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
Personal Financial Advisor
Jay Cutrera began his career in financial services at TCF Bank in 2002, where his personable style, commitment to follow-through, and ability to connect with clients led him into work as a registered representative helping bank customers with their investments.
After several years, Jay recognized that his clients’ needs were becoming more sophisticated than what a bank-based platform could fully support. He moved to Charter One Bank as an Investment Advisor Representative, where he continued expanding his experience with clients while developing a clearer vision for the kind of client-focused practice he wanted to build.
In 2010, Jay established Cutrera Financial so he could build a private practice centered around client relationships, practical guidance, and long-term financial decision-making. Since then, he has worked with individuals, families, and business owners throughout Chicago and the surrounding suburbs, helping them organize their financial picture, prepare for retirement, review investment strategies, and navigate the changes that life and markets inevitably bring.
Outside the office, Jay enjoys playing and watching sports, and he has coached his young nephew’s football team. He and his wife, Kasia, live in the northern Chicago suburbs.
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.