Top general retirement planning financial advisors in Bennington, VT

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.

Planning for retirement in Bennington, VT often means preparing for healthcare access challenges due to the area's rural nature and aging population. Without careful planning, you might underestimate the costs and logistics of medical care in retirement.

  • Healthcare access planning. Confirm how the advisor incorporates local healthcare availability and costs into your retirement plan.
  • Income sustainability. Ask how they balance your income sources to cover both expected and unexpected expenses over a long retirement.
  • Social Security timing. Discuss strategies for when to claim benefits to maximize your lifetime income.
  • Inflation impact. Ensure they consider how rising costs, especially healthcare, affect your retirement budget over time.

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

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Shawn L

Series 63, Series 65

Bennington, VT

Commonwealth Financial Network

Shawn Leonard is a financial advisor with Commonwealth Financial Network based in Bennington, VT. He holds Series 63 and Series 65 licenses and has 22 years of industry experience. Prior to his current role, he worked at MountainOne Bank’s investment group for 14 years. Leonard also engages in fixed insurance sales as a minor part of his business activities. Commonwealth Financial Network is a registered investment adviser serving a national network of approximately 2,950 advisors and their clients. The firm provides a range of advisory programs and operational support, including discretionary model portfolios managed by its Investment Management and Research team.

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

Ryley G

Series 66

Bennington, VT

Edward Jones

Ryley Gaudreau is a financial advisor at Edward Jones in Bennington, VT, holding a Series 66 designation with 18 years of industry experience. He has been with Edward Jones since 2008. Edward Jones is a full-service wealth management firm serving over four million individual and institutional clients, including pension plans, corporate clients, and charitable organizations. The firm manages approximately $1.01 trillion in assets and offers a range of advisory services under a fiduciary standard, with a large nationwide network of financial advisors and branch offices.

Retirement income strategy General retirement planning Wealth management Business exit / sale strategy Multi-generational wealth transfer Retired Founder/Business Owner Executive
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Jason J

Series 63, Series 65

Colchester, VT

Equity Services, inc.

Jason Jeffers is a financial advisor at Equity Services, Inc. with 27 years of industry experience. He holds Series 63 and Series 65 credentials and has worked at National Life Group, LPL Financial, People's United Advisors, and People's Securities. Jeffers owns J&S Wealth Advisors, a consulting business focused on non-financial services guidance. Equity Services, Inc. (ESI Financial Advisors) provides financial planning, consulting, and asset management services to individuals, corporations, trusts, estates, charitable organizations, and employer retirement plans. The firm offers multiple advisory platforms, using third-party asset managers and model portfolios, and combines long-term strategies with options for shorter-term trading.

Retirement plans for business owners (SEP, solo 401k) Options & derivatives strategies Income planning Founder/Business Owner Retired Executive
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Daryl S

CFP®, Series 66

North Bennington, VT

Williams Financial, LLC

Daryl Spirka is a CFP® professional with 20 years of industry experience, currently serving at Williams Financial, LLC since 2015. He has prior experience at Lonergan And Thomas Insurance and has operated his own CPA practice since 2002. Outside of financial services, he owns and operates Passion 4 Sports, a sporting goods business in Wilmington, VT. Williams Financial, LLC provides fee-only financial planning, investment management, and pension consulting services to individuals, trusts, estates, and business entities. The firm uses a long-term investment approach combined with tactical asset allocation and multiple analytical methods, offering both integrated wealth management and digital portfolio options.

General retirement planning Tax strategies for small businesses Charitable giving & philanthropy Cash flow / budgeting
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Brian M

CFP®, Series 63, Series 66

Bennington, VT

Bennington Financial Planning Group

Brian McKenna is a CFP® professional with 19 years of industry experience, currently serving as a financial advisor at Bennington Financial Planning Group since 2010. He also maintains a role with D.B. McKenna & Co., Inc., a broker-dealer firm, dedicating half of his time to each business. In addition to his advisory work, McKenna is a member of the Bennington Redevelopment Group LLC, which focuses on revitalizing the downtown Bennington community, and he provides tax preparation services. Bennington Financial Planning Group offers portfolio management and financial planning services to individuals, trusts, estates, charitable organizations, businesses, and government clients. The firm employs a fundamental analysis approach supplemented by technical and cyclical methods, utilizing both long- and short-term trading strategies including covered-call writing, with accounts reviewed regularly and discretionary management available.

College savings (529s, UTMA, etc.)
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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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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

Lori F

Series 66

East Lansing, MI

Edward Jones

Lori Fell is a financial advisor with Edward Jones in East Lansing, MI, holding a Series 66 designation and 16 years of industry experience. She has been with Edward Jones since 2009. Outside of her advisory role, she owns a business focused on property management. Edward Jones is a full-service wealth management firm serving individual and institutional clients, with over $1 trillion in assets under management and a nationwide network of more than 23,000 financial advisors. The firm offers a range of advisory programs and investment strategies, including discretionary and non-discretionary wrap fee options, tax-efficient services, and affiliated mutual funds.

General retirement planning Multi-generational wealth transfer Retired Founder/Business Owner Executive
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Kenneth B

Series 63, Series 65

Portland, ME

Headinvest

Kenneth Blaschke is a financial advisor at HeadInvest in Portland, ME, holding Series 63 and Series 65 licenses with 16 years of industry experience. He has been with HeadInvest since 2009. HeadInvest serves a diverse range of clients, including individuals, trusts, endowments, and government entities, providing discretionary portfolio management and financial planning. The firm employs a holistic, asset-allocation driven approach, combining fixed-income selection with low-cost ETFs and emphasizing tax efficiency.

Wealth management General retirement planning Tax strategies for small businesses Founder/Business Owner Retired
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Michael I

Series 63, Series 65

Livingston, NJ

Raymond James Financial

Michael Ipp is a financial advisor with Raymond James Financial, holding Series 63 and Series 65 designations and bringing 42 years of industry experience. He has been with Raymond James Financial Services Advisors since 2010 and serves as an independent contractor for 1792 Wealth Advisors. Raymond James Financial Services Advisors provides financial planning, investment consulting, and advisory services to a diverse client base, including individuals, high-net-worth clients, corporations, and institutional clients. The firm offers tailored, non-discretionary planning and uses analytical tools to support client decision-making, while also maintaining specialized programs such as municipal advisory services and SIMPLE IRA Employer Advisory & Consulting Services.

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