Independent guidance for Medicare, individual and family health insurance, small business group health insurance, and life insurance planning. Clear advice. Personalized service. Long-term support.
Randy Gregory is the owner of Core Benefits Gregory Group, an independent insurance agency serving clients in Massachusetts. He specializes in Medicare planning, individual and family health insurance, small business group health insurance, and life insurance planning.
Randy has spent nearly 20 years helping individuals, families, and businesses make informed insurance decisions. He began his career with New York Life, where he spent more than 14 years helping clients with life insurance, financial planning, retirement strategies, and health insurance solutions.
Today, as an independent broker, Randy is able to represent multiple insurance companies rather than just one. This allows him to recommend coverage based on what best fits each client's doctors, prescriptions, budget, and individual needs—not the interests of any single carrier.
Randy's approach is educational and straightforward. He believes clients make the best decisions when they fully understand their options, so he takes the time to explain everything in plain language without pressure or sales tactics.
One of the experiences that shaped both Randy's life and career was serving as the primary caregiver for his late wife, Nicole, after a spinal cord injury left her paralyzed.
Navigating Medicare, Medicaid, doctors, hospitals, rehabilitation, prescriptions, and long-term care gave Randy firsthand insight into how overwhelming the healthcare system can be. It also showed him how valuable knowledgeable guidance can be when people are facing difficult decisions.
After Nicole passed away in 2017, Randy decided to focus his career on helping others navigate Medicare and health insurance. He expanded his Medicare expertise working with Humana, assisting clients across the country, before becoming a Medicare Field Representative for Aetna Medicare in Massachusetts.
While Randy's primary focus today is Medicare and health insurance, he also helps individuals, families, and business owners with life insurance for family protection, income replacement, final expenses, and business planning needs.
“My goal is simple: to provide honest advice, personalized guidance, and become a trusted resource my clients can rely on for years to come.” — Randy Gregory
Core Benefits Gregory Group helps individuals, families, retirees, and small businesses navigate today's complex insurance landscape. I compare multiple carriers, provide objective recommendations, and meet with clients in person, virtually, or by phone. My support continues long after enrollment with questions, annual reviews, and guidance as your needs change.
Helping individuals confidently transition into Medicare by explaining Medicare Advantage, Medicare Supplement (Medigap), and Part D prescription drug plan options.
BenefitsIndividuals turning 65, retirees, people leaving employer coverage, and current Medicare beneficiaries reviewing their coverage.
Contact Randy →Helping individuals, families, self-employed professionals, and early retirees find affordable health coverage through private plans or the Health Insurance Marketplace.
BenefitsIndividuals, families, self-employed professionals, early retirees, and anyone losing employer-sponsored insurance.
Helping small businesses compare and implement group health insurance options that balance quality coverage with cost.
BenefitsSmall businesses, startups, growing companies, and employers looking to attract and retain quality employees.
Contact Randy →Helping individuals, families, and business owners protect the people and priorities that matter most through personalized life insurance strategies.
Planning OptionsYoung families, homeowners, business owners, professionals, and individuals planning for retirement or estate preservation.
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View Reviews ↗It is wise to begin reviewing Medicare options several months before turning 65 or before leaving employer-sponsored coverage. Early planning can help you understand enrollment periods and avoid gaps in coverage.
Yes. Core Benefits Gregory Group helps small businesses compare group health insurance and employee benefit options, support employee enrollments, and review coverage at renewal.
The right Medicare option depends on your doctors, prescriptions, preferred pharmacies, budget, travel needs, and comfort with provider networks. Randy reviews those factors before making recommendations.
Costs can vary depending on the type of insurance and service. Contact Randy directly to discuss your situation and understand any applicable costs before moving forward.
Yes. Randy can review existing Medicare coverage, compare current options, and help you understand whether your plan still fits your doctors, prescriptions, healthcare needs, and budget.
An independent broker can represent multiple insurance carriers instead of a single company. This allows recommendations to be based on the client's needs rather than the products of one carrier.
Let's have a conversation about your healthcare, insurance, and financial protection goals and find solutions that fit your needs.