Our Team : Dickinson Wealth Strategies | Salem, MA

Our Team


Dennis A. Dickinson Jr.

Dennis A. Dickinson Jr. is the President and Founder of Dickinson Wealth Strategies, LLC. Dennis has helped his clients in different aspects of business and estate planning, risk management, comprehensive financial planning, investment advisory and wealth management services to business owners and families since 2002.

Dennis is a Member of The Nautilus Group® which is a service of New York Life Insurance Company, as well as an Investment Advisor Representative with Eagle Strategies, LLC, a Registered Investment Advisor, and a Registered Representative with NYLIFE Securities, LLC.

He is a graduate of Salem State University and has continued his studies through the American College. Dennis is also a life and qualifying member of the Million Dollar Round Table as well as earning Top of the Table honors in 2018. MDRT is widely recognized as the standard of excellence in the financial services industry.

When he is away from the office, Dennis enjoys playing golf, traveling, as well as philanthropic work. Dennis and his wife Aleksandra reside in Marblehead, Massachusetts. They have two boys who are avid hockey players and swimmers as well as their family dog named Izzy, who will do anything to for a treat and a family walk to the beach.

Personal Side

Dennis is a Berkshire County “native” who moved to the North Shore area over 20 years ago. He fell in love with the area, and if asked today, he would vow he will never leave the little town of Marblehead where he and his wife settled nearly a decade ago. Today, life’s biggest joy is the time spent with family and friends. Dennis is a passionate golfer and his love for the sport is definitely contagious, as the family golf club collection seems to be growing rapidly. But golf isn’t the only sport Dennis is passing onto the next generation. His younger son, Brody caught the hockey bug his father once had himself, and at 7 years old being an NHL goalie is his dream! Although the entire family adores watching the little man play on the ice, his older brother Cameron found great passion in skiing in the winters and beach hopping the North Shore coastline in the summers. It may seem tricky to keep life balanced between family, work, everyone’s hobbies and passions, but the time spent together is ever so priceless to all.

Professional Side


Aleksandra Dickinson

Director of operations and business development

Over the last 15 years, Aleksandra has built a career grounded in operational acumen and a deep commitment to client and community engagement; which have been seminal to the founding and growth of Dickinson Wealth Strategies, LLC. Since the company's inception, Aleksandra has focused her time toward marketing, corporate development and ensuring the highest levels of engagement with their growing portfolio of clients.

In addition to her role at DWS and being a mother to two young sons, Aleksandra is also the president of the non-profit (501c3) the Understanding Cam Foundation, which Dennis and Ally launched in 2013. As passionate advocates for their autistic son, Cameron and many others in their local community, their foundation has raised and donated over more than a quarter of $1 million to support local school and community programs for individuals and families effected by autism.

Outside of her professional and philanthropic endeavors, Ally enjoys boating, interior design and cooking for her family and friends. She and Dennis live in Marblehead with their two sons Cameron and Brody and their dog Izzy.


Grace Cosco

Financial Services Professional

Grace is responsible for providing financial strategies and relationship management for Dickinson Wealth Strategies LLC clients. As a financial professional with expertise in customer service and business development her focus is assisting individuals, families and business owners in the review, development and activation of their financial strategies. Her commitment to operational excellence and client experience ensures that Dickinson Wealth Strategies clients will achieve their goals today and be their partner well into the future.

Prior to joining Dickinson Wealth Strategies, Grace honed her skills providing a truly exceptional customer experience working for Mercedes-Benz. Grace is a Northshore native that lives in Topsfield with her family and dog Gino.