When Insurance is a technology platform that helps individuals and employers navigate health insurance options during transitions such as job loss or retirement. Backed by Purple Arch Ventures.
About the role
Every year, tens of millions of Americans go through a coverage transition: a layoff, a resignation, a move into retirement, a 65th birthday while still working. It is one of the most consequential financial decisions a person makes, and it usually arrives as a twenty-page packet during the worst week of their professional life. Nobody owns it. COBRA makes the event compliant; it does not make it managed. That gap is expensive for employers and genuinely hard on people.
What they're looking for
- • 5+ years building and planning product features as a full-stack engineer
- • Strong command of our stack — or the range to get there quickly (React / TypeScript / GraphQL / Node)
- • Strong cross-functional collaboration — you're comfortable working directly with non-technical stakeholders and turning a loosely-defined problem into a shipped solution
- • Product sense: the judgment to make scope and tradeoff decisions and define what “done” looks like, not just execute against a spec
- • Hands-on experience using AI development tools (Claude Code, Cursor, Windsurf, or similar) as part of your daily workflow
- • A working understanding of how to build with LLMs — agents, skills, prompt design, and the judgment for where each approach fits
More about this role
Every year, tens of millions of Americans go through a coverage transition: a layoff, a resignation, a move into retirement, a 65th birthday while still working. It is one of the most consequential financial decisions a person makes, and it usually arrives as a twenty-page packet during the worst week of their professional life. Nobody owns it. COBRA makes the event compliant; it does not make it managed. That gap is expensive for employers and genuinely hard on people.
When is the enterprise platform for guided health insurance decisions at every qualifying life event. Through When Choice, When Medicare, and When ICHRA, we combine an intelligent decision-support experience with licensed, non-commissioned agents so every person understands their real options and lands somewhere good. We have supported more than one million employees and managed over 204,000 qualifying events for Fortune 50 and Fortune 500 employers, reducing COBRA enrollment by up to 80% while improving the experience for the people leaving. Doing right by employees and taking cost out are usually opposing forces. Here they are the same action.
When is looking to add a Senior Engineer to our team. When is the AI...
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