Top medicare planning financial advisors in Wisconsin

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.

You need a Medicare planning advisor when you're approaching age 65 or navigating changes in your health coverage options. Without expert guidance, it's easy to miss enrollment deadlines or choose plans that don't fit your health needs and budget.

  • Enrollment timing. Confirm how they help you avoid costly late enrollment penalties by tracking your specific eligibility windows.
  • Plan comparison. Ask how they evaluate Medicare Advantage, Part D, and supplemental plans to match your medications and providers.
  • Coordination with other coverage. Ensure they consider how Medicare works with any employer or retiree insurance you have.
  • Cost management. Discuss strategies they use to minimize out-of-pocket expenses while maintaining necessary coverage.

Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.

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Kayla W

Series 63, Series 65

Madison, WI

Primerica Advisors

Kayla Wheeler is a financial advisor with Primerica Advisors in Madison, WI, holding Series 63 and Series 65 credentials and one year of industry experience. She has worked at Primerica Advisors since 2024 and has prior experience with Spectrum Brands and Lakeside Foods. Outside of advisory work, she is involved in sales of loan products and home-related services through affiliated companies. Primerica Advisors provides discretionary asset management through its Lifetime Investment Program, serving individual and high-net-worth clients with model-delivery strategies and limited discretionary separately managed account options. The firm curates third-party asset managers and delegates trading responsibilities to BNY Mellon Advisors, operating primarily on a tiered wrap-fee basis.

ESG / Sustainable investing Tax-loss harvesting Income planning
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Thomas P

Series 65

Brookfield, WI

Annex Wealth Management, LLC

Thomas Phillipsen is a Series 65 licensed advisor at Annex Wealth Management, LLC with experience beginning in 2024. His prior work includes roles at Associated Bank and JJ Keller & Associates, as well as experience at Ripon College. Annex Wealth Management is an SEC-registered advisory firm managing approximately $8.05 billion for about 9,800 clients, including high-net-worth individuals, pension plans, charitable organizations, and corporate entities. The firm utilizes a team-oriented investment process based on a core-and-tactical framework and offers comprehensive wealth management, discretionary portfolio management, retirement consulting, and online goals-based services.

Wealth management Options & derivatives strategies Tax-loss harvesting Retirement income strategy Founder/Business Owner Retired Executive HENRY (High Earners, Not Rich Yet) Mid-Career Professionals
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Jeffrey S

Series 63, Series 65

Mequon, WI

Charles Schwab

Jeffrey Schnoor is a financial advisor with Charles Schwab in Mequon, WI, holding Series 63 and Series 65 licenses and with 34 years of industry experience. He worked at Johnson Wealth Inc. for 20 years before joining Charles Schwab in 2022. Charles Schwab & Co., Inc. serves primarily high- and ultra-high-net-worth individuals through its Schwab Wealth Advisory wrap fee program and affiliated managed-account and financial planning services, offering both non-discretionary investment guidance and access to discretionary separately managed accounts.

Private / alternative investments Real estate investing Multi-state taxation College savings (529s, UTMA, etc.)
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Jonathan S

Series 65

Stevens Point, WI

Summit Financial, LLC

Jonathan Steffen is a financial advisor at Summit Financial, LLC with 11 years of industry experience and holds a Series 65 designation. He has previously worked at Silvertree, LLC and Brookstone Capital Management. Outside of advising, he is involved in business consulting on tax savings strategies and offers insurance products as a licensed broker. Summit Financial, LLC is an SEC-registered, multi-team advisory firm managing approximately $26.35 billion in assets for around 17,800 clients. The firm offers a range of investment advisory services, including discretionary and consultative portfolio management programs, financial planning, and access to alternative investments.

Tax-loss harvesting Private / alternative investments Retirement plans for business owners (SEP, solo 401k) Business exit / sale strategy General estate planning guidance Founder/Business Owner Executive
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Andrew R

Series 63, Series 65

Wauwatosa, WI

Packerland Brokerage Services, Inc.

Andrew Richman is a financial advisor with Packerland Brokerage Services, Inc. in Wauwatosa, WI, holding Series 63 and Series 65 licenses and bringing 28 years of industry experience. He has been with Packerland Brokerage Services since 2009. In addition to his advisory role, he is involved in insurance sales, focusing on life, health, long-term care, fixed, and indexed annuities. Packerland Brokerage Services, Inc. serves individuals, charities, corporations, and retirement plan sponsors with financial planning, portfolio management, and advisory program access through various platforms and account management options. The firm is dually registered as an SEC investment adviser and FINRA broker-dealer, managing over $900 million in client assets, and offers both brokerage and advisory implementation pathways.

