Our Mission
Empower people to navigate benefit decisions through trusted, unbiased support.
When is pioneering the future of workforce transitions through intelligent 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.
1M
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
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.
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
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.
Brook West
Chief Revenue Officer
Veteran SaaS commercial leader with two decades scaling healthcare and technology revenue organizations, holding senior leadership roles at Carrum Health, 98point6, Valant, and Fuze while building teams from early stage to category leadership.
Brook West
Chief Revenue Officer
Veteran SaaS commercial leader with two decades scaling healthcare and technology revenue organizations, holding senior leadership roles at Carrum Health, 98point6, Valant, and Fuze while building teams from early stage to category leadership.
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
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.
Kelli Paull
VP of Customer Success
Customer success leader with more than a decade in B2B SaaS, most recently Vice President of Customer Experience at Outbound AI and previously Vice President of Customer Success at Shyft, a workforce technology company serving Fortune 500 employers.
Kelli Paull
VP of Customer Success
Customer success leader with more than a decade in B2B SaaS, most recently Vice President of Customer Experience at Outbound AI and previously Vice President of Customer Success at Shyft, a workforce technology company serving Fortune 500 employers.
Jeremy Leon
VP 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
VP 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
VP 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
VP 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.
Tom Cox
VP of Commercial Partnerships
Benefits administration technology veteran with over two decades architecting and scaling channel sales programs, holding leadership roles at WEX Health and Alegeus before joining When to build partnerships with TPAs, health plans, and COBRA administrators.
Tom Cox
VP of Commercial Partnerships
Benefits administration technology veteran with over two decades architecting and scaling channel sales programs, holding leadership roles at WEX Health and Alegeus before joining When to build partnerships with TPAs, health plans, and COBRA administrators.
News & Insights
Read the latest product updates, company news and industry insight.
