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Meet Our Team

We believe our teamwork approach adds a broader perspective to all we do and provides increased benefits to our clients.

When it comes to investing, our professionals are well-versed in both time-tested principles and cutting-edge strategies. Whether you are a seasoned investor or just starting, we are here to help you navigate the markets with confidence.

David B. Winston

Wealth Advisor

David B. Winston is the Executive Wealth Advisor of Winston Wealth Advisors. For more than 29 years David and his team have helped hundreds of families throughout the United States prepare and enjoy their retirement years.

Jacob Winston

Wealth Strategist

At a young age, Jacob showed a passion for mathematics leading him to pursue a career in finance and investments. He graduated with a B.A. in finance, before completing the Certified Financial Planner® program through Boston College.

Tara Kincaid

Relationship Manager, Financial Planning

Tara uses a holistic approach to help families, small business owners, and young professionals create customized paths to financial freedom. This includes helping clients align their values and decision-making with their retirement dreams.

Ashley Hougland

Relationship Manager, Financial Planning

Ashley integrates new clients, conducts planning sessions, and maintains client relationships. She believes that a strong relationship is essential to effectively care for each aspect of a client’s investment and life planning needs. 

Dianna Hill-Dunlap

Director of Operations

Dianna brings more than 40 years of experience in the financial planning industry to Winston Wealth Advisors. Her background and experience bring valuable depth to the operational activities of Winston Wealth Advisors.

Cassie Herrera

Client Relations Manager

Cassie joined Winston Wealth Advisors in January 2017. She assists both our clients and advisors. Her responsibilities range from managing client communications to facilitating day-to-day company operations.

We create financial strategies tailored to your goals

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