James A. “Jimmy” Jacobs CLU® , ChFC®


James A. “Jimmy” Jacobs, CLU, ChFC began his financial services career with Equitable Life Assurance Society of U.S. (now Equitable), January 1971.  January 2024, he celebrated 53 years in the financial services business.


After 47 years with AXA Equitable, he retired in September 2018, affiliated with The Pinnacle Group, a National Life Brokerage Firm, and joined an independent broker dealer, the Leaders Group, for security trades and the sale of variable life insurance and annuities products.  He transferred over 2,000 policy holders.


When he left Equitable, Jimmy ranked among the top 25 in lifetime production among all Equitable associates in the history of the company. In 2003, he was named the National Honor Agent, THE HIGHEST AWARD IN THE COMPANY.  This award is given annually by the Equitable Old Guard (Agency Managers) based on career production, industry and community service.  He is a charter member of EARC – Equitable Agents’ Reinsurance Company and continues as a member. 


Since joining The Leaders Group, Jimmy has finished among the top four retail producers nationally in total production and the top producer in Variable Annuity sales annually.


He earned his Chartered Life Underwriter (CLU) designation in 1976 and Chartered Financial Consultant (ChFC) designation in 1982.  He completed an elite Wealth Retirement Planning Program with Wharton School in January 2006.  Jimmy served as a District Manager with The Equitable from 1982 to 1990, winning several management awards.  He retired from management in June 1990 to open his own office, Jacobs Financial Group, Inc. in Chesterfield, Virginia.  In 2018, he changed the company name to Milestone Financial Solutions.  Today the company employs 7 people, including Brandon Smith, MBA, CLU, ChFC, his Junior Partner.


During his career, Jimmy has been extremely active in the industry:  NAIFA member for 53 years, past President State of Virginia in 1981 and a member of the Virginia Life Underwriters Hall of Fame, MDRT 52 years, serving on various boards and committees;  the Society of Financial Service Professionals (FSP) since 1976;  member of AALU (now Finesca) since 1990, Membership Chair in 2009,  and the Life Foundation board from 2007-2011.  Currently, he is also a member of the Forum 400 and Life and Qualifying Member of top of the table division of MDRT.


Jimmy has spoken to numerous Life Underwriters groups throughout the United Sates and Canada, several National Equitable conferences, and has been a speaker at the prestigious Million Dollar Round Table seven times including main platform in 2003.  He was a main platform speaker at the Top of the Table annual meeting in 2006, and a main platform speaker at the MDRT Hour featured during the 2001 annual NAIFA Convention.  Jimmy has been published several times in Life Insurance Selling and Life Association News.  In October 2001, he was featured in Newsweek as one of five national winners in the Real-Life Stories competition sponsored by NAIFA and the Life Foundation.  Again in 2015, he was one of five national winners of the Life Foundation Real Life Stories competition and spoke at the NAIFA, 2015 annual convention.


He has spoken at the Annual Leaders Group Conference for the last 3 years.


Over the years, Jacobs has also been active in the community.  Some highlights include past President of the Petersburg Breakfast Kiwanis Club, past President of the Petersburg YMCA and past Chairman of the Petersburg United Way Board.  He served on the Hospitality House Board in Richmond, Virginia from 2009-2009.

He is also past co-chairman of Corporate Funding for the Appomattox Regional Governor’s School in Petersburg, a school for gifted students in Technology and the Arts which opened in 2002.  In 2003, he served as chairman of the Southside Virginia United Way campaign.  In 2017-2018, he served on the Chesterfield Arts Foundation and Fund-Raising Board.  The $16-million-dollar facility, built in partnership with Chesterfield County, was completed and opened in 2018.


He served as Chairman for four Petersburg High School 60’s Mega Reunions (graduated classes from the 60s-70s), four days of convention style events with an average of 500 or more participants;

2000 and 2007 at the Cavalier Hotel in Virginia Beach, 2015 at Kingsmill Point, Williamsburg, Virginia and 2023 at Wyndham, Virginia Beach, Virginia.


Jimmy and his wife, Isabel, have been married for 48 years, and have two married children and three grandchildren.

Brandon Smith MBA, CLU®, ChFC® MBA, CLU®, ChFC®, LUTCF®

Executive Vice President
804 768 0541

Brandon Smith is a dedicated financial consultant and planner based in Chesterfield, Virginia. Since graduating from The University of Mary Washington with a Master of Business Administration in 2015, he has dedicated his time to cultivating a wealth of knowledge and experience in the financial services industry. His diverse skillset and expertise enable him to offer comprehensive short-term and long-term financial and business planning catered to the needs of each client. 

Brandon decided to begin his career by relocating to the Richmond area where he became part of Jacobs Financial Group, which has since transformed into Milestone Financial Solutions. Since 2016, Brandon has consistently delivered exceptional value and expertise to both clients and our firm, as well as continued his education in the industry.

As an Eagle Scout, he deeply understands the significance of trust and dedication. Brandon is wholeheartedly committed to the success of the individuals and businesses that rely on Milestone for their financial security. When he's not immersed in financial matters, you’ll find Brandon exploring the great outdoors. He enjoys biking, camping, and hiking through Virginia’s beautiful State Parks. His wife, Rachael, and their dog, Luca, often accompany him on these adventures.


LUTCF Designation (2017): Demonstrating commitment to lifelong learning and professional growth.

CLU Designation (2021): Recognizing expertise in insurance and estate planning.

ChFC Designation (2023): Highlighting comprehensive knowledge of financial planning.



Sally J. Baker

Health Insurance Operations
8047680541 x 101

Sally began working with Milestone Financial Solutions in March 2000. She specializes in group medical and dental insurance, group life and disability insurance, individual medical coverage and Medicare Supplement Coverage. Sally has 19 years' experience in the healthcare field and over 40 years of experience in administration and operations. Sally thoroughly enjoys working with our clients and helping them to find the best coverage to fit their needs at an affordable price. 

Eva E. Charity

Client Service Specialist
804 768 0451

Eva has over 40 years of experience within the Financial Services industry; she started with The Equitable while in high school and helped clients with various service issues until she left in 1999 to join Jacobs Financial Group, now Milestone Financial Solutions. Eva's experience and knowledge often make her the first point of contact for clients with questions about their policies and accounts.