Services.  Brian also holds a post-baccalaureate certificate in Taxation from the University of North Carolina at Greensborough, as well as, the Enrolled Agent (EA) designation, the highest credential awarded by the IRS.  When not working, Brian enjoys spending time with his wife Mary, their family, and friends.