Top social Security optimization financial advisors in Billings, MT

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 be considering Social Security optimization if you're approaching retirement and want to maximize your monthly benefits. A common mistake is claiming benefits too early or without considering spousal and survivor options, which can reduce your lifetime income.

  • Claiming strategy nuances. Ask how they tailor claiming ages and benefit types to your unique work history and family situation.
  • Coordination with other income. Confirm they consider how Social Security interacts with your pensions, investments, and tax situation.
  • Spousal and survivor benefits. Ensure they evaluate options beyond your own benefits to boost household income.
  • Longevity planning. Check if they model your benefits over your expected lifespan to avoid running short of income.

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

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Corey S

Series 66

Billings, MT

Stapleton Financial Group

Corey Stapleton is the principal advisor at Stapleton Financial Group, an independent firm based in Billings, Montana. He holds the Series 66 designation and has 29 years of industry experience. He has led Stapleton Financial Group since 2016. Stapleton Financial Group provides discretionary investment management and financial planning primarily for individuals and high-net-worth clients. The firm customizes portfolios based on client objectives and risk tolerance, emphasizing diversification and cost considerations while offering services that include collaboration with clients' attorneys and accountants.

General retirement planning Wealth management Cash flow / budgeting Disability insurance

Kaleb H

Series 66

Billings, MT

Edward Jones

Kaleb Haub is a financial advisor at Edward Jones in Billings, MT, holding a Series 66 designation with one year of industry experience. Prior to joining Edward Jones, he worked at Word of Life and Mattress King for several years. Edward Jones is a full-service wealth management firm serving over four million individual and institutional clients. The firm offers a range of investment strategies including discretionary and non-discretionary wrap fee programs, separately managed accounts, and affiliated mutual funds, supported by a nationwide network of more than 23,000 financial advisors.

Charitable giving & philanthropy Business ownership considerations Business succession planning Retirement income strategy Wealth management Founder/Business Owner
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Ben K

Series 63, Series 66

Billings, MT

Principal Financial Services

Ben Kazmierski is a financial advisor with Principal Financial Services, holding Series 63 and Series 66 licenses and bringing 26 years of industry experience. He has been with Principal Securities Inc and Principal Financial Group since 2012. Outside of his advisory role, he co-owns an escape room business and teaches continuing education through Northstar Educational Services. Principal Securities provides brokerage and registered investment advisory services to a diverse client base, including individual investors, retirement plans, trusts, and military personnel. The firm offers direct advisory programs, financial planning, retirement plan consulting, and access to third-party money manager solutions.

Retired Founder/Business Owner
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Daniel K

Series 63, Series 65

Billings, MT

Primerica Advisors

Daniel Krug is a financial advisor with Primerica Advisors in Billings, MT, holding Series 63 and Series 65 licenses and with 25 years of industry experience. He has been with Primerica Advisors since 2001 and also affiliated with Primerica Financial Services since 2000. Outside of his advisory role, he is involved in business activities related to Primerica Mortgage and referrals for home security and automation products. Primerica Advisors manages a wrap-fee asset management program serving primarily individual investors, including both non-HNW and high-net-worth clients, as well as corporate and charitable clients. The firm employs model-based investment strategies created by unaffiliated asset managers and supports trade execution and custody through BNY Mellon Advisors and Pershing.

ESG / Sustainable investing Tax-loss harvesting Income planning
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Douglas M

Series 66

Billings, MT

LPL Financial

Douglas Mullowney is a Series 66-licensed financial advisor with LPL Financial, based in Billings, Montana, with 28 years of industry experience. He previously worked at Waddell & Reed, Inc. for 24 years and held roles with various insurance carriers for over two decades. Mullowney is also involved with Montana Tax Group, PLLC, a business entity for tax and investment purposes. LPL Financial is a national broker-dealer and SEC-registered investment adviser offering advisory and brokerage services to individuals, retirement plan participants, banks, trust companies, and institutions. The firm provides financial planning, portfolio management, and institutional platforms, supporting advisors with advanced research tools and a broad range of investment strategies.

Wealth management Retirement income strategy College savings (529s, UTMA, etc.) Tax-loss harvesting Annuities Retired Founder/Business Owner Executive
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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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