How to Get Started with StretchDollar (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.

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.

#2 Let StretchDollar walk you through enrollment.

When you sign in, StretchDollar walks you through enrollment one step at a time: your details, choosing a plan, proof of coverage, and connecting the bank account where your reimbursements go. Once you've finished enrollment or waived your allowance, you'll see your dashboard and the full menu, including Reimbursements and Documents. If you land back in enrollment when you sign in, a step is still open, so pick up where you left off. When it's time to renew, you'll see "It's time to pick your 2027 plan." Click Start my renewal to begin.

To start, click Get started and confirm your details: about you, who needs health plan coverage, and where you live. Your ZIP code decides which plans you can buy.

Don't need the allowance? On the plans page, click Next step, choose I want to waive my allowance, pick the reason that fits and click Confirm waive. Waived by mistake or had a change? Email support@stretchdollar.com or start a chat. Only the StretchDollar team can undo a waiver.

Want help choosing a plan? Book an appointment with one of our licensed brokers by reaching out to brokers@stretchdollar.com.

#3 Choose and buy a health plan.

(Already have a health plan? On the plans page, click Next step, choose I already enrolled in a plan, tell us how you're covered, then upload your proof of coverage in step #4.)

You'll see plans for your ZIP code. Every price on the plans page shows your estimated cost after your employer's reimbursement. If you shop on a marketplace or insurance company website instead, those prices don't include your StretchDollar benefit dollars, so you'll have to do a little bit of math. (Monthly premium MINUS your StretchDollar benefit dollars = total monthly cost to you.)

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.

#4 Send us your proof of coverage.

Once you have purchased a health plan and received an invoice, come back to StretchDollar and send us your proof of coverage. This sets up your auto-reimbursements, so your health benefit dollars are sent to your bank account around the first business day of every month. You'll need proof of coverage to complete this step, such as an invoice, an enrollment confirmation, or a screenshot from your insurance portal.

1. On the plans page, click Next step, choose I already enrolled in a plan, and tell us how you're covered.
2. Upload your proof of coverage (such as an invoice) and check the plan details: insurance carrier, monthly premium and when your coverage starts.
3. Answer how you paid for your premium, tick the confirmations and click Submit.

#5 Connect your bank account.

This is the bank account where your health benefit dollars will be deposited. Click Connect bank account and follow the directions. (Note: If your bank is not listed, follow these instructions for a manual setup.) When you're done, you'll see how your month breaks down. Click Go to my dashboard. An email will be sent to your Admin to review your request. Once approved, you're all done!

After enrollment: use Bank Setup in the menu to change your bank account, and Auto-Reimbursements to check your auto-reimbursement.

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.

Massachusetts and Rhode Island: if you live in Massachusetts or Rhode Island, auto-reimbursements go out on the 16th instead of the 25th, because insurers there need payment by the 23rd or 24th. Submit your enrollment application and proof of coverage by the 15th, and your auto-reimbursement goes out on the 16th. Both steps are for coverage that starts on the 1st of the next month.

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