How to Get Started with StretchDollar (Employees)


Guide for Employees

StretchDollar offers a new way for small employers and their people to access health insurance that provides more flexibility for everyone. 

First, some basics: how StretchDollar works

With StretchDollar, your employer provides you pre-tax dollars every month to reimburse you for the premiums you pay for a health insurance plan you choose from the marketplace. StretchDollar offers these pre-tax benefits through an ICHRA or individual coverage health reimbursement arrangement. Learn all the nitty gritty details about ICHRAs in our Not-So-Boring Guide to ICHRA.


StretchDollar also helps employees find the perfect health plan if they need assistance. (We've got you covered.)

Getting started with StretchDollar

You should have received two emails from StretchDollar. You’ll need these emails to access your account and get started. These include:

  • Your Benefits Portal account verification and access. (This is what you’ll use to access the portal to submit reimbursement requests for your premium costs.)
  • Your Welcome email that includes a link to start shopping for health plans on the marketplace.

IMPORTANT!  You cannot accept your employer’s StretchDollar health benefit dollars AND receive a premium tax credit. Not sure if you’re eligible for a premium tax credit? Find out before you enroll with this calculator.

What’s a premium tax credit? It's a discount to help individuals and families afford health insurance. The tax credit is provided by the government to help people pay for the premiums of health insurance plans purchased on the marketplace. Click here to learn more.

Set up your Benefits Portal in 5 steps

#1 Sign in and set a password!

You should have received an email inviting you to join your company in the StretchDollar Benefits Portal. Can’t find your invite? Check your spam folder!


Click the link and immediately set your own password. If you don’t set up a password and try to do it later, you may be unable to log in.

Trouble logging in? We walk you through the steps here.

#2 Time for a quick Q&A.

After setting a password, we'll ask you a few questions about yourself. This helps us provide you the guidance you want or need. Questions will include:

  • Basic info like your name, phone number and home zip code
  • If you want to enroll, waive or learn more about your StretchDollar health benefit
  • How you'd like us to communicate with you (phone, email, etc.)

If you select “waive,” you’re all done. No further action is needed!


If you select "I want to enroll" or "I want to learn more" you'll be directed to either shop for a health plan on the marketplace or book an appointment with one of our licensed brokers. (You can also do that by reaching out to brokers@stretchdollar.com.)

#3 Link your bank account.

This is the bank account where your health benefit dollars will be deposited once you request reimbursement from your employer. 

  1. Select "Bank Setup" from the left-side navigation.
  2. Click  the “Connect Bank” button and follow the directions. (Note: If your bank is not listed, follow these instructions for a manual setup.)


You’ll receive an email that confirms your bank account was successfully added.


#4 Shop and purchase a health plan on the marketplace.

(Already have a health plan purchased from the individual marketplace? Skip this step and move to #5.)

Select "shop" in the left side navigation. You'll answer a few questions to direct you to your state's marketplace.


Remember, your health benefit dollars will not be included in the health plan premium price you see while shopping. You’ll have to do a little bit of math to figure out your total out-of-pocket cost each month. (Monthly premium MINUS your StretchDollar benefit dollars = total monthly cost to you.)

Important! You can't accept your employer's StretchDollar benefit dollars and a premium tax credit. Not sure if you're eligible for a tax credit? Find out before you enroll with this calculator.


What to expect when shopping on the marketplace

  • Enter personal details. You’ll need to include age, social security number and zip code for yourself and anyone else you’ll be covering under your plan. 
  • Household income question. This is to see if you qualify for a premium tax credit. Want to check before you shop if you qualify? Use this calculator. Remember: You cannot accept your employer’s StretchDollar health benefit and a premium tax credit. See more helpful info here.
  • Question about tobacco use. 
  • Proof of qualifying life event. When you are newly eligible for StretchDollar ICHRA benefits, you are able to enroll in health coverage through something called a “qualifying life event”. This is a fancy term that means that you are allowed to enroll in health care coverage outside of open enrollment.  If you get asked for proof of that qualifying life event, the Employee Notice is that proof, which can be found in the Documents tab of your Benefits Portal. 
    • Note: Use the Employee Notice to find your ICHRA plan start date as well as the date you were notified about your health benefit.

You must pay your first month's premium to make the health plan active. The next step will detail how to get reimbursed for that first premium payment and going forward.

#5 Enroll in Auto Reimbursements tab.

Once you have purchased a health plan and received an invoice, the next step is to set up auto-reimbursements for your premium payments. Follow the steps below to have your health benefit dollars sent to your bank account around the first business day of every month. You must have your health plan invoice to complete this step.

  1. Click Auto-Reimbursement (#1)
  2. Select "Set up Auto-Reimbursement" (#2)
  3. Complete the information in the form and upload your invoice (#3)
  4. An email will be sent to your Admin to review your request. Once approved, you're all done!

Note: You may need to also submit a one-time reimbursement. Funds are drawn from the business bank account on the 25th of the month for distributions around the 1st. If your request is approved on the 25th or later, your automatic reimbursements will start on the 1st of the second following month. For example, if you enroll on Feb 26, you'll also need to submit a one-time reimbursement for March, as your automatic reimbursements will start April 1. 

What happens next? 

Your admin will get an email alert to review the enrollment application. Once approved, you can kick back and relax - your benefit dollars will be deposited into your bank account around the first business day of each month for the rest of the plan year, like clockwork.


Have questions? Contact your StretchDollar team at support@stretchdollar.com.

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