Human Resources Department


  • Director of Human Resources - Michelle Vibert
  • Human Resources Coordinator - Caitlin White

Available job opportunities

Due to the COVID-19 pandemic and the small office staff size, employees are not always in the office. The voicemail is being monitored but the quickest way to receive a response is by email.

The office is staffed on Mondays, Wednesdays, and Fridays, but please make an appointment ahead of time by booking one here, or by calling ahead.

Human Resources FAQ

Can I make an appointment?

Yes, please schedule an appointment here. Please note that until further notice all appointments are over the phone and with Kiley Burke unless otherwise noted. She is in the office on Mondays, Wednesdays, and Fridays.

How do I login to my Employee Self Service (ESS) portal account (Current Employees)?

Please contact Kiley Burke by email (see right) to receive login information or to reset password. For the Retirement System Portal, please contact the Retirement Office at 781-721-7127.

How do I enroll in health/dental insurance?

You may enroll in insurance only during Open Enrollment (typically in May each year) or if you have a qualifying event (birth/adoption, marriage, involuntary loss of coverage, etc.) You must sign up within 30 days of your qualifying event. Please contact HR by email or phone to get necessary forms.

How do I get forms from the HR office if Town Hall is closed to the public?

Please contact Kiley Burke. Many forms can be sent and signed electronically. If you cannot complete forms electronically, please book an appointment at the link above or by contacting the HR office.

How do I get a Verification of Employment for a Town of Winchester employee?

Town Department Employees: For a simple verbal verification of employment (VOE) please call 781-721-7157. For a written VOE please fax to Ellen Howard 781-721-7156. This includes DPW, Library, and Recreation dept. employees.

School Department Employees: Please email Nancy Clark, School Department Payroll.

I have questions about Medicare Supplement Plans.

Please contact Ellen Howard, Payroll/Benefits Coordinator at 781-721-7116 or by emailing her.

I have a question about deductions on my paycheck.

Please contact Ellen Howard, Payroll/Benefits Coordinator at 781-721-7116 or by emailing her.

How do I get a copy of my birth certificate? 

That is handled by the Town Clerk's office please contact that department.