Coverage Transition Management

Own the moment coverage changes.

When™ is the enterprise platform for guided health insurance decisions at every qualifying life event. We close the gap COBRA leaves open, uncover significant cost savings, and give every departing employee a personalized experience. Nothing changes for your team or your benefits ecosystem.

Schedule a Demo

Schedule a Demo

Confident HR & Benefits Leader
Employee finding health insurance plans on When platform
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Trusted by Fortune 50 and Fortune 500 employers

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Trusted by Fortune 50 and Fortune 500 employers

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Trusted by Fortune 50 and Fortune 500 employers

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The Blind Spot

Employers perfect day one.
No one owns the last day.

You inherited COBRA, a 40-year-old law written for a workforce that stayed put. It makes the exit compliant. It doesn’t manage it, and the gap between ‘the notice went out’ and ‘the person landed somewhere’ is where million-dollar claims live.

Annual U.S. transitions

60M+

Workforce transitions every year (BLS JOLTS)

COBRA Participants

15x

More $1M claims than active employees (Tokio Marine HCC)

Healthcare Costs

6.7%

Employer health cost increase in 2026, the highest in 15 years (Mercer)

Annual U.S. transitions

60M+

Workforce transitions every year (BLS JOLTS)

COBRA Participants

15x

More $1M claims than active employees (Tokio Marine HCC)

Healthcare Costs

6.7%

Employer health cost increase in 2026, the highest in 15 years (Mercer)

The When Solution

Every other cost lever forces a tradeoff between your CFO and your people. This one doesn’t.

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Lower Claims, Better Renewals

The members most likely to elect COBRA are the ones most likely to blow through your stop-loss deductible. When they land somewhere else, their claims never reach your plan, your stop-loss carrier, or next year’s baseline.

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Lower Claims, Better Renewals

The members most likely to elect COBRA are the ones most likely to blow through your stop-loss deductible. When they land somewhere else, their claims never reach your plan, your stop-loss carrier, or next year’s baseline.

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Lower Claims, Better Renewals

The members most likely to elect COBRA are the ones most likely to blow through your stop-loss deductible. When they land somewhere else, their claims never reach your plan, your stop-loss carrier, or next year’s baseline.

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A Decision, Not a Packet

Departing employees get a modern experience instead of a twenty-page packet that shows up weeks after they leave. Licensed, non-commissioned agents walk them through every real option, including COBRA.

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A Decision, Not a Packet

Departing employees get a modern experience instead of a twenty-page packet that shows up weeks after they leave. Licensed, non-commissioned agents walk them through every real option, including COBRA.

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A Decision, Not a Packet

Departing employees get a modern experience instead of a twenty-page packet that shows up weeks after they leave. Licensed, non-commissioned agents walk them through every real option, including COBRA.

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Nothing Changes for Your Team

When slips into your existing workflow. Nothing changes for a single active employee, your carrier, your COBRA vendor, your benefits admin, or your team’s workload.

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Nothing Changes for Your Team

When slips into your existing workflow. Nothing changes for a single active employee, your carrier, your COBRA vendor, your benefits admin, or your team’s workload.

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Nothing Changes for Your Team

When slips into your existing workflow. Nothing changes for a single active employee, your carrier, your COBRA vendor, your benefits admin, or your team’s workload.

See How It Works

See How It Works

Built for employers who want to manage the exit, not just check a compliance box

Most employers should have a coverage transition strategy. If two or more of these sound familiar, it’s time.

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Carrying COBRA Claims

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RIFs and Layoffs

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Continuous Optimization

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Medicare-Eligible Population

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    Carrying COBRA Claims

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    RIFs and Layoffs

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    Continuous Optimization

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    Medicare-Eligible Population

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    Carrying COBRA Claims

  • Employee needing Medicare navigation
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    RIFs and Layoffs

  • Employee after voluntary exit and considering COBRA
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    Continuous Optimization

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    Medicare-Eligible Population

Licensed in all 50 states

Explore Solutions

Explore Solutions

One platform, three products

Smart enough to personalize, human enough to care. Technology, licensing, and licensed, non-commissioned agents, built for the moment coverage changes.

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When™ Next
Decision support at every loss of coverage
COBRA and alternatives, side by side
An optional Employer Contribution for the plan they choose
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When™ Next
Decision support at every loss of coverage
COBRA and alternatives, side by side
An optional Employer Contribution for the plan they choose
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When™ Medicare
Proactive education starting at 64½
One-on-one guidance before enrollment
Medicare questions off HR’s desk
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When™ Medicare
Proactive education starting at 64½
One-on-one guidance before enrollment
Medicare questions off HR’s desk
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When™ Choice
Broker-aligned ICHRA solution
Affordability testing through automated premium payments
A fixed, predictable cost instead of a renewal surprise
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When™ Choice
Broker-aligned ICHRA solution
Affordability testing through automated premium payments
A fixed, predictable cost instead of a renewal surprise

Explore Platform

Explore Platform

A woman on the phone with When getting Medicare enrollment support
A woman on the phone with When getting Medicare enrollment support
A woman on the phone with When getting Medicare enrollment support

The cost savings were significant, but the real victory is in the peace of mind we've provided our departing colleagues.

