About Stateline Senior Services

Stateline Senior Services was founded by Bill McCloskey having a wealth of experience serving over 5,000 senior citizens in Connecticut and Western Massachusetts over the past 30 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 McCloskey

Bill McCloskey

President & Owner

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 Akey

Mickey Akey

Client Services

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.

Michelle Casciano

Michelle Casciano

Office Manager

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.

Beth Ludwig

Beth Ludwig

Senior Advisor

Beth studied at Manchester Community College. She has 25 years of experience in the insurance industry with a focus on medical and fraud management. As a Senior agent at Stateline, she brings a wealth of knowledge to the Stateline client base.
Beth is the proud mother of two great children. During her time away from the office, she is an avid cyclist, runner, and hiker.

Billy McCloskey Jr.

Billy McCloskey Jr.

Client Services

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 McCloskey

Kate McCloskey

Senior Advisor

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.

Jeff Moser

Jeff Moser

Senior Advisor

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 Moser

Sam Moser

Senior Advisor & Client Services

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 Olmstead

Christine Olmstead

Senior Advisor

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.