When for Medicare

From group coverage to Medicare confidence.

When partners with employers to proactively support employees approaching Medicare eligibility.

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Smiling man in a grey blazer and graphic tee, lit by window shadows on a beige wall

When for Medicare

We handle the expertise so your HR doesn't have to become experts.

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Medicare Education Hub

A learning center with resources that makes Medicare understandable for every employee, regardless of their situation.

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Medicare Education Hub

A learning center with resources that makes Medicare understandable for every employee, regardless of their situation.

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Medicare Education Hub

A learning center with resources that makes Medicare understandable for every employee, regardless of their situation.

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Licensed Medicare Advisors

Employees can schedule 1:1 consultations with licensed Medicare agents who help finalize decisions, select plans, and handle enrollment.

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Licensed Medicare Advisors

Employees can schedule 1:1 consultations with licensed Medicare agents who help finalize decisions, select plans, and handle enrollment.

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Licensed Medicare Advisors

Employees can schedule 1:1 consultations with licensed Medicare agents who help finalize decisions, select plans, and handle enrollment.

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Customized Webinars

Scalable Medicare education delivered through webinar series that address common questions and reduce one-off inquiries to HR.

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Customized Webinars

Scalable Medicare education delivered through webinar series that address common questions and reduce one-off inquiries to HR.

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Customized Webinars

Scalable Medicare education delivered through webinar series that address common questions and reduce one-off inquiries to HR.

The Right Plan at the Right Time

The Right Plan at the Right Time

For active employees nearing eligibility, we educate early. For departing employees, our platform automatically surfaces Medicare options as an alternative to COBRA — so they land in the right plan, not the expensive one.

For active employees nearing eligibility, we educate early. For departing employees, our platform automatically surfaces Medicare options as an alternative to COBRA — so they land in the right plan, not the expensive one.

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Working Past 65

Employees approaching 65 who are still working need to understand how Medicare interacts with employer coverage.

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Working Past 65

Employees approaching 65 who are still working need to understand how Medicare interacts with employer coverage.

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Retiring at 65

Employees retiring at or after 65 need to transition from employer coverage to Medicare without gaps, penalties, or disruption to their care.

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Retiring at 65

Employees retiring at or after 65 need to transition from employer coverage to Medicare without gaps, penalties, or disruption to their care.

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Coverage for Family

Dependents who need guidance or their own indvidual coverage when the primary moves to Medicare.

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Coverage for Family

Dependents who need guidance or their own indvidual coverage when the primary moves to Medicare.

How It Works

From case creation to enrollment.

Connect via HRIS integration or share a simple data file. Either way, we'll identify employees approaching Medicare eligibility to begin outreach.

STEP 1
We Receive Case Data

Your team sends employee case files to When. We create cases for employees who are retiring or approaching Medicare eligibility.

STEP 2
Employees Get Invited

Eligible employees receive personalized emails inviting them to create their When account and access Medicare resources.

STEP 3
Explore the Medicare Center

Inside the When portal, employees can explore our education hub, browse FAQs, and stay on top of critical enrollment deadlines.

STEP 4
Schedule a 1:1 Consultation

Employees book time with a licensed advisor who walks them through their options and helps them enroll in the right plan when they are ready.

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Continuous Innovation

We’ll keep releasing new features, refining automation, and enhancing performance based on user feedback.

Frequently asked questions

Does When sell Medicare plans?

No. When provides education and enrollment support — we're not a Medicare sales organization. Our licensed specialists help employees understand their options and enroll in the plan that's right for them, with no bias toward a specific carrier.

Is there a cost to employees?

No. When's Medicare support services are fully employer-sponsored. Employees access the platform, consultations, and webinars at no cost to them.

Can employees access support outside of open enrollment?

Yes. The platform, educational resources, and licensed specialists are available year-round — not just during enrollment windows.

How is this different from a Medicare broker?

Traditional Medicare brokers work with individuals who seek them out. When integrates directly with your employer systems to proactively identify and reach eligible employees before they're confused or missing deadlines — meeting them where they already are.

How long does implementation take?

Most employers are up and running within a few weeks. When integrates with your existing HRIS, and our team handles the setup and employee communications.

Does When support employees in all 50 states?

Yes. Our licensed Medicare specialists can support employees nationwide, regardless of where they live or plan to retire.

If you have any further questions or just want to reach our team, click the button below.