Lead AI Designer with Retirement & Wealth Domain expin Boston, MA or Windsor, CT

Role: Lead AI Designer with Retirement & Wealth Domain exp

Location: Boston, MA or Windsor, CT (onsite role)

Duration: Long Term

Responsibilities

• AI EXPERIENCE DESIGN & INTERACTION PATTERNS
• AI-NATIVE PROTOTYPING & DESIGN TOOLING
• PARTICIPANT & ADVISOR RESEARCH
• DESIGN SYSTEM & ACCESSIBILITY
• POD COLLABORATION & PRODUCT INFLUENCE

Experience

• 8+ years of product design experience with at least 3 years designing AI-powered features in production consumer or professional-facing applications — not just design concepts but shipped AI experiences with real users.

• Demonstrated experience at Lead or Staff Designer level: defining design patterns used by others, contributing to product strategy, and setting the design quality standard for a product area rather than executing within one already defined.

• Experience in financial services, fintech, or a regulated consumer product environment where compliance requirements shape design decisions in the same artifacts as user experience decisions.

• Portfolio demonstrating AI experience design specifically: conversational interfaces, AI recommendation surfaces, uncertainty and error states, human-in-the-loop design patterns, and explainability UI — not just general product design work.

Design Skills — Required

• Figma (expert level): component-based design, auto-layout, variant systems, prototyping, and the design system contribution workflow — at the level where the Lead AI Designer is extending and maintaining the component library, not just consuming it.

• Interaction design for AI: proven ability to design for non-deterministic, probabilistic outputs; experience designing streaming text interfaces, confidence indicators, correction affordances, and AI attribution patterns in production products.

• Conversational and agentic UI design: experience designing chat interfaces, voice interaction flows, or multi-step AI-guided task completion — with specific attention to how the design handles LLM response latency, variability, and failure.

• Prototyping for AI: experience using Protopie, Voiceflow, or equivalent tools to prototype AI interaction patterns; ability to build lightweight front-end prototypes for research using AI coding tools.

• User research: ability to design, recruit for, moderate, and synthesize qualitative research sessions specifically about AI trust, transparency, and comprehension; experience with usability testing of AI features, not just static interfaces.

• Accessibility engineering: WCAG 2.2 AA compliance in practice, with specific experience designing for the accessibility challenges of AI-generated and dynamically updated content; familiarity with screen reader behavior for conversational and streaming UI patterns.

• Design systems: experience contributing to and maintaining a shared component library at scale; ability to document patterns in a form that other designers and engineers can implement consistently.

AI Tooling — Required

• AI-assisted design workflow in daily practice: generative AI tools for ideation and asset exploration, LLM-assisted copy drafting for UI text and disclosure language, and AI-powered design analysis — not as experiments but as standard working tools.

• Prompt engineering familiarity: sufficient understanding of how LLM prompts shape outputs to contribute meaningfully to the prompt refinement process alongside the Lead AI Engineer — specifically for the copy, format, and disclosure requirements that are design decisions.

• AI coding tools for prototyping: Claude Code, GitHub Copilot, Cursor, or equivalent; ability to build a lightweight React/TypeScript front-end prototype for research purposes without requiring engineering support.

• Fluency in AI system concepts: understanding of RAG retrieval, streaming inference, confidence scoring, agent tool use, and model output variability at the level required to design for them — not to build them, but to anticipate their design implications accurately