Staff

Executive Director

Bill Benson joined Boots2Roots in 2019 after a successful stint as the owner/operator of a small manufacturing business in Maine. Prior to owning his business and before moving to Maine in 2014, Bill spent 24 years on active duty with the United States Army. Bill is a combat veteran who served over 42 months deployed to Iraq and Afghanistan. When not deployed, Bill enjoyed tours of duty in places like Texas, California, Germany, Colorado, Kansas, Georgia and Tennessee.

When it came time to transition, Bill, his wife Tara, and their three children chose to settle in Maine because, out of all the places they lived, Maine felt most like home. Bill joined Boots2Roots because of the opportunity to use his own experiences as a veteran and business owner to assist other transitioning service members in finding meaningful work and put down roots in Maine.

Program Director

Randy Bell joins Boots2Roots after a 23 year career in the United States Navy. Randy retired from active duty in 2023 as a Command Master Chief, the most senior enlisted rank in the Navy. He most recently completed a tour on the USS AMERICA (LHA 6) stationed in Japan, before moving to Maine with his family.

Randy brings his experience in developing military talent to lead Boots2Roots’ Transition to Work Program. As Program Director, Randy is responsible for ensuring best outcomes for military members transitioning to the civilian workforce in Maine, and in growing the program to meet the increasing workforce needs of Maine employers.

Military Transition Specialist

Ron is a 30+ year retiree of the US Air Force with time split between Active Duty and Reserve service as an F16 Pilot and Operations Officer.  He most recently completed tours at NORAD before moving to Maine in 2021 with his family.

Ron has a passion for helping military members find work with purpose and understands the value military talent brings to Maine’s workforce. As Boots2Roots’ Military Transition Specialist, Ron is responsible for assisting our servicemembers and spouses navigate their journey to meaningful work in Maine. If you are a transitioning military member looking for information about putting down roots in Maine, or a Maine business looking to hire military talent, he is ready for you to reach out.

Military Transition Specialist

Disa is a 20-year military spouse who returned to Maine with her family after her husband retired from the Air Force in 2021. During their military career Disa and her family lived in Alaska, Virginia, Delaware, Nevada, and Illinois, but were eager to return to Maine as soon as they could.

Disa joined Boots2Roots in 2023 because she is passionate about helping servicemembers and military spouses find work in Maine. She brings her own civilian work and transition experiences to the team, and is an important addition to Boots2Roots. As a Military Transition Specialist, Disa is responsible for assisting military members and their families in their transition to Maine by helping them translate their unique military experiences into skills that hiring managers can understand, and by connecting them with Maine employers.