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® Designee. 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 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.

*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

FullSizeRender Family with marlin flag 05 31 2014 bobby-and-banks Bobby-helping-Habitat Banks-Sky-high-in-the-Keys-2014

Brian Cummings


Brian Cummings, a native Charlestonian, has been in banking and financial services over 18 years.  He has experience as a consumer lender, commercial banker, mortgage banker, as well as both a financial adviser and private banker in wealth management departments for national, regional and community banks.  His educational background includes attaining the CERTIFIED FINANCIAL PLANNER™ certificaton,  as well as Chartered Financial Consultant® and Accredited Estate Planner® professional designations through course work at the College of Charleston, as well as the American College for Financial Services.  When not working, Brian enjoys spending time with his wife Mary, their family and friends.  Generally, you can find them anywhere outdoors enjoying the beach (especially surfing for Brian), on bikes, at the pool, in their garden or out at the barn with their horse Big Horn Ranger, a horse they recently adopted from a not so great career in racing.

Mary Chapman, CFP®

CERTIFIED FINANCIAL PLANNER TM Practitioner and Practice Manager

Mary comes to our team with a diverse background, strong interpersonal skills, and 15 years experience, focusing on analytical finance and team management. She is a CERTIFIED FINANCIAL PLANNER™ Practicioner and our Practice Manager. 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®). 

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 6 years she completed her yoga teacher certification, became a certified nutritional counselor, completed the Mt Pleasant police citizens academy, and most recently earned the CERTIFIED FINANCIAL PLANNERTM certification. Her next goal is to complete an Ironman.

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.

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.


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.

Tanya Kenna

Tanya earned her bachelor's degree in Marketing & Communication from the University of Rhode Island and came to our team with over 5 years experience focusing on client services at a large wealth management firm in Boston. She joined our team in 2015 as our Director of Client Services and did an outstanding job. She took a sabbatical for the birth of their daughter, Natalie, and has joined our team once again to focus on scheduling, marketing, and client service support. You will not find a more willing ear to listen without judgement than you will in Tanya. She is always ready to help and loves interacting with people.

In her spare time, what's left after being the busy mom of a two-year old, Tanya and her husband enjoy playing tennis, traveling, and taking their Bernese mountain dog to the beach.

Connor Kannapell

Connor is our resident intern this fall. He was born and raised in Chevy Chase, MD and is currently a senior at the College of Charleston studying Finance and Economics. Connor is interested in emerging markets and commodities trading. At the College of Charleston, Connor is a member of the Student Finance Club and is active in and around the School of Business. Upon graduation, Connor hopes to pursue a career in investment analysis and portfolio management, utilizing skills learned from interning with both large and small scale wealth management firms. Connor enjoys playing golf and spending time with his friends and family in his free time. He is a lifelong baseball fan and supporter of the Washington Redskins.