Retirement Planning
Talk through income, timing, account structure, and the decisions that come with moving into the next stage.
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Meet the Advisor
Registered Representative
After earning his bachelor's degree from Columbia University, David began his career in financial services with large banking institutions, including TCF and Citibank. Over more than two decades in the banking industry, he worked with clients on investment and financial planning needs, earning recognition and branch management positions along the way.
As his career progressed, David found that the most rewarding part of his work was building long-term relationships and helping clients navigate important financial decisions. He eventually established his own financial practice, allowing him to spend more time understanding each client's unique circumstances and providing a more personalized planning experience than was possible within a traditional banking environment.
Today, David works with individuals and families to help them organize their financial lives, evaluate opportunities and risks, and make thoughtful decisions aligned with their long-term goals. His approach emphasizes clear communication, practical guidance, and helping clients feel more confident about the financial choices in front of them.
Outside of the office, David enjoys spending time with his wife and their chocolate lab. He is an avid baseball fan whose loyalties are split between the Cubs and Yankees, and he also enjoys golfing and skiing whenever he has the opportunity.
Planning Conversations
Whether you are preparing for retirement, reviewing investments, or trying to organize the moving parts of your financial life, the first conversation is meant to bring clarity.
Talk through income, timing, account structure, and the decisions that come with moving into the next stage.
Review whether your current investment approach still fits your goals, time horizon, and comfort with risk.
Bring accounts, policies, statements, and questions into one more organized conversation.

Financial guidance for individuals, families, and business owners throughout Chicago and the surrounding suburbs.
Phone: 1.800.533.6750
Fax: 800.533.6750
6836 West North Ave
Chicago, IL 60707
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Securities and Advisory Services are offered through United Planners Financial Services of America, a Limited Partnership, member FINRA/ SIPC.
Cutrera Financial and United Planners are independent companies, and do not offer legal or tax advice.
Information presented on this site is developed from sources believed to be providing accurate information and is intended for informational purposes only. The content presented does not intend to make an offer or solicitation for the sale or purchase of any product or security, nor should it be construed as investment, legal, or tax advice. Investments involve risk and unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed here. The information being provided is strictly as a courtesy.
This site is designed to provide general educational information only and nothing herein should be construed as investment, legal, or tax advice or an offer to sell any product. Please be advised that presently Jay Cutrera holds series 6, series 63, series 7, and series 65 licenses in CA, FL, IL, IN, MI, MN, NY, TX, and WI. For residents of other states in which registration is not held, proper licenses and registrations must be obtained by representatives before proceeding further. No part of this communication should be construed as an offer to sell any security or provide investment advice or recommendation.