Lexington, KY W Main St Office

Maisy Lyne is a financial advisor at Robert Baird & Co. based in Lexington, KY, holding a Series 66 designation. She joined Robert Baird & Co. in 2024 and has prior work experience in education and various service roles. Robert Baird & Co.’s DDK Group, part of the Private Wealth Management department, serves individuals, corporate clients, pensions, profit-sharing plans, and charitable organizations through a variety of financial planning, portfolio management, and brokerage services. The firm employs a combination of manager-traded and model-traded strategies, tax-management techniques, and ongoing manager selection supported by internal research and tools.

Jennifer Wooldridge is a financial advisor at Robert Baird & Co. with 20 years of industry experience. She holds a Series 66 designation and has worked at Robert Baird & Co. since 2019 and at JJB Hilliard W.L. Lyons LLC since 2009. Outside of her advisory role, she performs bookkeeping for a family business called Foreign Affairs Autowerks. Jennifer is part of The DDK Group within Robert W. Baird & Co.’s Private Wealth Management department, which serves individual, corporate, pension, and charitable clients through a variety of financial planning and portfolio management services. The firm offers a range of SMA strategies, tax management, and advisory services supported by internal research and partnerships with external managers.

Roseanna Black is a financial advisor at Robert Baird & Co. with a Series 66 designation. She has been with Baird Private Wealth Management since 2021. Prior to her current role, she worked in healthcare and childcare sectors. She is part of The DDK Group within Baird’s Private Wealth Management practice, which serves individuals, families, pensions, corporations, and charitable organizations by providing customized financial planning and portfolio management services.

James Jolly III is a financial advisor at Robert W. Baird & Co. in Lexington, KY, holding a Series 66 designation with three years of industry experience. He has been with Baird since 2022 and previously worked at White Lodging Services and Article Menswear. The DDK Group, a team within Robert W. Baird’s Private Wealth Management department, serves individuals, corporate clients, pensions, profit-sharing plans, and charitable organizations. The firm offers a broad range of services including financial planning, portfolio management, and customized separately managed account programs, combining manager-traded and model-traded strategies alongside ongoing investment research and monitoring.

Mary Osborne is a financial advisor at Robert Baird & Co. with two years of industry experience. She holds the Series 66 designation and previously worked in education, including roles at Junior Achievement of the Bluegrass and several public school districts. She is part of The DDK Group within Robert W. Baird & Co.’s Private Wealth Management department, which serves individuals, corporate and business clients, pensions, profit-sharing plans, and charitable organizations. The firm offers financial planning, portfolio management, and custody services with a focus on manager selection, tax management, and the use of internal research tools.

Jennifer Reisenbichler is a financial advisor at Robert Baird & Co. with 17 years of industry experience. She holds a Series 66 designation and has worked at Robert Baird & Co. since 2019, following nearly 11 years at J.J.B. Hilliard W.L. Lyons. Outside of advising, she is involved in several non-investment ventures including co-owning a maple syrup production business, training and selling horses, and serving on an equine grand jury. The DDK Group at Robert Baird & Co., where she practices, serves a diverse client base including high net worth individuals, business clients, and charitable organizations. The firm offers comprehensive wealth management services with a focus on discretionary and non-discretionary portfolio management, utilizing a range of separately managed accounts, overlay management, and tax strategies.

Richard Hart is a financial advisor with Robert Baird & Co. in Lexington, KY, holding Series 63 and Series 65 licenses and bringing 42 years of industry experience. He previously spent 36 years at J.J.B. Hilliard, W.L. Lyons, Inc. Hart serves as Treasurer for Broadway Baptist Church, providing bi-monthly financial reports. He is part of The DDK Group within Robert W. Baird & Co.’s Private Wealth Management department, which serves individuals, business clients, pensions, and charitable organizations. The firm offers a range of financial planning and portfolio management services, utilizing both manager-traded and model-traded strategies along with tax-management and direct-indexing capabilities.

Theodore Bates Jr. is a financial advisor with Robert Baird & Co. based in Lexington, KY, holding Series 63 and Series 65 credentials and bringing 40 years of industry experience. He previously worked at Hilliard Lyons and J.J.B. Hilliard, W.L. Lyons, Inc. He is involved in thoroughbred horse breeding and serves as an executor and trustee for family trusts. Robert Baird & Co.’s DDK Group operates within the firm’s Private Wealth Management department, serving individuals, business clients, pensions, and charitable organizations with a range of financial planning and portfolio management services. The firm utilizes manager-traded and model-traded SMA strategies, overlay management, and tax-management techniques, supported by internal research and technologies, including artificial intelligence, to deliver advisory services.

