CFP®-certified financial advisors working with retirees in Pittsfield, MA

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 transitioning into retirement or already retired and looking to manage your income and assets effectively. Without focused guidance, it's easy to overlook how taxes, healthcare costs, and withdrawal strategies interact, which can reduce your financial security.

  • Income sequencing. Ask how they plan your withdrawals to balance tax impact and cash flow needs over time.
  • Healthcare cost planning. Confirm they consider Medicare premiums and potential long-term care expenses in your budget.
  • Tax surtax awareness. In Massachusetts, income above certain levels faces extra surtaxes; check how they address this in your plan.
  • Legacy considerations. Discuss how they incorporate your wishes for passing assets to heirs while managing tax consequences.

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

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Elizabeth A

Series 63, Series 65

Pittsfield, MA

Eagle Strategies (NY Life)

Elizabeth Ariazi is a financial advisor with Eagle Strategies (NY Life) based in Pittsfield, MA, holding Series 63 and Series 65 licenses and with 17 years of industry experience. She has worked with NYLIFE Securities LLC and New York Life Insurance Company since 2008, and joined Eagle Strategies LLC in 2021. Outside of advising, she manages short-term rentals of her primary residence through Airbnb. Eagle Strategies serves a broad mix of individual and institutional clients, providing financial planning, investment management, and retirement-plan advisory services through a large network of affiliated investment adviser representatives. The firm emphasizes tailoring recommendations to client objectives and manages the majority of its assets on a non-discretionary basis.

Retirement plans for business owners (SEP, solo 401k) Business exit / sale strategy General retirement planning Retirement income strategy Founder/Business Owner Executive
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Michael F

Series 63, Series 65

Pittsfield, MA

LPL Financial

Michael Fazio is a financial advisor with LPL Financial in Pittsfield, MA, holding Series 63 and Series 65 credentials and bringing 24 years of industry experience. He has served as Senior Vice President at Greylock Federal Credit Union since 2008. LPL Financial is an SEC-registered investment adviser and broker-dealer serving individuals, retirement plans, banks, credit unions, corporations, and charitable organizations through a national network of investment adviser representatives. The firm offers a range of financial planning and advisory programs, including discretionary and non-discretionary management, model portfolios, and retirement plan consulting.

College savings (529s, UTMA, etc.)
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William K

CFP®, Series 63, Series 65

Pittsfield, MA

Raymond James Financial

William Kirby is a CFP® with 50 years of experience in the financial industry, currently serving at Raymond James Financial Services Advisors Inc. He previously worked for Wells Fargo Advisors for 12 years. Kirby is chair of the investment committee for the Berkshire Community College Foundation. Raymond James Financial Services Advisors, Inc. provides financial planning, investment consulting, and advisory services to a diverse client base, including individual and high-net-worth clients, institutions, and charitable organizations. The firm offers tailored, non-discretionary planning and consulting using analytical tools and supports its clients through various advisory programs.

Wealth management Tax strategies for small businesses Business succession planning General estate planning guidance Founder/Business Owner Executive
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Darrell C

Series 66

Pittsfield, MA

Raymond James & Associates

Darrell Colvin is a financial advisor at Raymond James & Associates with three years of industry experience. He holds a Series 66 designation and has prior experience with Prudential Insurance Company of America, Guardian Life, and Wayfair L.L.C. Colvin volunteers with the Berkshire Theatre Group in Pittsfield, MA. Raymond James & Associates is a large, dually registered broker-dealer and SEC-registered investment adviser managing approximately $501 billion in assets. The firm serves a diverse client base including individuals, institutions, and municipal entities, offering financial planning and investment consulting through a range of portfolio management styles and affiliated research.

