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Oakland Unified School District

Planning to retire from OUSD

Congratulations on your decision to retire from OUSD!

So what’s next?

There are lots of positive things to look forward to, such as traveling, developing hobbies, reconnecting with old friends and volunteering. Whatever you do, you must remain healthy. That is why maintaining health benefits is crucial. Whether you stay with OUSD or enroll into an outside plan, health should be your number one focus during your retirement. Below you will find some important information that will assist you in your transition from Employee to Retiree.

One of the most important things to remember: You DO NOT have to apply for Medicare when you turn 65 if you are still actively working. You are exempt until you separate and/or retire. Please meet with a Talent Staffing Assistant to discuss this further as lifetime penalties can be imposed. 

Start Preparing as soon as you know you are ready to retire:

  • Contact CalSTRS or CalPERS to discuss your retirement date and confirm your retirement benefits with them (this is not health benefits).
    CalSTRS 800-228-5453
    CalPERS 888-225-7377
  • Register for or view a Medicare 101 Webinar. Whether you’re about to retire or already enrolled in a Medicare health plan, knowing more about your Medicare benefits can give you an advantage. All Oakland Unified School District employees are eligible to enroll in a Medicare health plan designed exclusively for Oakland Unified School District retirees.
  • Contact your supervisor and let them know of your impending date.
  • Submit the Separation Form so the Talent Division is alerted.
  • Review this page and the current retiree rates.
  • Attend our benefits drop-in hours on Thursdays from 3-4pm on Zoom. If that time doesn't work, you can email Benefits and we can set up a time. 

If you will be 65+ at the time of retirement / separation, you need to coordinate with Social Security and Medicare:

  • Contact Social Security at least 3 months prior to your retirement/separation date once you have confirmed your retirement date.
  • Medicare
    • Be sure you have signed up for Medicare Part A before you turn 65. This needs to happen within 3 months of your 65th birthday, regardless of whether you are retiring, or will be applying to use Medicare.
    • You don't have to sign up for Medicare part B until you need health coverage. If you are still covered as an active employee, it's enough to sign up for part A so they have a record of you when you want to apply for Part B.
    • Medicare shouldn't overlap employee coverage. Your requested Medicare effective date should be the first day of the month following your last day of active coverage.
      • For OEA members, if you work the full school year and you are either retiring or laid off, your benefits remain active until August 31st.
      • For Non-OEA members (all other unions), your benefits will end on the last day of your retirement month.
        For example: If you are retiring on June 10th, your benefits will remain active until June 30th (of the same year). 
  • If you have any questions about your last check, vacation and/or sick leave payout, reach out to Payroll.

For Employees with an OUSD District Annuity:

  • Classified Employees contact BeneSys Administrators 877-494-0522 | 925-398-7045
  • Certificated Employee contact 866-376-2307

For Employees with Voya Life Insurance (Employer Paid and/or Supplemental):

  • Contact Benefits if you interested in continuing on the plan.

For all other personal annuity and/or life insurance accounts for which payroll deductions are made:

  • Reach out to those companies directly to find out what is needed to either continue to pay or terminate accounts.
  • Contact Payroll for signatures as needed.

Meeting with a Benefits Representative

You will not automatically be enrolled onto retiree benefits. You must meet with a Benefits Rep to discuss retiree plans and deadlines. Your Benefits Rep will discuss the following:

  • Medicare Eligibility and Timelines
  • Retiree Health Benefit Plans offered and Rates
  • Covering Dependents
  • Retiree Benefit Enrollment Forms
  • COBRA Benefits vs. Retiree Benefits

Please attend our benefits drop-in hours on Thursdays from 3-4pm on Zoom. If that time doesn't work, you can email Benefits and we can set up a time. 


  • you leave the District without enrolling onto benefits, you cannot come back to enroll at a later time.
  • you decide to use an outside insurance provider for medical and only take OUSD dental and/or vision, you cannot come back to enroll onto our medical plans at a later time.
  • you are 65+ and do not have your Medicare in place at the time of retirement and you wish to remain on OUSD benefits, you will need to enroll onto the Early Retiree plan to bridge the gap until your Medicare becomes active. At which time, you will need to bring proof of eligibility to OUSD the month BEFORE your requested effective date to enroll onto a Medicare advantage plan.
  • you enroll onto the OUSD Retiree Health Plans, you are eligible to keep them until you decide to terminate (not withstanding any other issues with eligibility and/or premium payments)
  • you enroll onto OUSD Retiree Health Plans, please DISREGARD the COBRA notice you will receive. COBRA notices are sent to ALL Employees who separate from the District. COBRA, while slightly cheaper, is only for 18 months for most. Please see a Benefits Rep if you require more information.

Contact Us

1011 Union Street, Site 944
Oakland, CA 94607

(510) 879-0202

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Weekly drop-in hours

The Benefits Team holds weekly drop-in hours on Thursdays from 3:30pm-4:30pm on Zoom

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