When Blog: COBRA, Medicare & Workforce Transitions
Insight
PEPM Is Predictable. Utilization Is Aligned. Why We Offer Both.
Brook West
COBRA Qualifying Events: The Full List Beyond Layoffs
Advisory Firm vs. Licensed Agency: Who Can Actually Enroll?
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
Insight
Your Aging Workforce Is a Benefits Cliff. Here's the Data.
Carly Keller
Stories
Why Our Agents Don't Work on Commission
Dan Wertheimer
Insight
What HR Can and Can’t Say About Medicare (Without a License)
Dan Wertheimer
Insight
The Captive Blind Spot at the Exit Door
Tom Cox
Insight
Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.
Tom Cox
Insight
"Our Plan Is Too Rich. They'll Always Choose COBRA."
Carly Keller
News
P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients
Tom Cox
Stories
The Salary Number Everyone Sees. The Health Insurance Gap Nobody Talks About.
Andy Hamilton
Insight
AI in Employee Benefits: From Chatbot Curiosity to the Most Important Decision Your Departing Employees Will Ever Make
Tom Cox
Insight
Americans Are Rationing Medicine to Afford Health Care. Employers Can't Look Away.
Andy Hamilton
Insight
COBRA Is a Known Underwriting Problem. When Is the Solution Carriers Haven't Had.
Tom Cox
Insight
COBRA Administrators: From Compliance Vendor to Strategic Partner
Jeremy Leon
Insight
How PEOs Are Turning Offboarding into a Competitive Edge
Dan Wertheimer
Insight
Why Proactive Medicare Support Delivers ROI
Carly Keller
News
When Raises $10M Series A: Building the Bridge Across America's Healthcare Gap
Andy Hamilton
Insight
Your COBRA Subsidy Is Costing You Double. Here's the Fix.
Insight
How to Update Your Severance Policy Without the Drama: A Practical Guide
Jeremy Leon
Insight
How Self-Funded TPAs Can Help Clients Reduce COBRA Claims Exposure
Tom Cox
Insight
COBRA Is Your Most Underleveraged Service Line — How Benefits TPAs Can Change That
Tom Cox
Stories
The Story of When: Two neighbors' mission to fill America's Healthcare Gap.
Patrick Koeller
Insight
How COBRA Is Quietly Driving Up Healthcare Costs for Self-Insured Employers
Andy Hamilton
News
When CEO Andy Hamilton Featured in "All the Cool Girls Get Fired"
Carly Keller
Stories
A When Story - Meet Nicole
Carly Keller
News
When Partners with Iowa State University, Helping Graduates Navigate Health Insurance
Carly Keller
Insight
The Hidden Costs of Poor Employee Offboarding
Andy Hamilton
Insight
COBRA’s Mid-Life Crisis Hits at 39
Patrick Koeller
Insight
The True Cost of Offboarding: A Look Beyond the Last Paycheck
Patrick Koeller
Insight
The Rise of Revenge Quitting: Why Employees Are Taking a Stand in 2025
Dan Wertheimer
Insight
Buyouts vs Layoffs: A Complete Guide to Workforce Reduction Options
Andy Hamilton
Insight
The Future of Healthcare: Finding Your Place in the Medical Revolution
News
2024 Year in Review: A Year of Better Healthcare Choices
Andy Hamilton
News
When Welcomes Tara Conger to Board of Directors
Dan Wertheimer
Insight
Client Saved $1.4M in 3 Months with When’s Workforce Transitions Platform
Carly Keller
Insight
Picking Insurance Plans with When
Patrick Koeller
Insight
What is COBRA?
Dan Wertheimer
Insight
What is Health Insurance?
Jeremy Leon
Stories
The Birth of When
Andy Hamilton