Strategic Transitions Defined:

Strategic Transition, Inc. was founded in 2012 by Jeffrey Pepi, who got started in the health insurance industry in 1998. That quickly changed when the Commonwealth of Massachusetts decided to change their health care laws for the first time. So in 1999, Jeff moved into helping family’s become financially sound and for many years that was his main focus, but in 2006 health care reform came to Massachusetts again and the Fair Share Contribution was created. In response to a distinct need in market for sound advice William Fields and Jeffrey Pepi founded Health Plan Solutions LLC (HPS). This consulting company focused on helping small to large companies becoming compliant with health care reform. HPS also helped many individuals enroll in state programs such as Mass Health and Commonwealth Care. In 2011 Jeff decided to move in a different direction and focus on helping individuals and businesses take advantage of all State and Federal programs and focus those savings back into other much needed areas such as retirement planning and income protection.


Strategic Transitions strives to render services of the highest quality to its customers. This is achieved through a team approach, the awareness of its employees that their best efforts are essential and, therefore, appreciated, and the knowledge that ultimately everyone will benefit from the company’s successes. To achieve and sustain the highest standard and quality of services, Strategic Transitions promotes the following basic values:

Maintaining or improving its position in the market sector concerned only through superior quality and service

Sustaining the company’s unique and noteworthy services through an ongoing commitment to training and education

We appreciate every opportunity that we are given to help people with their goals and strive for excellence!