Retirement income strategy Options & derivatives strategies Wealth management

Charles P

Series 63, Series 65

Easton, MD

Merrill

Charles Pritchett is a Senior Financial Advisor with Merrill Lynch Wealth Management. He focuses on developing personalized financial plans that address clients' unique ambitions, including education funding, retirement lifestyle planning, and long-term family goals. His approach emphasizes simplicity and transparency in investment management to help clients navigate the complexities of wealth planning. Mr. Pritchett holds both a Bachelor's and a Master's degree from Salisbury University. He holds the designation of Personal Investment Advisor (PIA). Outside of his professional work, he enjoys baseball, gardening, and spending time with his family.

College savings (529s, UTMA, etc.) General retirement planning Medicare planning Wealth management
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Mark P

Series 66

Conneaut Lake, PA

Lakeland Investor Services, Inc.

Mark Petro is a financial advisor at Lakeland Investor Services, Inc. in Conneaut Lake, PA, with 24 years of industry experience. He holds a Series 66 designation and has worked at the firm since 2002. He is also president of Lakeland Insurance Services, LLC, a business he established to handle insurance sales and related operations. Lakeland Investor Services provides fee-based wealth advisory and investment management services to individuals, multi-generational families, high-net-worth clients, small non-profit organizations, small businesses, and qualified retirement plans. The firm offers comprehensive financial planning, portfolio management, and uses a variety of analytical approaches including fundamental, technical, and Monte Carlo modeling.

Social Security optimization Retirement income strategy Annuities
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David D

Series 65

Bellevue, WA

Leverage Planners Wealth Management, LLC

David Donhoff is a financial advisor at Leverage Planners Wealth Management, LLC in Renton, WA, with nine years of industry experience. He holds a Series 65 designation and has been with Leverage Planners since 2017. Prior to this, he has been involved with No Bull Financial LLC since 2001, where he also engages in insurance sales and services on a limited basis. Leverage Planners primarily serves individual clients, offering discretionary asset management along with comprehensive financial planning and consulting. The firm emphasizes educational outreach through newsletters and public seminars, and employs a combination of fundamental, technical, and cyclical analysis in investment decisions, supported by a third-party sub-advisor for portfolio implementation and tax-efficient strategies.

Retirement income strategy Medicare planning General retirement planning Annuities General tax planning
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Thomas V

Series 63, Series 65, Series 66

Hancock, NH

Monadnock Retirement Solutions, LLC

Thomas Villeneuve is a financial advisor with Monadnock Retirement Solutions, LLC, holding Series 63, 65, and 66 licenses and bringing 18 years of industry experience. He has held prior roles at Citizens Securities, NYLIFE Securities, New York Life Insurance Company, and Baltimore Life. Outside of advisory work, he serves as a part-time instructor providing basic financial education at UNH Cheshire Academy of Lifelong Learning. Monadnock Retirement Solutions offers comprehensive financial planning and investment management to individual and high-net-worth clients, focusing on written financial plans and ongoing portfolio oversight. The firm manages client assets primarily on a non-discretionary basis and incorporates insurance and long-term care reviews, 401(k) evaluations, and tailored model portfolios through third-party sub-advisers.

General retirement planning Income planning Medicare planning College savings (529s, UTMA, etc.)
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Jeffrey M

CFP®, Series 66

Shrewsbury, MA

Meenes Wealth Partners

Jeffrey Meenes is a CFP® and Series 66 licensed financial advisor with 14 years of industry experience. He has worked at Blueprint Financial Planning, LLC since 2010. Meenes operates as the sole advisor at Meenes Wealth Partners in Shrewsbury, MA. Meenes Wealth Partners provides flat-fee, fiduciary wealth management and comprehensive financial planning primarily for pre-retiree and retiree households. The firm emphasizes evidence-based investment strategies focused on global diversification, tax-aware management, and client-approved, non-discretionary portfolio implementation.

General retirement planning Retirement income strategy Social Security optimization Medicare planning Tax-loss harvesting Retired Approaching retirement Retired

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