When Blog: COBRA, Medicare & Workforce Transitions

Advisory Firm vs. Licensed Agency: Who Can Actually Enroll? — a glowing licensed-agency seal with a checkmark and ribbons.

Insight

Jul 15, 2026

Advisory Firm vs. Licensed Agency: Who Can Actually Enroll?

Dan Wertheimer

It's Not If, It's When: Build Your Off-Boarding Plan Before You Need It

The Best Cost-Containment Solution Is the One You Can Implement the Fastest

Your Aging Workforce Is a Benefits Cliff. Here's the Data.

Why Our Agents Don't Work on Commission

Get When’s insights in your inbox

Sharp takes on workforce transitions, COBRA, Medicare, and healthcare costs.

By subscribing you agree to our Privacy Policy.

Insight

Jun 1, 2026

What HR Can and Can’t Say About Medicare (Without a License)

Dan Wertheimer

Insight

Jun 1, 2026

What HR Can and Can’t Say About Medicare (Without a License)

Dan Wertheimer

Insight

Jun 1, 2026

What HR Can and Can’t Say About Medicare (Without a License)

Dan Wertheimer

Insight

May 21, 2026

The Captive Blind Spot at the Exit Door

Tom Cox

Insight

May 21, 2026

The Captive Blind Spot at the Exit Door

Tom Cox

Insight

May 21, 2026

The Captive Blind Spot at the Exit Door

Tom Cox

Insight

May 19, 2026

Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.

Tom Cox

Insight

May 19, 2026

Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.

Tom Cox

Insight

May 19, 2026

Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.

Tom Cox

Insight

Apr 14, 2026

"Our Plan Is Too Rich. They'll Always Choose COBRA."

Carly Keller

Insight

Apr 14, 2026

"Our Plan Is Too Rich. They'll Always Choose COBRA."

Carly Keller

Insight

Apr 14, 2026

"Our Plan Is Too Rich. They'll Always Choose COBRA."

Carly Keller

News

Apr 8, 2026

P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients

Tom Cox

News

Apr 8, 2026

P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients

Tom Cox

News

Apr 8, 2026

P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients

Tom Cox

Stories

Mar 27, 2026

The Salary Number Everyone Sees. The Health Insurance Gap Nobody Talks About.

Andy Hamilton

Stories

Mar 27, 2026

The Salary Number Everyone Sees. The Health Insurance Gap Nobody Talks About.

Andy Hamilton

Stories

Mar 27, 2026

The Salary Number Everyone Sees. The Health Insurance Gap Nobody Talks About.

Andy Hamilton

Insight

Mar 17, 2026

AI in Employee Benefits: From Chatbot Curiosity to the Most Important Decision Your Departing Employees Will Ever Make

Tom Cox

Insight

Mar 17, 2026

AI in Employee Benefits: From Chatbot Curiosity to the Most Important Decision Your Departing Employees Will Ever Make

Tom Cox

Insight

Mar 17, 2026

AI in Employee Benefits: From Chatbot Curiosity to the Most Important Decision Your Departing Employees Will Ever Make

Tom Cox

Insight

Mar 12, 2026

Americans Are Rationing Medicine to Afford Health Care. Employers Can't Look Away.

Andy Hamilton

Insight

Mar 12, 2026

Americans Are Rationing Medicine to Afford Health Care. Employers Can't Look Away.

Andy Hamilton

Insight

Mar 12, 2026

Americans Are Rationing Medicine to Afford Health Care. Employers Can't Look Away.

Andy Hamilton