Bob Leonardo, Managing Director at MassMutual

Bob Leonardo, Managing Director at MassMutual I provide a total financial needs analysis through a network of experienced professionals. Charles Chamber and Oswego Chamber.

Bob Leonardo is a Financial Services Executive of WWM Investments, LLC in Chicago, a firm with $500 million in assets under advisement. In his role, Bob provides families and business owners with comprehensive financial planning, wealth management solutions and risk management plan design. Bob specializes in working with divorced individuals, helping them transform challenging life transitions int

o opportunities for growth and change. Utilizing an open and transparent process, Bob manages each client’s unique financial needs, providing protection planning and investment advisory services tailored to their objectives. Bob has worked as a financial advisor since 2003, providing personalized service to clients and businesses nationally. Prior to joining WWM, Bob was ¬a Managing Director of Hoopis Group, where he was recognized as a top advisor for twelve consecutive years. Each year since 2010, Bob has been a member of the Million Dollar Round Table, which recognizes top financial services industry producers and leaders. Bob is committed to giving back to his community serving as a member of the Naperville Area Chamber of Commerce, St. Bob received his bachelor’s degree in Economics from Villanova University. He is a Registered Representative and member of the National Association of Insurance and Financial Advisors. Bob resides in Naperville with his wife Colleen, his two sons and daughter.

Life insurance doesn’t have to be complicated or expensive. It just has to be right for your life. Whether you’re starti...
09/08/2026

Life insurance doesn’t have to be complicated or expensive. It just has to be right for your life. Whether you’re starting out or approaching retirement, I can help you find
coverage that fits. Contact me today.

AM Best, S&P, and Moody’s ratings are key elements when determining the strength of an insurer. Let’s talk about who the...
08/27/2026

AM Best, S&P, and Moody’s ratings are key elements when determining the strength of an insurer. Let’s talk about who these organizations are and what their ratings mean for
your retirement planning.

When a business is part of the picture, trust planning can help balance family needs with long‑term continuity goals. Co...
08/24/2026

When a business is part of the picture, trust planning can help balance family needs with long‑term continuity goals. Coordinating with legal and tax advisors can help create a structure that supports both.

Let’s connect and discuss first steps.

Variable annuities can be a great option for those looking to bolster their retirement income needs but don’t want to gi...
08/21/2026

Variable annuities can be a great option for those looking to bolster their retirement income needs but don’t want to give up on the potential for growth. Does your retirement plan align with your future retirement income needs?

Estate planning isn’t only about transferring wealth, it’s about transferring intentions.Many families are starting conv...
08/17/2026

Estate planning isn’t only about transferring wealth, it’s about transferring intentions.
Many families are starting conversations earlier, thinking about how their values, priorities, and goals carry forward across generations. In many cases, the process can be just as meaningful as the outcome.

Let’s chat about how I can work alongside you on your estate planning goals.

While Social Security is foundational, additional guaranteed income sources can improve retirement stability — particula...
08/13/2026

While Social Security is foundational, additional guaranteed income sources can improve retirement stability — particularly in volatile markets. Let’s talk about the role
retirement income has in your portfolio.

Business growth, family changes, and new responsibilities can all impact how well an estate plan still fits your busines...
08/10/2026

Business growth, family changes, and new responsibilities can all impact how well an estate plan still fits your business and your life. A periodic review can help ensure your plan reflects where life and business are today — not years ago.

Let’s review your options.

There is a growing concern about outliving savings, inflation, and market swings — driving demand for income strategies ...
07/30/2026

There is a growing concern about outliving savings, inflation, and market swings — driving demand for income strategies that offer stability and protection without sacrificing growth. Let’s talk about retirement strategies that offer the ability to use the market for growth.

Variable annuities have become more competitive and when paired with the market, they could offer growth potential. Let'...
07/24/2026

Variable annuities have become more competitive and when paired with the market, they could offer growth potential. Let's talk about how a variable annuity can support continued growth throughout retirement.

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2441 Warrenville Road Suite 300
Lisle, IL
60532

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