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

Founder, CEO

Bill is the founder of Stateline Senior Services’. Bill has a wealth of experience having served over 5,000 senior citizens in Connecticut and Western Massachusetts over the past 30 years. Bill works primarily with our investment clients. He handles all financial matters for annuities and investments as well as estate preservation, long-term care and life insurance.

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.

Wendi Jamison

Wendi Jamison

Client Services Manager

Wendi has worked for Stateline Senior Services since February of 2011. She oversees all aspects of client services for both the financial and the insurance components of our business.

Kate McCloskey

Kate McCloskey

Senior Advisor/Client Services

Kate has worked for Stateline Senior Services since April of 2015. She has gotten her insurance license and handles that part of our business. She is involved in all areas of Medicare sales and service.

Christine Olmstead

Christine Olmstead

Client Services

Christine has worked for Stateline Senior Services since June of 2016. She is handling all aspects of client services for the insurance side of our business. She also performs various tasks and duties throughout the office.