Our Team

Our Team

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Cheryl A. Costa, MBA, CFP®



Cheryl is the Founding Principal of Woodside Wealth Management LLC. She began her career in financial planning and investment management in the late ‘90s after graduating from Worcester Polytechnic Institute and working as an engineer for the MITRE Corporation. She holds a Master’s degree in Business Administration from Boston University and is a CERTIFIED FINANCIAL PLANNER ™. 

Cheryl has 20 years of experience advising clients in all areas of wealth management.  Areas of particular interest to her include taxes, portfolio design, and saving for college. Cheryl’s specialty is helping clients in their 40s and 50s save for retirement and helping retired clients map out a supportable spending plan that assures income is available for a retirement that may span many decades.

Cheryl is committed to the fee-only comprehensive planning model and has been a member of the National Association of Personal Financial Advisors (NAPFA) since 2002. She served on the Northeast Region Board of NAPFA from 2005-2010 holding the positions of Membership Director, Region President and Region Chair.  In 2015, Cheryl completed a three-year term on NAPFA’s National Board where she chaired the organization’s Women’s Initiative (WI).  Cheryl has been a member of the Financial Planning Association (FPA) for over 15 years and served on the Board of the FPA of Massachusetts from 2011 through 2012.  Cheryl is currently serving a three-year term as a member of the CFP Board's Disciplinary and Ethics Commission and she was also recently chosen to be a CFP® Ambassador for the state of Massachusetts.  In this role, she educates the public and the media about how CFP ® professionals and financial planning can help consumers achieve their financial goals. 

Cheryl’s financial planning and investment management expertise is widely recognized.  She was named one of the “Top 50 Women in Wealth Management” by Wealth Manager Magazine and she wrote “Managing Your Money”, a personal finance blog for the Boston Globe for several years.  She has been quoted in the Wall Street Journal, New York Times, Washington Post, Money Magazine, US News and World Report, the Boston Globe, Investment News and Kiplinger’s Personal Finance.  Cheryl is also a regular contributor to the Boston Globe’s “Money Makeover” series and she has been interviewed on Boston’s NPR station.

Before founding Woodside Wealth Management, Cheryl was a Principal of Forteris Wealth Management and a Shareholder and Principal Advisor with Family Financial Architects.

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Matthew Costa, CFP®

Financial Advisor

Matt is a Cum Laude graduate of Boston University's Questrom School of Business. At BU, Matt majored in Business Administration with a concentration in Finance and a minor in Economics. He achieved the CFP® designation in 2018 and has a Certificate in Financial Planning from Bryant University. Matt is also a member of the Financial Planning Association and the National Association of Personal Financial Advisors.

Before joining the firm, Matt worked at Verizon where he worked in Financial Planning & Analysis for the Product Innovation and New Businesses team. This team was responsible for developing Verizon's emerging non-core businesses, such as the Internet of Things and telematics.

Matt supports Cheryl with client-related activities and manages the back office operations of the firm. Additionally, Matt will be leading Woodside's initiative to increase involvement with its Gen Y clients.

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Kevin Henderson


Kevin is an intern with Woodside Wealth. He is a Senior at Bentley University where he is majoring in Corporate Finance and Accounting, with a focus in financial disciplines. Throughout his studies, he has taken classes such as Advanced Managerial Finance and Capital Markets and Investments. He is the President of Bentley’s Tour Guide Program, a Resident Assistant for upperclassmen and is a member of the Men’s Club Volleyball team. He will graduate in the spring of 2019 and plans to attend graduate school in the future.

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Miriam Miller

Client Services Administrator

Miriam graduated from Bentley University with a Bachelors Degree in Economics and Finance and an Associates degree in Management. Previously, she was employed by Berkshire Mortgage Finance in Boston for 13 years where she worked as the firm's Mortgage Loan Closing Manager and as a Commercial Mortgage Underwriter for Multifamily Projects. Miriam has great attention to detail and a keen interest in the field of personal financial management.

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