Our Passion Is Helping You Pursue Your Goals

Jeffrey D. Montgomery, CTS™, CES™ is the founder and president of Montgomery Financial, a fully independent Registered Investment Advisory firm. As a financial coach, Jeff is passionate about helping retirees and pre-retirees gain a greater understanding of the importance of building a comprehensive financial strategy for retirement. Through Montgomery Financials Inspiration Process™, he helps clients address four key areas of retirement planning: investments, income, tax planning, and estate planning.

After graduating from Towson University in 1991 with a degree in business and economics, Jeff began his career with T. Rowe Price in Baltimore, Maryland, where he specialized in investment services. Today, he brings more than 34 years of experience to his work with retirees and pre-retirees as they prepare for and navigate some of the most important financial decisions of their lives.

Jeff holds two nationally recognized professional designations: CTS™, Certified Tax Specialist™, and CES™, Certified Estate and Trust Specialist™. The CTS™ designation reflects graduate-level education in personal income taxes, retirement plans, deductions, credits, capital gains, payroll taxes, and tax planning strategies. The CES™ designation, granted by the Institute of Business & Finance, is designed to provide advanced education in estate planning, postmortem planning, and taxation. CES™ designees must complete a comprehensive education program, pass exams and a written case study, meet experience and/or educational criteria, complete ongoing continuing education, and agree to follow the IBF Code of Ethics and Standards of Practice.

Jeff understands that retirement planning often involves more than investment decisions alone. It may also include coordinating income needs, tax considerations, estate planning priorities, family goals, and legacy wishes. His additional estate and trust education helps support client conversations around topics such as wills and trusts, asset titling, beneficiary planning, probate considerations, powers of attorney, healthcare directives, and the transfer of assets between generations. While Montgomery Financial does not provide tax or legal advice, Jeff helps clients understand key planning considerations and encourages coordination with qualified tax and legal professionals when appropriate.

Jeff regularly conducts public seminars and educational events to share his knowledge with the community. His topics often include retirement planning, tax-aware strategies, estate planning considerations, behavioral finance, and helping clients navigate the emotions that can come with investing. Investor coaching is so important to Jeff that he equipped Montgomery Financials corporate offices with a state-of-the-art financial resource center, where he and his team help educate clients about their financial strategies in a high-tech environment.

Jeff works primarily with pre-retirees, retirees, seniors, and affluent small-business owners, helping them develop personalized strategies designed to support their financial goals, protect their assets, and thoughtfully plan for income, taxes, estate considerations, and wealth transfer.

Outside of work, Jeff resides in Berlin, Maryland, with his wife, Joan. They have two grown children. He enjoys the outdoors, golf, and offshore fishing on his boat.