Lead AI Engineer

Lead AI Engineer

Lead AI Engineer

When is a US-based, venture-backed company that has built a novel AI-driven health insurance marketplace and post-employment platform. Our product will transform how companies offboard employees and how people manage their transition between jobs.

We are seeking a dynamic, proven AI engineer to join our team as a Lead AI Engineer. Reporting directly to the CTO, this newly created role offers significant visibility and influence across the organization.

The ideal candidate has deep expertise in AI/ML engineering and architecture within the HR, benefits, or HR technology sectors, with a strong track record of designing and delivering innovative, high-impact AI solutions.

This engineer will be responsible for shaping and executing our AI development strategy, driving the design and deployment of intelligent systems that power our core product, and pushing the boundaries of what's possible with AI in our space. The role will also partner closely with the executive and product teams to align AI innovation with our product, sales, and business strategy to accelerate growth.

• Own the end-to-end architecture of When’s AI systems—from LLM orchestration and agent frameworks to data pipelines, model serving, and observability
• Design scalable, maintainable infrastructure that supports rapid experimentation without sacrificing reliability—thinking through failure modes, fallback strategies, and system-wide impact before building
• Build and maintain the data layer that captures how AI features are used: structured logging, event pipelines, and integration with analytics and reporting tools
• Future-proof our AI stack so new models, capabilities, and partner integrations can be adopted without re-architecture

• Lead the design and development of AI-driven features embedded in the product - conversational assistants that guide users through COBRA elections, ACA marketplace enrollment, 401k rollover, and benefits decisions
• Build systems that serve both our end users and our member services team—ensuring internal teams can track how users interact with AI tools, identify where users struggle, and intervene when needed
• Design AI interaction patterns that build trust: streaming responses, confidence indicators, graceful degradation, and human-in-the-loop escalation paths
• Collaborate with the UX team to translate AI capabilities into intuitive interfaces that drive measurable user outcomes

• Instrument AI features with structured tracking that answers business questions:
  How are users engaging? Where do they drop off? What drives conversion? Where does the AI add value vs. create friction?
• Build reporting infrastructure that gives Product, Member Services, and leadership visibility into AI performance—usage patterns, sentiment, resolution rates, and ROI
• Design and run experiments (A/B tests, prompt variations, workflow comparisons) with proper measurement frameworks to continuously optimize AI-driven experiences
• Partner with Product and Data teams to define the metrics that matter and build the feedback loops that make them actionable

• Work directly with the CTO to develop and execute When’s AI strategy—evaluating new models, tools, and approaches with a critical eye on business impact and scalability
• Bring a systems mindset to every decision: how does this feature affect our data model? What downstream dependencies does it create? How will we maintain it at 10x scale?
• Serve as the AI technical authority across the engineering org—providing guidance on best practices, code reviews, and architectural decisions
• Contribute to hiring and team development as When’s AI capabilities grow

• 5+ years of experience in software engineering with at least 2–3 years focused on AI/ML systems, LLM integration, or intelligent product features in production environments
• Proven track record building AI systems at scale—not just prototyping, but shipping, instrumenting, and maintaining production AI infrastructure
• Strong systems thinking: you…