Flat-fee, roth conversion strategy financial advisors in Chicago, IL
The right financial advisor for you depends on how you weigh location, expertise, experience, the clients they typically serve, and how they work with you.
If you’re considering a Roth conversion, it’s often because you expect your tax rate to rise in the future or want to avoid taxes on retirement income. A common mistake is treating the conversion as a simple tax swap without considering how it fits into your long-term financial picture.
- Tax timing insight. Look for advisors who explain how to balance paying taxes now versus later, especially since Illinois doesn’t tax retirement income.
- Property tax impact. Since property taxes can be high in Chicago, ask how they factor this into your overall tax strategy.
- Flat-fee clarity. Confirm how their flat fee covers the complexity of Roth conversions, so you know what services you’re paying for.
- Account sequencing. Good advisors will discuss which accounts to convert first based on your income and tax bracket projections.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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James B
Series 63, Series 65
La Grange Park, IL
Sequent Planning, Llc
James Beran specializes in Roth conversion strategy and retirement income planning, offering flat-fee financial planning services ranging from $500 to $5,000, which suits clients seeking clear cost structures in Chicago's tax environment. His firm, Sequent Planning, LLC, manages nearly $395 million with ETF-based models and serves both individuals and retirement plan sponsors, providing a blend of strategic asset management and retirement consulting.
Experience: 1 year
Avg account: $98,000
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Samuel M
Series 65
Chicago, IL
Stride Investments, LLC
Samuel McElroy specializes in Roth conversion strategy and retirement income planning, making him well-suited for clients in Chicago considering flat-fee Roth conversions. With 13 years of experience and a flat-fee structure for strategic tax planning, he offers independent advice through Stride Investments, which emphasizes purpose-based investing and serves high-net-worth individuals and corporate accounts.
Experience: 13 years
Avg account: $376,175
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Melissa O
VerifiedSeries 66
Northbrook, IL
Strategic Advisors of Illinois
Melissa Osuch specializes in Roth conversion strategy and retirement income planning, offering flat-fee financial planning packages with tiered ongoing fees, which suits clients seeking clear cost structures in the Chicago area. Her 20 years of experience and involvement in tax preparation through AMM Accounting Services provide a comprehensive approach, differentiating her from advisors who may not integrate tax insights with investment management.
Experience: 20 years
Avg account: $550,974
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Timothy P
CFP®, Series 63, Series 65
Chicago, IL
One Wealth Capital Management, LLC
Timothy Pearce specializes in Roth conversion strategy and retirement income planning, making him well-suited for clients in Chicago considering flat-fee Roth conversions. His firm uses a macro-environmental, top-down investment approach and offers flat-fee financial planning ranging from $10,000 to $100,000, catering to high-net-worth individuals including founders and executives with 10 years of industry experience.
Experience: 10 years
Avg account: $1,154,660
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Anthony C
Series 63, Series 66, Series 65
Chicago, IL
WealthSpire Advisors
Anthony Cruz specializes in Roth conversion strategy with 19 years of experience at Wealthspire Advisors in Chicago, offering flat-fee financial planning starting around $5,000 annually. His firm serves high-net-worth clients with a relationship-driven, institutional-style investment approach, differentiating him by combining tax-aware retirement income planning with trust administration and diversified asset allocation.
Experience: 19 years
Avg account: $3,410,246
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