OUR TEAM
Who We AreA Heritage of Trust and Understanding
At Holt Financial, our practice pays homage to a family history rooted in hard work, teamwork, and integrity. We focus on serving high-earning individuals, specifically medical professionals and equity-compensated directors, who value a thorough and communicative approach to wealth management.
We understand that before we can solve complex financial issues, we must first connect with you to understand the 'why' behind your objectives. Our team strives to be a reliable resource, guiding you through life's decisions to help position you and your family for long-term success.
Thomas Holt, CFP®
Wealth Advisor
As a CERTIFIED FINANCIAL PLANNER™ professional, I believe that great financial advice starts with comprehensive planning—not product placement. My approach is rooted in the idea of diagnosis before prescription, much like the medical field, ensuring that recommendations are made only after fully understanding each client’s unique goals, risks, and circumstances. Since entering the financial services industry in 2012, I have focused on delivering thoughtful, objective guidance through a team-based approach, frequently collaborating with specialists across tax, estate, insurance, and investment disciplines to help provide well-rounded solutions. I live in Charlestown, Massachusetts with my wife, our one-year-old son, and our golden retriever. I value building long-term relationships that align financial decisions with what matters most in life.
Bobby McCloskey
Paraplanner
In his Paraplanner role, Bobby supports individuals, families, and business owners by assisting with insurance and financial protection discussions. Working alongside an experienced team of financial professionals, he helps facilitate the planning process and provides support throughout the client experience.
Bobby holds a bachelor’s degree in finance from Lake Forest College. He has (~9 Months) of experience in the financial planning industry.
Bobby lives in Marblehead, MA. He enjoys boating, skiing, travelling, and playing hockey and golf.
*Licensed to administer life and health insurance in MA.
Strategic Resources
Abigale Shields, CEPA®
Vice President of Advice & Strategy
Abigale Shields began her career with Baystate Financial in 2011 as a Sales Support Consultant on the Sales Desk and transitioned to the Financial Planning Department in late 2012. As Baystate’s Director of Financial Planning, Abigale is now responsible for the development and growth of the firm’s financial planning department as well as the continuing education of existing Baystate Financial Planners. Abigale is an advocate of holistic planning, which takes into account the client’s overall goals and current situation in order to provide the best possible advice and guidance for their future.
In addition to leading her team, Abigale manages the firm’s financial planning and Personal Financial View software and trains financial advisors to utilize these for both client aggregation and planning projections. She facilitates training for existing advisors to become approved Financial Planners and regularly audits and approves financial plans for advisors to deliver to their clients.
Abigale Shields graduated from Wheaton College in 2011 with a bachelor’s degree in Economics and holds her Series 6, 63 & 7 licenses.
Alan Roycroft
Senior Vice President of Investments
As the Head of the Investment Department, Alan R. Roycroft is responsible for helping advisors and sales managers meet client investment goals and objectives.
Before joining Baystate Financial, Alan was a Director of National Sales for the MetLife Broker-Dealer Group where he specialized in helping advisors develop the techniques and skills to become the best in the business and arm them with a wide array of business-building solutions and strategies to solve specific client problems.
Alan R. Roycroft has over 20 years of professional sales and management experience that began in asset management and has culminated for the last 18 years with a variety of sales and marketing roles in the development and management of the Broker-Dealer at MetLife.
Alan holds a Bachelor of Art degree from Salve Regina University and holds his Series 7 and 24 licenses. He was born and raised in the Boston area, and during his free time enjoys skiing, golfing and following the financial markets. Alan lives in Westwood with his wife Maureen and his three children, Sarah, Katie and Jack.
Herbert Daroff, J.D.*, CFP®, AEP®
Director of Estate and Business Planning
Herbert K. Daroff has been with Baystate Financial since 1996. He sees himself as a professional problem solver, educated as an engineer and attorney, and practicing as a Certified Financial Planner™ professional. Herb earned a B.S. in Commerce & Engineering from Drexel University in 1975 as well as a J.D.* from Temple University School of Law in 1979, where he was the Evening Division Class President.
Herb’s primary expertise is multi-generational tax planning and multi-generational creditor protection. He is a very active volunteer in his community and in financial services,. His activities in these areas include:
Leadership as past President of the Greater Boston Chapter of the International Association for Financial Planning (IAFP, now FPA, Financial Planning Association);
Leadership as past President of the Boston Society of Financial Services Professionals;
Involvement as a former member of two national CFP® Board committees, Board of Practice Standards and Board of Professional Review;
Involvement as a former member of the national IAFP Ethics Committee;
andTime spent as member of the adjunct faculty at Bentley University in Waltham, MA
Herbert K. Daroff’s creativity, experience, and resourcefulness enable him to work very well with the public and their professional advisory team in order to implement solutions responsive to each client’s financial objectives.
*Not practicing on behalf of MML Investors Services, LLC or its affiliates.
Bobby Piatelli
Director- Life Products
Robert (Bob) Piatelli is the Director of Life Insurance Sales and Marketing. He began his career at Baystate Financial in 1975 before leaving to work at New England Financial in Product Design and Development. After a few years Bob returned to Baystate Financial where he is currently the Life Insurance Specialist with the Advanced Markets team.
With 38 years of experience in the life insurance industry he focuses on the sale and conservation of life insurance. Bob works closely with advisors to help them with case design that will assist them in finding the best solutions for their clients’ needs.
Bob is on the Board of Friends of Special Olympics where he also volunteers his time as a flag football coach.
Bob is married and the proud father of three grown sons.
Eli Hopkins, CFP®, CEPA®
Financial Planning Director
Specialist Eli is a CERTIFIED FINANCIAL PLANNER™ dedicated to helping clients achieve their financial goals through comprehensive, personalized planning. He takes an educational approach, guiding clients to better understand their current financial situation while providing clear, actionable recommendations to build a practical roadmap for the future. By focusing on clarity and empowerment, he helps clients make confident decisions and stay on track toward their desired outcome. In addition to the work Eli does with clients on a daily basis, Eli helps run and grow our financial planning department. He serves as the financial planning technical lead, guiding advanced planning strategy and solutions. In addition to influencing advisor engagement and uncovering new opportunities through impactful financial planning presentations, education, and joint work. Outside of work, Eli enjoys golfing, spending time with family and friends, and relaxing down the Cape.
Michael Oliveira
Brokerage Director
As Brokerage Director & Disability Income Specialist , Michael plays a key leadership and support role within the brokerage distribution side of the business, focusing on helping independent brokers and financial professionals succeed with products and services at Baystate. In addition to his responsibilities as Brokerage Director, Michael serves as Baystate’s Disability Income Specialist, partnering with advisors and clients to design and implement income protection strategies tailored to individual needs.
Before joining Baystate Financial, Michael Prior to being promoted to Brokerage Director in early 2025, Michael led the Sales Support team for three years, working closely with advisors to support case development, product strategy, and day-to-day execution.
Michael has 5 years of experience in the industry that all started at Baystate.
Michael holds a bachelor’s degree from Roger Williams University and maintains his Series 7 registration, along with state Life and Health insurance licenses. Michael was born and raised in Waterville, Maine, and enjoys traveling, golfing, and spending time with family and friends in his free time. He currently resides in Charlestown, Massachusetts, with his fiancée, Morgan.