Top social Security optimization financial advisors in Skokie, 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.

You might need a Social Security optimization advisor if you're approaching retirement and want to maximize your monthly benefits without triggering penalties or reducing your spouse's benefits. A common mistake is claiming benefits too early or without considering your full work history, which can leave money on the table.

  • Claiming strategy expertise. Look for advisors who explain how to time your benefits to balance immediate income needs with long-term gains.
  • Spousal and survivor benefits. Confirm they understand how to coordinate benefits between you and your spouse to optimize household income.
  • Impact of work history. Ask how they factor in your earnings record and potential future income when recommending claim ages.
  • Coordination with other income. Ensure they consider how your Social Security benefits interact with pensions or other retirement income sources.

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

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Julian V

Series 63, Series 66

Skokie, IL

Northern Trust Securities, Inc.

Julian Van Ostrand is a financial advisor with Northern Trust Securities, Inc. in Skokie, IL, holding Series 63 and Series 66 credentials and bringing 21 years of industry experience. He has been with Northern Trust Securities since 2008. Northern Trust Securities, Inc. is an SEC-registered investment adviser and FINRA-registered broker-dealer that provides discretionary portfolio management through a model-driven wrap fee program serving high-net-worth individuals, retail investors, and institutional clients. The firm offers a variety of managed account solutions and combines advisory, brokerage, and custody services, including access to both proprietary and third-party investment products.

Passive / index investing Active portfolio management ESG / Sustainable investing Tax-loss harvesting Founder/Business Owner Executive
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Gabriel R

Series 63, Series 65

Skokie, IL

Fidelity

Gabriel Reyes is a financial advisor at Fidelity with 14 years of industry experience. He holds the Series 63 and Series 65 credentials and has worked at firms including Princor Financial Group, Principal Life Insurance Co, and PNC Wealth Management. Reyes is also an officer of Invictus Capital Holdings, LLC, a passive investment-related entity. Fidelity’s Strategic Advisers LLC provides investment management and advisory services to retail and institutional clients, employing a blend of proprietary fundamental research, quantitative analysis, and algorithmic portfolio construction to deliver model portfolios across various investment vehicles.

Charitable giving & philanthropy Active portfolio management
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Leonard F

Series 65

Skokie, IL

HealthQuant Associates LLC

Leonard Fensterheim is a Series 65-licensed financial advisor with 11 years of industry experience. He is the principal of HealthQuant Associates LLC, where he has worked since 2014. In addition to his advisory role, he serves as Director of Clinical Outcomes and Analytics at Catamaran Corporation and is a partner at Highbeam Capital LLC, where he dedicates time to research on biotechnology and healthcare investments. HealthQuant Associates LLC is a state-registered investment adviser that provides discretionary portfolio management with an investment approach combining fundamental, technical, and cyclical economic analysis. The firm focuses on tailored portfolios primarily in the healthcare and life-sciences sectors, employing strategies ranging from long-term buy-and-hold to shorter-term trading, including the use of short sales and options.

Active portfolio management
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Merrick R

Series 66

Skokie, IL

Guardian Life

Merrick Robison is a financial advisor at Guardian Life with one year of industry experience. He holds the Series 66 designation and has worked at Guardian Life and Park Avenue Securities since 2024. Outside of his advisory role, he operates a non-investment-related business called Merrick R - Rover Services. Park Avenue Securities LLC, a subsidiary of The Guardian Life Insurance Company of America, provides brokerage and investment advisory services to individuals, corporate and retirement plan sponsors, charitable organizations, and businesses. The firm offers tailored client relationships through a combination of advisor-led discretionary management and model-based strategies, utilizing proprietary programs and third-party platforms.

Business exit / sale strategy Tax-loss harvesting Retirement plans for business owners (SEP, solo 401k) Charitable giving & philanthropy Founder/Business Owner Executive Financial Professional Approaching retirement Established Professionals Mid-Career Professionals
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Ari L

Series 63, Series 65

Skokie, IL

Baldwin Wealth Partners, LLC

Ari Lazar is a financial advisor at Baldwin Wealth Partners, LLC with eight years of industry experience. He holds the Series 63 and Series 65 designations. Prior to joining Baldwin Wealth Partners, he worked at Levin Capital Strategies and RGA Investment Advisors. Outside of his advisory role, Lazar coaches and judges high school gymnastics in Illinois. Baldwin Wealth Partners provides investment advisory and financial planning services to a diverse range of clients, including individuals, trusts, charitable organizations, and pooled investment vehicles. The firm employs a combined top-down macro framework and bottom-up fundamental research, managing portfolios across five core asset classes with attention to ESG factors and offering specialized services such as management of private funds and tax-aware equity strategies.

