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Serving Clients in Chicago and the Suburbs Since 2002!

Jay and the Cutrera Financial team help clients organize their financial lives, prepare for retirement, and make thoughtful decisions through changing markets, changing rules, and changing priorities.

How We Help

Advice that helps you see the whole field.

The goal is not to add to your plate. It is to help you understand what you have, identify missing pieces, and working together so each part of your financial life can work together.

Retirement Planning

Prepare for the shift from saving to spending with a clearer view of income needs, timing decisions, and long-term priorities.

Start here

Investment Guidance

Review your portfolio, risk exposure, time horizon, and investment approach so your strategy has a reason behind it.

Review your lineup

Insurance & Protection

Evaluate whether your protection strategies still fit your family, income, business, and estate planning needs.

Check coverage

Financial Organization

Bring scattered accounts, statements, policies, and questions into one organized conversation.

Get organized

The Cutrera Financial Approach

Built to adjust when life throws a curveball.

Planning is not a one-time document. It is a working relationship that helps you make decisions with context, direction, and steady communication.

Know the field

We begin by understanding your full picture: family, income, investments, insurance, concerns, and goals.

Build the lineup

We coordinate strategies around the financial questions that matter most to you, rather than treating each account in isolation.

Stay ready

We revisit the plan as markets, tax rules, family needs, and life events change over time.

Becoming a Client

A first conversation should make things clearer.

You do not need to arrive with everything perfectly organized. Bring the questions, concerns, statements, or decisions that have been sitting on your mind. The first step is simply understanding where you are and whether our team is the right fit to help.

Start with a conversation. We learn what prompted you to reach out and what you want help sorting through.
Review the moving parts. We look at the accounts, goals, risks, and questions that need attention.
Clarify next steps. You leave with a better understanding of what working together could look like.
Jay Cutrera

Jay R. Cutrera

Personal Financial Advisor

David Lewitas

David Lewitas

Registered Representative

Request an Appointment

Ready to talk through your financial picture?

Schedule an no-cost introductory conversation with the Cutrera Financial team.

Phone 1.800.533.6750

Fax         800.533.6750

6836 West North Ave

Chicago, IL 60707


Check the background of this advisor on FINRA’s BrokerCheck.