General retirement planning Retirement income strategy Business succession planning Founder/Business Owner Executive
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Kevin O

CFP®, Series 63, Series 65

Pittsfield, MA

Commonwealth Financial Network

Kevin O'Donnell Jr. is a CFP® professional with 28 years of experience in the financial industry. He has been affiliated with Commonwealth Financial Network and Berkshirebanc Investment Services since 2006. His activities include fixed insurance sales at his branch location. Commonwealth Financial Network is a dual-registered broker/dealer and investment adviser supporting a national network of approximately 2,900 advisors and managing over $212 billion in client assets. The firm provides a comprehensive adviser-support platform with access to managed-account programs, third-party asset managers, and custody services.

Passive / index investing Active portfolio management Tax-loss harvesting Wealth management Retirement income strategy Founder/Business Owner Executive Retired
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Craig M

Series 63, Series 65

Columbia, SC

Capital Investment Advisory Services, LLC

Craig Mcdaniel Jr. is a financial advisor with Capital Investment Advisory Services, LLC in Columbia, SC. He holds Series 63 and Series 65 licenses and has 13 years of industry experience. He has been with Capital Investment Group, Inc. and The McDaniel Corporation since 2012. Outside of his advisory role, he is involved in life insurance sales and serves as an independent agent for annuities and related products. Capital Investment Advisory Services, LLC provides investment advisory and supervisory services to individuals, retirement plans, corporations, trusts, estates, and charitable organizations. The firm offers customized investment management through discretionary mandates, third-party managers, and private-label model portfolios, using a blend of analytical methods with ongoing portfolio monitoring.

Active portfolio management Retirement plans for business owners (SEP, solo 401k) Annuities Options & derivatives strategies Founder/Business Owner Retired
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Wesley P

Series 63, Series 66

Fort Worth, TX

Wells Fargo Clearing

Wesley Pool is a financial advisor at Wells Fargo Clearing with 15 years of industry experience. He holds Series 63 and Series 66 licenses and previously worked at JPMorgan Securities LLC for seven years. Outside of finance, he has been involved with #TagMeBro LLC and Fry Street Public House. Wells Fargo Advisors is a national securities firm serving individual, corporate, and institutional clients with investment advisory services, financial planning, and retirement plan consulting. The firm manages approximately $671 billion in assets and offers both brokerage and advisory solutions.

Retired Founder/Business Owner
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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 and previously at AXA Advisors, LLC. Outside of his advisory work, he serves as co-chairman of a fundraising campaign for the nonprofit Alpha Light Fund Inc., focused on renovating the House of Alpha. Equitable Advisors serves a diverse client base including individual, high-net-worth, retirement plan, corporate, charitable, and institutional clients, offering financial planning, broker-dealer services, insurance distribution, and access to third-party asset management programs. The firm operates as both an SEC-registered investment adviser and broker-dealer, leveraging LPL-sponsored programs and endorsed TAMPs to deliver advisory and brokerage solutions.

Retirement income strategy Social Security optimization Founder/Business Owner Retired Executive Approaching retirement Baby Boomers (Born 1946-1964)
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Hassan A

Series 65, Series 63

Rockville, MD

LPL Financial

Hassan Al Kadhimi is a financial advisor at LPL Financial with two years of industry experience. His work history includes roles at J.P. Morgan Securities LLC and JP Morgan Chase Bank, N.A. He is registered with Series 65 and Series 63 licenses. LPL Financial is an SEC-registered investment adviser and broker-dealer that serves a wide range of clients, including individuals, retirement plans, banks, and charitable organizations. The firm offers financial planning, advisory programs, retirement consulting, and brokerage services through a national network of investment adviser representatives.

College savings (529s, UTMA, etc.)
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Amanda S

Series 66

Ft. Wayne, IN

Raymond James & Associates

Amanda Scheele is a financial advisor at Raymond James & Associates with 15 years of industry experience. She holds the Series 66 designation and previously worked at Wells Fargo Clearing and Wells Fargo Advisors LLC. Outside of her advisory role, she is involved with Lucky Duck, a venture she has been part of since 2025. Raymond James & Associates, Inc. is a large registered broker-dealer and SEC-registered investment adviser managing approximately $501 billion in assets. The firm serves a diverse client base, including individuals, institutions, and municipal entities, offering financial planning, non-discretionary investment consulting, and municipal advisory services.

