Top roth conversion strategy financial advisors in Illinois
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 manage taxable income in retirement. A common mistake is treating the conversion as a simple tax event rather than a strategic, multi-year plan.
- Tax bracket timing. Ask how they plan conversions to keep you in lower tax brackets over several years, not just the current one.
- Coordination with tax pros. Confirm how they work with your CPA to handle state taxes and Medicare premium impacts.
- Account prioritization. Find out which accounts they recommend converting first and why, based on your overall withdrawal strategy.
- Flat-fee clarity. If they charge flat fees, understand what services are included to avoid surprises during your conversion journey.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
-
Dillon G
Series 65, Series 63
Chicago, IL
WealthSpire Advisors
Dillon Gorham specializes in Roth conversion strategy and retirement income planning, making him well-suited to help Illinois clients manage tax-efficient retirement transitions. Operating from Wealthspire Advisors, a large firm with a flat-fee structure starting at $5,000 annually, he serves high-net-worth and established professionals, offering a customized, institutional-style investment approach that differentiates him from advisors with smaller client bases or different fee models.
Experience: 4 years
Avg account: $3,410,246
-
James B
Series 63, Series 65
La Grange Park, IL
Sequent Planning, Llc
James Beran specializes in Roth conversion strategy and retirement income planning, making him well-suited to help Illinois clients manage tax bracket timing and account prioritization during conversions. Operating independently with a flat-fee structure, he offers fixed financial planning fees from $500 to $5,000 and manages assets through ETF-based strategic models, providing a clear, cost-effective approach compared to advisors with higher or negotiable AUM fees.
Experience: 1 year
Avg account: $98,000
-
Brian R
CFA®
Highland Park, IL
Checkpoint Financial Planning
Brian Rhoads specializes in Roth conversion strategy with a focus on tax-conscious, multi-year planning to manage taxable income in retirement. Operating from Highland Park, IL, he offers flat-fee, project-based financial planning emphasizing retirement income and business exit strategies, distinguishing himself with a risk-aware approach and written reports after video consultations, without managing assets or charging fees based on assets under management.
Experience: 2 years
Avg account: $0
-
Samuel M
Series 65
Chicago, IL
Stride Investments, LLC
Samuel McElroy specializes in Roth conversion strategy with 13 years of experience, focusing on retirement income and Social Security optimization, which suits those planning tax-efficient retirement transitions in Illinois. His firm, Stride Investments, offers flat-fee strategic tax planning consultations and independent, fee-based investment management, catering to established professionals and business owners seeking coordinated, purpose-driven retirement solutions.
Experience: 13 years
Avg account: $376,175
-
Jason M
Series 65
Bloomington, IL
Three Sixty Wealth Management, LLC
Jason Marion specializes in Roth conversion strategy and general retirement planning, making him well-suited to help Illinois clients manage tax bracket timing and account prioritization during conversions. Operating independently with a negotiable fee structure that includes flat fees and AUM-based charges, he offers personalized service through Three Sixty Wealth Management, a firm managing $154.2 million for 166 clients with a long-term, fundamental investment approach.
Experience: 0 years
Avg account: $1,021,993
Want help finding the right advisor?
Answer a few questions to see advisors matched to you.
Advisors focused on
People also searched
Popular in Illinois
Find advisors by type
Not sure where to start?
We'll help you think it through—whether you ultimately need an advisor or not. Warmer helps you compare advisors clearly, so you can choose with confidence.
For advisor listings, we rely on sources including public filings and data provided by advisors, and we cannot guarantee that all information is current or accurate. Advisors are independent and may not have reviewed or updated this information. Please review an advisor's Form ADV and do your own diligence before deciding whether to work with them.
Advisor matching and referrals are provided by FinanceHQ LLC ("FHQ"), a wholly-owned subsidiary of Warmer and an SEC-registered investment adviser. We may be compensated by participating advisors. You pay no fee to use our matching service, and advisor fees are not increased because of a referral. We do not supervise advisors, manage or hold assets, guarantee performance, or provide advice about specific investments.
By using our service, you agree to the Warmer Terms of Service and FHQ Advisory Agreement, and acknowledge Warmer's Privacy Policy. Please review FHQ's ADV Part 2A and Form CRS. Logos provided by Logo.dev
© 2026 Warmer Holdings Inc. ("Warmer")