2018 Annual Enrollment

The Annual Enrollment Period for 2018 benefits is: October 25 through November 8, 2017

Important Notes:  

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 - 2018):*

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

In addition, all associates must “refresh” their spouse surcharge and tobacco credit elections. None of these elections will carry over from 2017. Although optional life insurance coverage automatically rolls over into 2018, 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 2017 Fall Benefits Newsletter (rev.):  English I Spanish and consider the "Actions to Take Before Annual Enrollment" sections for medical and prescription drug coverage.

  • Update your home address 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 25 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 8.
  • Consider the insurance carriers and levels to minimize increases to your medical cost. It's important for you to actively choose medical coverage during Annual Enrollment. Otherwise, you will not have medical or prescription coverage for 2018. 
  • Use the various tools and resources listed in the 2017 Fall Benefits Newsletter (rev.):  English I Spanish. Sears Holdings Corporation (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.
  • Take a close look at all of your available benefits for 2018. Whether you’re considering the Basic option for the first time, or revisiting the Health Savings Account (HSA), the Flexible Spending Accounts (FSA), or the Sears Holdings 401(k) Savings Plan, decide what is right for you and your family. 
  • 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 statement available in your Secure Participant Mailbox  on YBR within two business days of enrollment. Make sure your confirmation statement accurately reflects the elections you made during Annual Enrollment. If your confirmation statement does not reflect your enrollment choices, you should immediately contact the Sears Holdings Benefits Center at 1.888.88sears (1.888.887.3277).

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 25:
    • 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.


  • 2017 Fall Benefits Newsletters (rev.): English I Spanish

  • 2017 Fall Benefits Newsletter - Rx Page 5 (rev.): English

  • 2018 Annual Enrollment: FAQs

  • Additional Resources: 

401(k) Savings Plan


401(k) Savings Plan Highlights and FAQs

401(k) Savings Plan Financial Advisors


Advocacy Services Introduction

Advocacy Services Checklist 

EyeMed Vision Plan


Basic Option Benefit Summary

Premier Option Benefit Summary

Life Insurance LifeSuite Services
How much insurance do I need?
Importance of Beneficiary Designation 
Optional Life Enrollment
Long-Term Disability  Valuable Benefits

MetLife Dental

Dental Plan Summary 

WorkLife Solutions

Benefits Summary 
Legal & Financial Services

Your Spending Account (YSA)


Commuter Benefits Brochure

FSA Brochure

HSA Brochure            

Mobile App

Text Messaging