Senior Engineer

About the role

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.