Who We Are

Gerald J Kennedy
Co-Founder and CEO
Gerry is the Chief Executive Officer of OSM, Inc. and is one of the two founding shareholders of the Company. Gerry is also the founder of Charles River Insurance Brokerage of Framingham, Massachusetts. In 1998 he left the insurance underwriting ranks and founded CRIB, a New England based premier insurance organization whereby he was instrumental in the company’s growth.
Prior to CRIB, Gerry worked for several insurance carriers including Norfolk & Dedham, Kemper Insurance, Travelers and USF&G in the national brokerage/large account arenas and held various underwriting and management roles as well. Gerry graduated from St Anselm College of Manchester, New Hampshire with a BA in Business in 1988.
Gerry is the proud father of Captain Brian Kennedy, a USAF pilot and Meghan his wonderful daughter a recent graduate from Penn State University. Gerry is passionate about helping people help themselves though business and life in general.

Rogan C Dwyer
Co-Founder and President
Rogan is the President of OSM Inc. and is one of the two founding shareholders of the Company where he oversees operations, marketing, strategy and product development. Rogan is also CEO of Waters Insurance Network, LLC. which gives OSM access to the insurance industry platform.
Prior to joining OSM, Rogan has been President of Global Asset Protection, Inc. an independent insurance agency focused on US business overseas exposures which he founded in 2000. In 2010 Rogan was engaged in setting up and serving as CEO of a Bermuda licensed insurance company providing extension risk for the Life Settlement industry, a role continued until 2013 when he resumed a more active consultancy role in the US providing services to various market sectors including energy, security and cyber.
In meeting Gerry Kennedy in 2017, Rogan and Gerry discovered their shared interest in improving insurance outcomes and this led them to the ground-breaking partnership they have created at Observatory.
In 2000, Rogan immigrated from the United Kingdom where he had spent twenty-three years at Lloyd's of London, culminating in a role as Named Underwriter of Syndicate 323 specializing in non-marine business.