About Us


Ryan McDermott, Partner

Ryan’s day to day activities involve connecting with business leaders – Founders, CEO’s, Financial Executives, and Human Resource leaders – to create wealth opportunities while solving HR problems with best-in-class Employee Benefits programs. He is the strategic voice in the room – always listening first to fully understand his clients’ needs so that he can more accurately advise on the next steps.

As a technician, Ryan has expertise in traditional employee benefits programs – Health & Welfare, Retirement Plans, Voluntary Benefits and Supplemental Benefits Programs. He also has a Financial planning background which uniquely positions him to help everyone from the C-Suite down to the Entry level employee develop wealth strategies around the benefits that they’re providing for their employees.

Ryan is currently the President of the Dedham Square Circle – an organization focused on the Small Businesses that make up Dedham’s Downtown District. The organizations’ goal is to increase economic prosperity by promoting Dedham Square’s Small Businesses along with its rich history and culture while also working to enhance the Square’s physical environment to benefit the entire community.

He is also the immediate Past President and Chairman of the Boston Irish Business Association (BIBA) and remains on the organization’s Board of Directors. In his work with BIBA, he’s had the opportunity to travel as a delegate to Ireland on trade missions with the goal of building and strengthening trade relationships and diplomacy between Massachusetts, Ireland and Northern Ireland. He was honored by the Irish Echo NewsPaper – the largest and most widely-read Irish-American weekly in the US – with a 40 Under 40 Award in 2012 and with a Small Business Big Impact Award in 2019.

Ryan has served on the Board of Directors of the National Association of Insurance and Financial Advisors (NAIFA) regularly participating in State and National advocacy work on behalf of Families and Small Businesses in Massachusetts.

Ryan resides in Dedham, MA with his wife Kara and their three children.

Josh O’Gara, Partner

The financial services industry covers a wide spectrum of subject matter and the biggest asset that Josh brings to his clients is his depth of experience and knowledge in a variety of industry segments. Combined with his deep desire to help his clients, regardless of their financial status, and seeing an increasing financial burden being placed on everyday working Americans, Josh founded O’Gara Financial Group in 2017 with the primary goal being to serve small businesses and their employees.

Josh began his career in financial services in 2006 as a Financial Representative with Northwestern Mutual. In this role, he gained experience working with both individuals and businesses to help them with their insurance planning needs

In 2007 he moved to First American Insurance, an insurance brokerage firm, where he gained extensive expertise with individual life insurance, disability insurance, long term care insurance and annuities, typically working on well over 300 cases per year. Josh became an expert in being an “advisor to advisors”, helping to design effective insurance solutions for clients across the country. He wrote extensively on the subject and was published in industry magazines such as “Broker’s World”, “Advisor Today” and “Insurance News”.

During his time with First American, he also worked hard to further his financial education. His “always be learning” attitude led him to earn the Chartered Life Underwriter and Chartered Financial Consultant designations from the American College as well as the Certified Financial Planner designation from the CFP Board.

In 2015 Josh was offered an opportunity to work for one of the country’s largest insurance companies to help them build out their distribution amongst independent agents. While working in their Boston office, Josh was involved in complex business and estate planning cases and was one of the top Brokerage Directors in the country for Long Term Care insurance.

After being back working with a large insurance company, in 2016 Josh decided to pursue an opportunity to develop his own agency with Colonial Life. Josh’s significant background working with individuals proved invaluable to working in the benefits market and taking an individualized, tailored approach to every client. By taking a client centered approach, other opportunities to help businesses arose outside of worksite benefits. Josh founded OFG to take a more holistic view and change the way employers and their employees perceive their benefit plans.

Josh grew up in Dorchester, and his wife Julie in Watertown, so they have strong connections in the Boston area. They currently live in Woburn with their son Declan and Boston Terrier-Frenchie mix, Frankie. For rest and fun, they usually escape north to the lakes of New Hampshire and can be found doing anything that gets them outdoors.


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