Benefits & Insurance

Welcome to the Town of Wellesley Benefits Information Page

Information on coverages offered, how to enroll in the online benefit tool and the effective dates of coverages elected can be found by clicking the icons below. Benefit enrollment via the online enrollment tool can only be done at open enrollment, as a new hire, as a newly benefit eligible employee or as an employee returning from an unpaid leave of absence.  

Please be advised that initial selections and subsequent changes to your benefits can only be made during the first 30 calendar days from your hire date, a qualifying event (birth, death, adoption, marriage, divorce, etc.) or during open enrollment.  Day 1 of the 30 day deadline begins on the date of hire or the qualifying event change. 


You can make changes to your benefits within 30 calendar days of a qualifying event. Click HERE for instructions on what to do and what is needed to enroll.

Insurance OfferingsOnline Enrollment Link and InstructionsCoverage Effective Date
insurance optionsonline enrollmentcalendar

please note

Information regarding benefits and benefit enrollment is sent to the email address the employee has provided for payroll purposes.  Please check your email for any information related to benefit enrollment to include signing up for the first time and possible issues with your enrollment.  Any enrollment issues not addressed during the first 30 days of your employment will result in the inability to enroll in benefits until the next open enrollment period or as a result of a qualifying event.   

If you have any questions on the benefit offerings available for eligible employees, please contact the Town of Wellesley Human Resources Office at (781) 431 - 1019, extension 2244 or by emailing