HR Executive

Insights on coverage transition management

Insight

Oct 5, 2026

Few Exits, Expensive Exits: The COBRA Problem Hiding in Stable Workforces

Tom Cox

Insight

Oct 5, 2026

Few Exits, Expensive Exits: The COBRA Problem Hiding in Stable Workforces

Tom Cox

Insight

Oct 5, 2026

Few Exits, Expensive Exits: The COBRA Problem Hiding in Stable Workforces

Tom Cox

Dark plum blog header with the When tulip and the eyebrow "Severance · the math." Headline: "Cash or coverage? Run the math." Subheading: "Cash severance loses 35% before it lands." On the right are two gold coin stacks. The "Cash" stack is labeled "$2,110 lands," and its top third is shown as dashed ghost coins bracketed "TAX." The "Benefit" stack is solid all the way up and labeled "$3,000 lands."

Insight

Sep 29, 2026

Cash Severance vs. a Healthcare Benefit: The Math Most Companies Don't Run

Andy Hamilton

Dark plum blog header with the When tulip and the eyebrow "Severance · the math." Headline: "Cash or coverage? Run the math." Subheading: "Cash severance loses 35% before it lands." On the right are two gold coin stacks. The "Cash" stack is labeled "$2,110 lands," and its top third is shown as dashed ghost coins bracketed "TAX." The "Benefit" stack is solid all the way up and labeled "$3,000 lands."

Insight

Sep 29, 2026

Cash Severance vs. a Healthcare Benefit: The Math Most Companies Don't Run

Andy Hamilton

Dark plum blog header with the When tulip and the eyebrow "Severance · the math." Headline: "Cash or coverage? Run the math." Subheading: "Cash severance loses 35% before it lands." On the right are two gold coin stacks. The "Cash" stack is labeled "$2,110 lands," and its top third is shown as dashed ghost coins bracketed "TAX." The "Benefit" stack is solid all the way up and labeled "$3,000 lands."

Insight

Sep 29, 2026

Cash Severance vs. a Healthcare Benefit: The Math Most Companies Don't Run

Andy Hamilton

Dark plum blog header. Headline reads "Not on the report. Still on the plan," above an eyebrow with the When tulip that says "COBRA · the hidden cost." On the right, a "High-Cost Claimant Report" panel lists dim data columns — Claimant, Diagnosis, Paid — beside a highlighted, dashed-outlined "STATUS?" column, with a glowing amber dollar-sign coin sitting in that column to represent the hidden COBRA cost the report leaves out.

Insight

Jul 28, 2026

COBRA Doesn't Show Up on the Plan Report. That's Why It Keeps Costing You.

Tom Cox

Dark plum blog header. Headline reads "Not on the report. Still on the plan," above an eyebrow with the When tulip that says "COBRA · the hidden cost." On the right, a "High-Cost Claimant Report" panel lists dim data columns — Claimant, Diagnosis, Paid — beside a highlighted, dashed-outlined "STATUS?" column, with a glowing amber dollar-sign coin sitting in that column to represent the hidden COBRA cost the report leaves out.

Insight

Jul 28, 2026

COBRA Doesn't Show Up on the Plan Report. That's Why It Keeps Costing You.

Tom Cox

Dark plum blog header. Headline reads "Not on the report. Still on the plan," above an eyebrow with the When tulip that says "COBRA · the hidden cost." On the right, a "High-Cost Claimant Report" panel lists dim data columns — Claimant, Diagnosis, Paid — beside a highlighted, dashed-outlined "STATUS?" column, with a glowing amber dollar-sign coin sitting in that column to represent the hidden COBRA cost the report leaves out.

Insight

Jul 28, 2026

COBRA Doesn't Show Up on the Plan Report. That's Why It Keeps Costing You.

Tom Cox

"Employers are looking for new and creative ways to enhance their offerings to help attract and retain employees. Those who partner with When will stand out when competing for talent."

Tracy D

Head of Global Benefits & Wellbeing

"Employers are looking for new and creative ways to enhance their offerings to help attract and retain employees. Those who partner with When will stand out when competing for talent."

Tracy D

Head of Global Benefits & Wellbeing

"Employers are looking for new and creative ways to enhance their offerings to help attract and retain employees. Those who partner with When will stand out when competing for talent."

Tracy D

Head of Global Benefits & Wellbeing