Senior Engineer

When; United States; On-site; USD 130,000 - 160,000; Full time

Job summary

When is seeking a Senior Engineer to join our AI-driven workforce transitions platform. You will build the HR-facing tools and the post-employment portal, enabling employers to manage offboarding and departing employees navigating an AI-powered health insurance marketplace.

You’ll ship features end-to-end, collaborate with stakeholders, and apply AI tooling to create scalable, observable systems while maintaining high-quality code in an agile setting.

Qualifications

• 5+ years building and planning product features as a full-stack engineer.
• Strong command of React, TypeScript, GraphQL, Node stack and related tools.
• Proven ability to collaborate cross-functionally with non-technical stakeholders.
• Ability to define scope, tradeoffs, and what constitutes done beyond a spec.
• Hands-on experience using AI development tools (Claude Code, Cursor, Windsurf).
• Experience building with LLMs—agents, skills, prompts, and integration points.

Responsibilities

• Ship features across the stack end-to-end with product teams.
• Partner with stakeholders to turn ambiguous problems into shipped solutions.
• Own product thinking: scope work, weigh tradeoffs, decide what to build.
• Build with AI: integrate LLM-driven experiences into the platform.
• Move fast with modern tooling and prototype using AI development tools.
• Keep the codebase healthy with clean, testable code and reviews.
• Make work observable by instrumenting features to monitor usage.
• Communicate requirements clearly and manage day-to-day work in agile processes.

Skills

Full-stack engineer

React

TypeScript

GraphQL

AI tooling

Cross-functional collaboration

Product sense

LLM integration

Code reviews

Tools

GitLab

JIRA

Notion

Apollo Studio

Claude Code

LangGraph

LangSmith

Job description

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.

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.

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.

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, 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

Compensation Range: $130K - $160K