Our Mission

Our vision is to supplant COBRA while providing all employees in the U.S. with a better safety net and experience when transitioning between jobs.

We founded When in 2020 and it has always been about helping people afford health insurance after a job loss. Through personal experience we realized the end of the employee lifecycle was often neglected. Our aim has been to change the exit process. Off-boarding should be valued as much as onboarding. The last impression is often the most important.

With backgrounds that include marketing, consulting, finance, and computer science, guess the one universal experience that our entire team shares: losing our job and suddenly having to face the steep costs of COBRA coverage.

The cost of COBRA and the confusion around shopping for health insurance are common American problems for workers. We want to fix it. We help employers provide exiting employees a smoother and personalized transition experience. We help people continue to afford health insurance during a job transition.

When is about partnering with employers to ensure exiting employees have the support they need to find affordable alternatives to COBRA.

Our Team

Andy Hamilton

CEO and Co-founder

Andy has built two separate technology companies that were acquired by public companies, the most recent, ApartmentJet, was

acquired by Expedia Group in 2018. After getting laid off during Covid, Andy joined with Dan to supplant COBRA and provide employees a better experience when transitioning between jobs.

Read More

Dan Wertheimer

CSO and Co-founder

Dan is the originator of the idea for When where he developed the original business model and case while getting his MBA at University

of Chicago Booth School of Business. Prior to starting When, Dan led the innovation and accelerator programs at Target and Discover. During Covid, Dan teamed up with Andy to implement his vision for fixing post-employment health insurance.

Read More

Patrick Koeller


Patrick is a seasoned CTO, has a history of guiding startups to success, notably leading one to acquisition by Expedia. At When

his extensive expertise in Gen AI and technology platform development ensures partners receive innovative and efficient solutions.

Read More

Kristy Loeffler


Kristy comes to When with a proven track record in the tech industry and start-up ecosystem. Strategic financial leader adept at driving

growth, optimizing operations, and securing funding for high-growth companies with an eye on supporting business objectives and maximizing shareholder value.

Read More

Jeremy Leon

Head of Product

As a former actuary and benefits manager, Jeremy brings over a decade of experience in the HR and benefits industry to his role as

Head of Product at When. Jeremy began his career as a Health & Benefits Analyst at Mercer, where he gained expertise in actuarial analysis and financial modeling. Subsequently, Jeremy managed benefit programs at Tesla and Included Health, gaining deep knowledge of benefits program management, HR systems, HR operations, and more.

Read More

Jordan Scheiber

Head of Sales

With over 14 years of experience in the insurance and risk analysis industry, I have a proven track record of exceeding sales quotas, growing

revenue, and building long-term relationships with C-level executives and HR teams.

Read More


Girish Gehani

COO, Trilogy Real Estate Group

Liz Smith

President, Midwest, MMA

Beth Turbitt

Managing Director, Aon

Tracy Desmond

Head of Global Benefits & Wellbeing, AirBnB

Alex Seiler

Chief People Officer and Start-Up Advisor

Angela Niemann

Senior Vice President, Legal, Expedia Group

Jeff Bahrenburg

Executive Vice President, SF Bay Area, USI


B Capital Group

Network Ventures

Enfield Capital

When is the best-case scenario for the worst-case scenario

When protects your employee’s ability to pay for health insurance coverage after an involuntary job loss.

Employee-first wellness

Access to health insurance is a basic need. A safety net for employees beyond employment.

Simplifying complex benefits

When is the perfect complement to your insurance offering. We help your employees navigate the complexities of today’s insurance landscape.

Here for the hard times

Losing a job shouldn’t mean losing insurance. When provides much-needed peace of mind around health benefits.

Want to Protect Your Employees?

Get in touch with someone on our team to learn how you can bring this new benefit to your company.
Scroll to Top