We Are When

A culture of compassion, innovation, and support.

When is pioneering the future of workforce transitions through AI-powered solutions that support employees during life's most critical moments. Founded with the belief that every career transition deserves thoughtful care, we're transforming how employers handle departures, retirements, and life events with modern, compliant alternatives to traditional COBRA coverage.

01 Empathy

With personal experiences of job loss, our team deeply understands the challenges and importance of a supportive offboarding process.

01 Empathy

With personal experiences of job loss, our team deeply understands the challenges and importance of a supportive offboarding process.

Employees Supported Across 6,200+ Companies

03 Collaboration

We work closely with employers to tailor our offerings to their unique needs, fostering strong partnerships built on trust and shared goals.

03 Collaboration

We work closely with employers to tailor our offerings to their unique needs, fostering strong partnerships built on trust and shared goals.

75K

Employee Life Events Cases Managed

02 Commitment

We constantly strive to deliver the best solutions and services to our clients and their exiting employees, ensuring a smooth transition.

02 Commitment

We constantly strive to deliver the best solutions and services to our clients and their exiting employees, ensuring a smooth transition.

$5M+

Managed Cash Benefits for Health Coverage

Leadership Team

Andy Hamilton

Founder & CEO

Serial entrepreneur and multifamily tech veteran who co-founded and led ApartmentJet through its successful acquisition by Expedia Group, where he subsequently ran operations for their multifamily division.

Andy Hamilton

Founder & CEO

Dan Wertheimer

Founder & CSO

Fortune 50 innovation executive who led Target's digital transformation as Senior Director of Innovation, building their marketplace strategy and managing their global accelerator portfolio including Target + Techstars and Target Takeoff.

Dan Wertheimer

Founder & CSO

Patrick Koeller

CTO

Technical co-founder and proven engineering leader with a track record of scaling startups to successful exits, including building Print Syndicate to $40M in annual revenue and orchestrating ApartmentJet's acquisition by Expedia Group.

Patrick Koeller

CTO

Brett Cable

CFO

Former CFO and Chief Data & Analytics Officer at Tandem HR who played a pivotal role in its acquisition by Vensure, bringing deep PEO expertise and data-driven financial leadership to When's growth strategy.

Brett Cable

CFO

Jeremy Leon

Head of Product

Former actuary and HR/Benefits expert at Tesla and Mercer who designed benefit plans and managed costs for enterprise clients and thousands of employees.

Jeremy Leon

Head of Product

Former actuary and HR/Benefits expert at Tesla and Mercer who designed benefit plans and managed costs for enterprise clients and thousands of employees.

Carly Keller

Director of Client Operations

Naval Academy graduate and former Navy officer who led Operations at ApartmentJet through its Expedia acquisition, where she then built and managed large client service teams at Expedia.

Carly Keller

Director of Client Operations

Naval Academy graduate and former Navy officer who led Operations at ApartmentJet through its Expedia acquisition, where she then built and managed large client service teams at Expedia.

News & Insights

Read the latest product updates, company news and industry insight.

Insight

Feb 24, 2026

COBRA Is a Known Underwriting Problem. When Is the Solution Carriers Haven't Had.

Tom Cox

COBRA Administrators: From Compliance Vendor to Strategic Partner

How PEOs Are Turning Offboarding into a Competitive Edge

Why Proactive Medicare Support Delivers ROI

When Raises $10M Series A: Building the Bridge Across America's Healthcare Gap