Five Star award winner Gary Dennis, CFBS, CLTC

PROFESSIONAL PROFILE

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Gary Dennis, CFBS, CLTC

Founder, Managing Partner & Financial Advisor

Tower Hill Financial Group, Inc.

197 1st Avenue, Suite 250

Needham, MA 02494

Office: 508-269-7900 (call only)

gary@towerhillfinancial.com
www.towerhillfinancial.com

Professional Approach

Gary is the Founder and Managing Partner of Tower Hill Financial Group. His mission is to help his clients identify and map out their current financial picture and define their future financial goals. Alongside an integrated team of specialists, Gary provides innovative and strategic solutions using internationally recognized investment products and world-class insurance services. Through these efforts, Gary is able to develop and service enduring relationships with his clients across the United States.

Described as gregarious and warm by friends and colleagues, Gary is the first to admit that he thrives on human connection. His innate ability to connect with others has played a huge factor in his success in the financial services world, where he has built a business around the notion of giving — his personal philosophy for life.

Community and social activism remain paramount to Gary’s daily habits and mores. He has served on numerous boards, including Marcus Smart’s YounGameChanger Foundation, The Van Noy Valor Foundation and is currently a Board Member for The Cole Strange Foundation. He has served as a past board member at Newbridge on the Commons (Assisted Living) and the Wayland-Weston Rowing Association.

Gary is a member of the Boston Estate Planning Council (BEPC), and from 2000-2023 has been a member of the Million Dollar Round Table (MDRT), which is a membership of the top 2% of financial professionals in the world. Gary is among the select wealth managers in the Boston area who was named Top Wealth Manager by Five Star Professional in 2022, 2023 and 2026*. He was featured in Boston Magazine, Fortune Magazine, and the Wall Street Journal.

Gary graduated from Roger Williams College, has three children, and resides in the suburbs of Boston.

*This award has been awarded by Five Star Professional on 2/1/2026 for the following period 04/10/2025 - 10/01/2025.

See Accomplishments

This award was issued on 02/01/2026 by Five Star Professional (FSP) for the time period 04/10/2025 through 10/01/2025. Fee paid for use of marketing materials. Self-completed questionnaire was used for rating. This rating is not related to the quality of the investment advice and based solely on the disclosed criteria. 4973 Boston-area wealth managers were considered for the award; 449 (9 % of candidates) were named 2026 Five Star Wealth Managers. The following prior year statistics use this format: YEAR: # Considered, # Winners, % of candidates, Issued Date, Research Period. 2025: 4,671, 528, 11%, 2/1/25, 4/10/24 - 10/31/24; 2024: 4,421, 580, 13%, 2/1/24, 4/10/23 - 10/31/23; 2023: 3,923, 578, 15%, 2/1/23, 5/23/22 - 1/6/23; 2022: 4090, 513, 13%, 2/1/22, 5/24/21 - 11/19/21; 2021: 4069, 480, 12%, 2/1/21, 5/25/20 - 11/30/20; 2020: 3580, 463, 13%, 2/1/20, 4/1/19 - 12/13/19; 2019: 3619, 566, 16%, 1/1/19, 4/18/18 - 11/6/18; 2018: 2819, 532, 19%, 1/1/18, 3/23/17 - 11/10/17; 2017: 2467, 623, 25%, 12/1/16, 3/26/16 - 11/23/16; 2016: 2530, 632, 25%, 12/1/15, 5/18/15 - 11/6/15; 2015: 3542, 801, 23%, 1/1/15, 5/18/14 - 11/6/14; 2014: 1707, 655, 38%, 1/1/14, 5/18/13 - 11/6/13; 2013: 2362, 713, 30%, 1/1/13, 5/18/12 - 11/6/12; 2012: 2591, 454, 18%, 1/1/12, 5/18/11 - 11/6/11.

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Securities, investment advisory, and financial planning services offered through qualified registered representatives of MML Investors Services, LLC, Member SIPC (www.sipc.org). Tower Hill Financial Group, INC is not a subsidiary or affiliate of MML Investors Services, LLC, or its affiliated companies. Supervisory Office: 280 Congress Street Suite 1300 Boston MA 02110. (617) 439-4389. CRN202610-4988860.

Wealth managers do not pay a fee to be considered or placed on the final list of Five Star Wealth Managers. The award is based on 10 objective criteria. Eligibility criteria – required: 1. Credentialed as a registered investment adviser (RIA) or a registered investment adviser representative; 2. Actively licensed as a RIA or as a principal of a registered investment adviser firm for a minimum of 5 years; 3. Favorable regulatory and complaint history review (As defined by FSP, the wealth manager has not; A. Been subject to a regulatory action that resulted in a license being suspended or revoked, or payment of a fine; B. Had more than a total of three settled or pending complaints filed against them and/or a total of five settled, pending, dismissed or denied complaints with any regulatory authority or FSP’s consumer complaint process. Unfavorable feedback may have been discovered through a check of complaints registered with a regulatory authority or complaints registered through FSP’s consumer complaint process; feedback may not be representative of any one client’s experience; C. Individually contributed to a financial settlement of a customer complaint; D. Filed for personal bankruptcy within the past 11 years; E. Been terminated from a financial services firm within the past 11 years; F. Been convicted of a felony); 4. Fulfilled their firm review based on internal standards; 5. Accepting new clients. Evaluation criteria – considered: 6. One-year client retention rate; 7. Five-year client retention rate; 8. Non-institutional discretionary and/or non-discretionary client assets administered; 9. Number of client households served; 10. Education and professional designations. FSP does not evaluate quality of services provided to clients. The award is not indicative of the wealth manager’s future performance. Wealth managers may or may not use discretion in their practice and therefore may not manage their clients’ assets. The inclusion of a wealth manager on the Five Star Wealth Manager list should not be construed as an endorsement of the wealth manager by FSP or this publication. Working with a Five Star Wealth Manager or any wealth manager is no guarantee as to future investment success, nor is there any guarantee that the selected wealth managers will be awarded this accomplishment by FSP in the future. Visit www.fivestarprofessional.com.