Lead Product Designer

Sixfold•New York, NY

2d•$165,000 - $180,000•Hybrid

About The Position

We’re looking for a Lead Product Designer to own design for our flagship Property & Casualty underwriting AI product. This role is ideal for a senior, generalist designer who thrives in a highly collaborative environment and enjoys tackling complex problems in enterprise AI software. You’ll partner with PMs, developers, and AI engineers as a peer—shaping an experience that blends agent automation with the nuanced judgment of underwriters, and defining how our agents reason, act, fail, and hand off to humans. This role reports to our Head of Design and is a senior IC position with mentorship responsibilities, with meaningful influence on our design patterns, process, and culture.

Requirements

7+ years of experience as a product designer with a proven track record in enterprise software. A portfolio demonstrating outcomes fully delivered into production.
AI fluency: You can engage with engineers on agentic architectures, HITL patterns, and failure modes as a peer—not just as someone who designs the UI layer on top. You understand how agents reason and where humans need to intervene.
Systems-first thinking: You design the logic before the screen. You map agent flows, confidence thresholds, and handoff moments before opening Figma.
Tinkerer mentality: When you see an inefficiency, you build something to fix it. You prototype with AI tools, use agentic coding to ship small changes, and experiment because you're genuinely curious.
Strong facilitator: You lead productive conversations through ambiguity, align cross-functional teams on hard tradeoffs, and don't wait for someone else to call the meeting.
Strong research craft: You can plan and run user research (from recruiting through synthesis) and translate findings into product decisions and shipped outcomes.
Context switching with systems-level clarity: You can juggle a diverse set of projects, quickly build context, and connect the dots at a higher level so day-to-day decisions align with the broader product direction.
Generalist range: Experience across the design process, from user research to visual design to content.
Specialized depth in at least one: UX writing/content design, user research, visual design human-in-the-loop AI systems, or API design.

Nice To Haves

Enterprise SaaS / Insurtech experience (preferred): Familiarity with designing for complex, data-driven workflows. Even better if you've worked in insurance before.

Responsibilities

Own the end-to-end design direction for our P&C underwriting product—from discovery through implementation and iteration.
Drive product strategy alongside PMs by framing problems, running discovery, and bringing back recommendations that shape the roadmap.
Design agentic workflows and human-in-the-loop interactions—defining how AI agents plan, execute, fail, and hand off to underwriters.
Engage directly with AI engineers on how agent behavior maps to user intent.
Use agentic coding tools like claude codea to push quick design changes and refinements directly to the product.
Lead alignment conversations and facilitate through ambiguity—even when you're not the subject matter expert in the room.
Mentor designers on the team and raise the design bar across your product area.
Jam with the design team on new designs, the design system, agentic prototyping, and anything else that enables Sixfold designers to excel.
Drive continuous discovery with underwriters and customer teams—running interviews, concept tests, and usability studies to pressure-test direction.
Synthesize research into crisp insights and recommendations that shape roadmap, agent behavior, and workflow design.
Help our customers smoothly transition to the world of enterprise AI agents.