Dean Health Plan offers different ways to enroll. We advise working with one of Dean's Medicare Representatives when enrolling to ensure the application is filled out appropriately. Online Easily enroll online today! Online In person Call 1-877-234-0126 to schedule an appointment. In person Phone Call 1-877-234-0126 to enroll over the phone. Phone Paper application Receive a paper application via mail by calling 1-877-234-0126. Paper application Dean Medicare Representatives are available via phone 8 am – 8 pm, weekdays (year-round) and weekends (Oct. 1 – Feb. 14). TTY users should dial 711. Our representatives can also help you understand Medicare, learn about your plan options and answer questions.