Stateline Senior Services was founded by Bill McCloskey having a wealth of experience serving over 10,000 senior citizens in Connecticut over the past 35+ years.
Expertise in helping his clients with the Three Pillars of Retirement Planning:
- Protect their wealth and ensure that it lasts.
- Preserve their assets against the risks of retirement, such as stock market and long term care risks.
- Distribute the highest income with the least amount of taxation.
Bill's dedication to the senior community is evident in his 30 years of experience. He has undergone the completion of a 22 part program of study in financial, physical, emotional, and personal issues of aging. This continuing education helps Bill provide relevant and current advice to clients.
Bill graduated from Eastern Connecticut State University with a bachelor degree of science in economics. He lives with his wife Wendy and has four children, Kate, Elizabeth, Billy and Garrett. Bill enjoys spending time with his family and volunteering for the Macie Grace Foundation.
Meet Our Team
We are a team of dedicated professionals, ready to do what ever it takes to meet your insurance needs for the retired and soon to retire
Bill is the founder of Stateline Senior Services. He has a wealth of experience having served over 10,000 senior citizens in Connecticut over the past 35 years. Bill works primarily with our investment clients, handling all financial matters for annuities and investments as well as estate preservation, long-term care, and life insurance.
Bill has four children and one grandchild. He enjoys traveling, snowmobiling, and Misquamicut Beach when he’s away from the office.
Mickey graduated from Ashford University in 2017 with a degree in Human Resources Management. She has over 30 years experience in customer service, office administration and management. She enjoys creating a positive environment for Stateline clients and strives to bring the best in service while assisting them.
Mickey is married to her husband Shawn and has one son. When away from the office, she is active with a local Fife and Drum Corps playing the fife, traveling, Renaissance fairs, and antiquing.
Matt joins the Stateline Team as a Broker with over 18 years in the insurance industry. Recognizing that insurance provides a meaningful solution to financial problems that many clients and families face, Matt enjoys finding creative ways to assist clients in meeting their long-term goals. Matt specializes in Life Insurance Planning, Long-Term Care Planning and Business Planning.
When he’s not at work, Matt enjoys spending time with his beautiful wife, Lauren, and their two sons Trent and Chase. Matt also coaches boys soccer and basketball in Somers.
Michelle has worked at Stateline Senior Services since January of 2006. She handles all financial applications, marketing, licensing, planning, and oversees the operation of the agency day to day. Michelle lives in Somers with her husband Tony and has three children and two grandchildren. She enjoys spending time with the kids, cooking, traveling, and the beach.
Billy McCloskey Jr.
Billy has worked at Stateline Senior Services since April of 2018. Billy is finishing his business degree at Springfield Technical Community College where he’s also played basketball for two years. Billy is eager to help the business grow and help senior citizens with their insurance and financial needs. In his spare time, he enjoys sports, fitness, and spending time with his family and friends.
Kate earned her bachelor’s degree from Charter Oak State College. She’s been working at Stateline Senior Services for the last four years. She is one of our licensed Senior Medicare agent and assists with client services.
When Kate isn‘t working, she enjoys spending time with her son Mason. Teaching people of all ages is something she’s very passionate about and brings the outlook and compassion of an educator into her work at Stateline.
Jimmy joins the Stateline team as a Senior Advisor with over 8 years of experience. As a graduate from Eastern Connecticut State University, Jimmy has his series 6, 63, and Life and Health securities licenses.
Jimmy loves meeting new people and having a true impact on their lives through innovative insurance solutions. He specializes in Medicare Planning, Life Insurance Planning, Extended Care Planning, and Business Planning while helping clients maintain or achieve the lifestyle, they’ve worked so hard to have.
When Jimmy is out of the oﬃce, he spends his time traveling with his lovely wife, MacKenzie, their daughter, Ruby, and their dog, Waﬄes. Jimmy is an avid golfer, works on staying fit, and is an advocate for spontaneous dance parties with his family and friends.
Jeff is a Navy Veteran who upon returning from service worked for Hallmark Cards, Inc. for 33 years before retiring from his Purchasing Manager role in 2014. He‘s an active member of the Somers Lions Club, serving as President for 7 of the 15 years he’s been involved.
In his spare time, Jeff enjoys traveling and hiking with his wife Barbara as well as golfing and woodworking.
Sam is a recent graduate of Bryant University where he studied Actuarial Mathematics and Finance. He is currently starting his first year at Stateline Senior Services where he assists in client services as well as being one of our licensed Medicare agents.
During his free time, Sam can be found spending time with his friends, watching his favorite sports teams and staying active.
Christine has worked for Stateline Senior Services since 2016. This year, she’s earned her State of CT Producers license and has joined our team of Medicare Agents.
When Christine isn‘t working, she’s practicing and teaching yoga or enjoying free time with her husband and family.
Kristina has worked for Stateline Senior Services since January of 2019. She is part of the client service team and enjoys assisting clients.
She is currently in school pursuing a degree in business. When she is not at work, Kristina is spending time with her three children. She likes to travel, hike and watch her kids play in sporting events.