ESG / Sustainable investing Private / alternative investments Real estate investing Concentrated stock management Wealth management Founder/Business Owner Executive Established Professionals
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Willie M

Series 63, Series 66

Cary, NC

Equitable Advisors

Willie Myles is a financial advisor with Equitable Advisors in Cary, NC, holding Series 63 and Series 66 licenses and bringing 16 years of industry experience. He has worked at Equitable Advisors since 2016, previously serving at Axa Advisors and MSI Financial Services. Outside of advising, he is a co-chairman of a fundraising campaign for Alpha Light Fund Inc., a nonprofit focused on renovating the House of Alpha. Equitable Advisors serves a range of clients including individuals, pension plans, corporations, and charitable organizations, providing financial planning, retirement consulting, and asset management through a network of representatives and third-party managers. The firm offers various investment vehicles and ERISA fiduciary services, relying on third-party program sponsors and an affiliation with a publicly traded parent company.

Retirement plans for business owners (SEP, solo 401k) Business exit / sale strategy Concentrated stock management Equity Recipients (RS/RSU, SOP, ESPP) Long-term care insurance Founder/Business Owner Retired Executive Approaching retirement Sandwich Generation
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Stavroula K

Series 63, Series 65

Linwood, NJ

Ameriprise

Stavroula Koutsfetsoulis is a financial advisor at Ameriprise with 25 years of industry experience. She holds Series 63 and Series 65 licenses and has been with Ameriprise and its affiliated entities since 2011. In addition to her advisory role, she is involved in fiduciary activities as an attorney-in-fact (power of attorney). Ameriprise is a large institutional firm that provides retirement-income planning services primarily to individuals with substantial investable assets. The firm combines research, modeling, and tax-efficiency analysis to deliver written recommendation reports through a centralized consulting team, focusing on tailored retirement income strategies.

Retirement income strategy Income planning Social Security optimization Retirement withdrawal strategies Approaching retirement
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Cassandra S

Series 63, Series 65

Plano, TX

Financial & Tax Architects, LLC

Cassandra Sanchez is a financial advisor at Financial & Tax Architects, LLC with seven years of industry experience. She holds Series 63 and Series 65 licenses and has previously worked at Fisher Investments, TIAA, US Health Advisors, and various other firms. Sanchez also had involvement with Drunken Donkey, reflecting experience outside the financial sector. Financial & Tax Architects provides discretionary portfolio management and financial planning primarily for individual and high-net-worth clients, focusing on those nearing or in retirement. The firm offers proprietary “Private Wealth Strategies” that use ETFs, individual securities, and trend-aware rebalancing, with accounts reviewed monthly and customizable strategies to meet client needs.

Retirement income strategy Social Security optimization Annuities Income planning General tax planning Retired
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Keith E

CFP®

Pittsburgh, PA

Keith L. Eliou, CFP

Keith Eliou is the principal of Keith L. Eliou, CFP, an investment management firm based in Pittsburgh, PA. He holds the CFP® designation and has one year of experience as a financial advisor. In addition to his advisory role, he practices law focusing on elder law and real estate and is involved in insurance, mortgage lending, and real estate brokerage businesses. The firm primarily serves pooled vehicles and institutional accounts, offering portfolio management, retirement plan services, and financial planning. It utilizes an open-architecture investment approach with third-party money managers and employs multiple analytical methods and strategies, conducting annual account reviews.

Social Security optimization Retirement income strategy Cash flow / budgeting Charitable giving tax strategies Business exit / sale strategy Founder/Business Owner
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Charles P

CFP®, Series 63, Series 65

San Rafael, CA

WealthSpire Advisors

Charles Pyfer III is a CFP® professional with 19 years of industry experience, currently serving at Wealthspire Advisors since 2024. Prior to this, he spent 15 years at Private Ocean. Wealthspire Advisors provides wealth management, investment advisory, financial planning, and family office support to a diverse client base including individuals, corporations, retirement plans, and nonprofit organizations. The firm employs a relationship-driven, customized investment approach that emphasizes diversified, institutional-style asset allocation and utilizes a range of investment vehicles and third-party platforms for comprehensive portfolio management.

Retirement income strategy Social Security optimization Roth conversion strategy Tax-loss harvesting Private / alternative investments Founder/Business Owner Retired Mid-Career Professionals Established Professionals
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