General retirement planning Retirement income strategy Business succession planning Founder/Business Owner Executive
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Sarah C

CFP®, Series 63, Series 65

Boston, MA

Santander Securities LLC

Sarah Currier Barrella is a CFP® professional with 26 years of experience in financial advisory services. She currently works at Santander Securities LLC and Santander Bank, NA, having previously held positions at TD Bank and Citizens Securities, Inc. Barrella is based in Boston, MA. Santander Securities LLC serves a broad retail client base with approximately $3.14 billion in regulatory assets under management across 10,800 client relationships. The firm offers investment advisory services, portfolio management through wrap-fee programs, and financial planning, operating both as a registered investment adviser and a FINRA-registered broker-dealer.

ESG / Sustainable investing Tax-loss harvesting General retirement planning Income planning Founder/Business Owner
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Elanna G

CFP®, Series 66

Cleveland, OH

Cambridge Investment Research Advisors

Elanna Gould is a CFP® professional with six years of experience, currently advising at Cambridge Investment Research Advisors in Cleveland, OH. Her background includes roles at PepsiCo and The Cleveland Clinic Lerner Research Center, as well as academic experience at The Ohio State University. She is also an independent insurance agent for various companies. Cambridge Investment Research Advisors serves a broad client base, including individuals, retirement plans, and charitable organizations, offering financial planning, investment management, and retirement advisory services through a network of independent professionals. The firm provides a range of portfolio management options, proprietary and third-party strategies, and various custody platforms tailored to client objectives.

Wealth management Retirement plans for business owners (SEP, solo 401k) Retirement income strategy Annuities Self-Employed
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Ethan S

CFP®, Series 65

Auburn Hills, MI

Plante Moran FInancial Advisors

Ethan Siekkinen is a CFP® and holds a Series 65 license with Plante Moran Financial Advisors. He has one year of industry experience and previously worked at J Wilson Wealth Management. Outside of financial advising, he has experience in the lawn care business with Rizzo Lawn Care. Plante Moran Financial Advisors serves a diverse client base including individuals, institutions, trusts, estates, and charitable organizations. The firm provides investment advisory, financial planning, and estate-planning services, utilizing a range of investment strategies and managing both discretionary and non-discretionary assets.

Options & derivatives strategies Private / alternative investments Concentrated stock management Wealth management Executive Founder/Business Owner
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Jace H

CFP®, Series 63, Series 66

Rockwall, TX

Rockwall Wealth Management

Jace Hart is a CFP® with nine years of industry experience and currently serves as a financial advisor at Rockwall Wealth Management. His prior experience includes roles at Leo Wealth, LPL Financial, and Fidelity Brokerage Services. Rockwall Wealth Management provides portfolio management, financial planning, and consulting services to individuals, trusts, plans, charitable organizations, and businesses. The firm emphasizes diversified, low-cost ETF model portfolios with a focus on tax efficiency, liquidity, and systematic macro tilts, offering both traditional and advanced investment strategies tailored to client objectives.

Active portfolio management Options & derivatives strategies Private / alternative investments Retirement plans for business owners (SEP, solo 401k) Retirement income strategy
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Jeffrey M

CFP®, ChFC®, Series 66

Greenville, DE

Investment Management & Planning LLC

Jeffrey Macdonald is a CFP® and ChFC® with 17 years of industry experience. He has been with Investment Management & Planning LLC since 2010 and is also affiliated with LPL Financial LLC. Investment Management & Planning LLC provides fee-based investment advisory and comprehensive financial planning primarily for individual and high-net-worth clients, offering portfolio management on both discretionary and non-discretionary bases. The firm emphasizes ongoing account supervision and individualized asset allocation, often utilizing LPL-sponsored platforms and model portfolios.

General retirement planning Business succession planning Tax strategies for small businesses Wealth management Founder/Business Owner Retired Mid-Career Professionals Established Professionals

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