Catherine Dimarco is a financial advisor at Robert Baird & Co. with 14 years of industry experience. She holds a Series 66 designation and previously worked at J.J.B. Hilliard, W.L. Lyons, LLC for 20 years before joining Robert Baird in 2019. Outside of her advisory role, she is involved in skincare sales as a Mary Kay beauty consultant. Robert Baird & Co. serves individuals, corporate clients, pension and profit-sharing plans, and charitable organizations through its Private Wealth Management department. The firm offers a range of services including financial planning, portfolio management, and municipal advisory services, supported by internal research and investment professionals.

Stephen Grossman is a financial advisor with Robert W. Baird & Co. in Lexington, KY, holding Series 63 and Series 65 credentials and over 43 years of industry experience. Prior to joining Baird in 2019, he spent more than three decades at J.J.B. Hilliard, W.L. Lyons, Inc. Grossman serves on several boards, including the University of Kentucky Gaines Center for the Humanities and the American Heart Association, where he is chairman. He is part of the DDK Group, a team within Baird’s Private Wealth Management practice that advises individuals, families, pensions, corporations, and charitable organizations. The group offers customized financial planning and portfolio management services, utilizing a range of investment strategies and overlays to meet diverse client goals.

S. Thomas Ogden is a financial advisor at Robert Baird & Co. with 32 years of industry experience. He holds Series 63 and Series 65 licenses and has worked previously at J.J.B. Hilliard, W.L. Lyons, LLC and Citigroup Global Markets. Outside of his advisory role, he is the owner of JC Resorts LLC. Robert Baird & Co. serves individuals, corporate and business clients, pensions, profit-sharing plans, and charitable organizations through a range of financial planning and portfolio management services. The firm employs a mix of manager-traded and model-traded strategies, tax management, and internal research tools, and reported approximately $394 billion in regulatory assets under management as of December 31, 2025.

James Master is a financial advisor at Robert Baird & Co. in Lexington, KY, with 34 years of industry experience. He holds a Series 63 designation and has worked at Robert Baird & Co. since 2019, following a 27-year tenure at J.J.B. Hilliard, W.L. Lyons, Inc. Outside of his advisory role, he serves as treasurer for a local homeowners association. Robert Baird & Co.’s Private Wealth Management department, including the DDK Group where Master works, serves individuals, corporate and business clients, pension and profit-sharing plans, and charitable organizations. The firm offers a range of financial planning and portfolio management services, utilizing manager-traded and model-traded strategies, tax management, and internal research, including artificial intelligence, to support client investment decisions.

William Arnett is a financial advisor at Robert Baird & Co. in Lexington, KY, holding a Series 66 designation. He has been with Baird since 2024, with prior experience including a role at Worthington Hills Country Club and periods as a student. He is part of The DDK Group, a team within Robert W. Baird & Co.’s Private Wealth Management practice that advises a range of clients including individuals, families, pensions, and institutional clients. The group offers customized financial planning and portfolio management services, utilizing both in-house and third-party managers across traditional and non-traditional investment strategies.

Thomas Kessinger is a financial advisor with Robert Baird & Co. in Lexington, KY, holding Series 63 and Series 65 licenses and bringing 33 years of industry experience. He previously worked at J.J.B. Hilliard, W.L. Lyons, Inc. from 1993 to 2019. Outside of his advisory role, he serves as co-trustee of family trusts and is an investor in a restaurant chain with no active responsibilities. He is part of the DDK Group within Robert W. Baird & Co.’s Private Wealth Management department, which serves individuals, corporate and business clients, pensions, profit-sharing plans, and charitable organizations through comprehensive financial planning, portfolio management, and brokerage services. The firm uses a combination of manager-traded and model-traded strategies, internal research tools, and strategic partnerships to deliver investment advice.

Margaret Sutton is a Series 66-licensed financial advisor with 12 years of industry experience. She has worked at Robert Baird & Co. since 2019 and previously spent six years with J.J.B. Hilliard, W.L. Lyons, LLC. She is based in Lexington, KY. Margaret is part of The DDK Group, a team within Robert W. Baird & Co.’s Private Wealth Management department that serves individuals, corporate clients, pensions, profit-sharing plans, and charitable organizations. The firm offers a variety of services including financial planning, portfolio management, and custody, utilizing a blend of manager-traded and model-traded strategies supported by internal research and technology.