2019 Annual Enrollment

The Annual Enrollment Period for 2019 benefits is: October 24 through November 7, 2018

To enroll, click here: Enroll/View/Change Elections at Your Benefits Resources (YBR).

Your benefits,your way.  

Annual Enrollment is your annual opportunity to compare and enroll in medical and other benefits offered by Sears Holdings Corporation (SHC). Before you begin, please view the SHC Annual Enrollment Video.

Important Notes:  

Take action! Don’t Lose Your Coverage! 

All benefits-eligible associates must actively enroll in the following plans during Annual Enrollment (if they wish to continue coverage next year - 2019):*

• Medical and prescription drug coverage
• Dental coverage
• Vision coverage
• Flexible Spending Account (FSA) or Health Savings Account (HSA) contributions

In addition, all associates must “refresh” their spouse surcharge and tobacco credit elections. None of these elections will carry over from 2018. Although optional life insurance coverage automatically rolls over into 2019, be sure to closely review this coverage as your options and prices may have changed.

* This includes all benefits-eligible associates in the continental U.S., Puerto Rico, Guam, and the U.S. Virgin Islands. Due to state law, associates in Hawaii who do not currently have coverage will default into coverage.

Before You Enroll:

  • Read the 2019 SHC Associates Annual Enrollment Guide: English/Spanish and consider your options for medical and prescription drug coverage.

  • Confirm or update your home address, email address and phone number on MyHR and register your personal email address on YBR.  If you choose to go paperless, you won’t miss out on important benefits messages. Once you’re on the YBR website, go to Your Profile in the upper right and choose the link for Manage Communications.  
  • Go to YBR beginning October 24 to check out the enhancements made available during Annual Enrollment and utilize the various tools and resources to help you make your enrollment decisions.

During Enrollment:

  • Review your options and choose coverage on YBR. You can make changes up until Annual Enrollment closes on November 7.
  • Take a closer look at all your available benefits for 2019. Specifically consider increasing your pre-tax contributions to your Health Savings Account (HSA) if you elect to enroll in the Basic Plan. 
  • Use the various tools and resources listed in the 2019 SHC Associates Annual Enrollment Guide: English\Spanish. SHC remains committed to helping you select the right medical coverage for your situation. That's why helpful tools and resources are made available on YBR to help you make your enrollment decisions. Decide what is right for you and your family.
  • It's a perfect time to take a closer look at your SHC Savings Plan. The SHC Savings Plan is an easy way to save for retirement with pre-tax or post-tax savings and automatic payroll deductions.
  • Update your life insurance beneficiaries. If you have not done so already, you must designate beneficiaries for your life insurance and 401(k) Savings Plan.  You must add your beneficiary designations for life insurance even if you only have company paid life insurance. 

After Enrollment:

  • Make sure to review and print a copy of your Confirmation of Benefits statement to verify your elections. You will  receive a confirmation email and a Confirmation of Benefits statement (PDF) in your Secure Participant Mailbox on YBR within two business days of enrollment. 
  • Make sure your Confirmation of Benefits statement accurately reflects the elections you made during Annual Enrollment. Should you notice an error in elections, please contact the Sears Holdings Benefits Center at 1.888.88sears (1.888.887.3277) and choose option 1 for health and financial benefits, 7 a.m. to 7 p.m. Central time.

Important Tip:

  • Single Sign-On. You can log in to YBR make your enrollment elections by simply entering your SHC Enterprise ID and password! 


  • Go to YBR to access the following tools beginning October 24:
    • Provider Direct - Search for a provider based on factors, like distance, specialty, and language, that are important to you.
    • Medical Expense Estimator - Get help determining what your total out-of-pocket costs will be under each plan for the year, based on estimated usage, services, and deductions.  
    • Health Plan Comparison Chart - See side-by-side comparisons of your SHC Medical plan coverage levels.
    • New Benefits App (Upoint Mobile HR) - Get access to health plan coverage details, ProviderDirect search, spending account balances, 401(k) Savings Plan balances and more. Use your Benefit Site User ID and Password to access your personal information. Biometric authentication (Face ID/Touch ID) is also available.


  • 2019 SHC Associates Annual Enrollment Guide: English/Spanish

  • 2019 Annual Enrollment: FAQs

  • SHC Annual Enrollment Video

  • ConsumerMedical: FAQs

  • Additional Resources: 

401(k) Savings Plan


Savings Plan Highlights and FAQs


Advocacy Services 



Dental Plan Summary
Learn More About Dental Benefits
Dental Insurance Overview 
Dental PPO - Facts & Stats

Life Insurance Optional Life Plan Summary
Long-Term Disability  Valuable Benefits 

Medical - BCBS  2019 BCBS Enrollment Guide 
Understanding Your Explanation of Benefits
Children's Wellness Guidelines
Adult Wellness Guidelines
Summary of Benefits and Coverage:      Basic/Enhanced
Medical - Kaiser  

2019 Enrollment Guide

How Kaiser Permanente helps you thrive

It's easy to get started with Kaiser Permanente

Kaiser Permanente Healthy Resource Guide

Kaiser Permanente Care Away from Home

Kaiser Permanente Mobile Tools 

Summary of Benefits and Coverage:    

CA - Basic/Enhanced

CO - Basic/Enhanced

DC - Basic/Enhanced

GA - Basic/Enhanced 


MD - Basic/Enhanced

OR - Basic/Enhanced

VA - Basic/Enhanced  

WA - Basic/Enhanced  

OptumRx Utilization Management Updates

Digital Tools

Formulary Updates            

2019 Formulary 


Basic Option Benefit Summary
Premier Option Benefit Summary 

WorkLife Solutions (EAP)

Benefits Summary 
Online Will

Your Spending Account (YSA)


Alight Smart-Choice Options