Senior Engineer

The Opportunity

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.

The Role

When is looking to add a Senior Engineer to our team. When is the AI workforce transitions platform for employers — we turn workforce change into savings by lowering high-cost medical claims, reducing COBRA liability, and protecting employer brand by giving departing employees an excellent benefits-transition experience. You'll build across our full stack: the HR-facing tools that let employers manage the entire offboarding process, and the post-employment portal where departing employees navigate an AI-driven health insurance marketplace during one of the hardest moments in their working lives.

This is a generalist, full-stack role for an engineer who can own a problem end to end — from the stakeholder conversation to the data model to the shipped interface. Because AI tooling like Claude Code lets our team ship at a rapid pace, you'll work directly with the stakeholders you're solving for and take on work traditionally owned by product: understanding the problem, shaping the solution, and defining what “done” looks like. That direct line is the point — it removes the hand-offs that slow teams down and gives you an outsized impact on the people you partner with. You'll work closely with the CTO to set the technical foundation the rest of the team builds on, and you'll bring your passion for AI and your desire to build a compassionate platform for those impacted by job loss.

What You'll Do

• Ship features across the stack. Plan, design, and implement product features end to end, working closely with product to develop the right solution.

• Partner directly with stakeholders. Work shoulder-to-shoulder with the teams you're building for — member services, operations, and beyond — to turn ambiguous problems into shipped solutions, without waiting for a full spec to be handed down.

• Own the product thinking. Scope work, weigh tradeoffs, and decide what to build — not just how to build it. Your speed with AI tooling means you'll often carry a problem from idea to launch yourself.

• Build with AI. Integrate LLM-driven experiences, agents, and reusable skills into the platform — not as bolt-ons, but as core parts of how the product works.

• Move fast with modern tooling. Use AI development tools like Claude Code to prototype and ship quickly without sacrificing quality.

• Keep the codebase healthy. Write clean, testable, maintainable code and perform thoughtful code reviews for the rest of the team.

• Make your work observable. Instrument what you build so we can see how users engage with it, where they struggle, and how our member services team can support them.

• Communicate and coordinate. Clearly communicate implementation requirements to the team and help manage day-to-day work through our agile process.

Tech Stack

• Frontend: React, TypeScript, MaterialUI, GraphQL

• Backend: Node.js, TypeScript, Firebase Functions, Apollo GraphQL, Firestore • AI: LangGraph, LangSmith, Claude / LLM APIs, agent & skill development, Claude Code

• Ops: GCP (Firebase hosting, Firestore, pub/sub, serverless functions, load balancers, BigQuery), GitLab, JIRA, Notion, Apollo Studio, Cypress.io http://Cypress.io, Jest

What We'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

• The instinct to think past “does it work?” to “will it scale, and can we see how it's used?” • Strong problem-solving and communication skills

• Passion for fixing the broken offboarding system and helping people through their job transitions

Nice to Have

• Experience in health insurance, benefits, or a regulated healthcare / fintech domain — enough to understand the tools we're building and the compliance constraints (PHI / PII, HIPAA) that shape them

• Familiarity with data analytics and product instrumentation

• Experience laying technical foundations on a small, fast-moving team