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About Us

Waypoint Financial Planning LLC is a Registered Investment Advisor in the Commonwealth of Massachusetts, serving clients in the Boston MetroWest area and throughout greater Boston.

As a Registered Investment Advisor, Waypoint is required by law to put client interests first — we have a fiduciary duty to our clients.  We are independent, fee-only and do not sell or receive commission on financial products.

We specialize in Retirement Planning and provide comprehensive financial planning services in the model of the Certified Financial Planner Board of Standards, Inc. Practice Standard for Personal Financial Planning.

We provide Investment Management for clients, with no minimum of assets under management but a nominal minimum annual fee.

To discuss your needs or to arrange a low-key, free initial meeting, please contact us.


About Alan Dossett

R. Alan Dossett is President and owner of Waypoint Financial Planning LLC, and is a Certified Financial Planner™.

Alan graduated from Cornell University in 1983 with a BS Engineering, majoring in Computer Science.  He worked as a software engineer and Information Technology manager for computer and software companies in the Boston area until taking a position with Fidelity Investments in 1994 in the IT division of the company.  He gained an in-depth understanding of the mutual fund industry at Fidelity, and began to pursue financial planning as a career in 2007 by enrolling in Boston University’s Center for Professional Education, receiving the Certificate of Financial Planning in the spring of 2010.

Alan left Fidelity and founded Waypoint Financial Planning in the spring of 2011.  He earned the Chartered Retirement Planning Counselor CRPC®  designation from the College for Financial Planning.

Alan is a member of the National Association of Personal Financial Advisors (NAPFA), serving as Treasurer of the Boston chapter.  NAPFA is a professional organization of Certified Financial Planners™.

Alan has spoken at Clark University in Worcester, MA on the subject of financial literacy, and participated in the Kiplinger’s “Jump Start Retirement” event, answering questions in a live chat.  Alan has been quoted in stories for the Boston Globe, fidelity.com web site, and Investment News.

Alan is a registered Investment Advisor Representative, CRD #5975284, holding the Series-65 license after passing the Uniform Investment Adviser Law exam in October 2011.


Alan lives in Milford, Massachusetts with his wife, son, and two very happy dogs.  Alan is an active volunteer  in his church, having served on leadership boards and traveling with a work group each summer to western Maine to renovate housing for low-income families — work that offers great perspective throughout the whole year.  In his spare time, Alan roasts coffee for family and friends, with one friend declaring, “It’s the best coffee I’ve ever had!”  Alan’s latest hobby is home brewing beer.  Alan also enjoys landscape photography; some of the photos on this site were taken by him in New Hampshire, Nantucket, and Mount Desert Island.

To discuss your needs or to arrange a low-key, free initial meeting, please contact us.

Please see important disclosures and information in our Form ADV Part 2.

About Jackie de Boer

Jackie is Executive Assistant at Waypoint Financial Planning LLC.  She assists with scheduling, client communication and practice management.  Originally from England, Jackie has lived in Japan, and various parts of the US.


Graphic Design by C. VanCott Arts

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