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Staff Product Designer, AI

Contentsquare - Pittsburgh, PA, United States - Hybrid - posted 2026-10-22

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Contentsquare is a global leader in experience analytics, serving 3,000+ enterprise and mid-market brands. The company has raised $1.4bn and is rated a Leader by G2 across ten enterprise categories. Sense is Contentsquare's agentic AI layer, built on ten years of cross-customer behavioral data, featuring an AI analyst, chat and visual-stories interface, and a memory and object model. This role leads design for Sense's core AI surfaces as a standalone product. You will own the complete design lifecycle—from problem framing through shipped detail—for Sense Analyst, the object model, and inline visualizations. This is not a feature role; you will own strategy and vision, shape the roadmap alongside Product Management, and define design patterns for surfaces that largely have no existing reference patterns. Key responsibilities include: - Own design for Sense Analyst, the object model, and inline visualizations from conception to shipped detail - Lead experience strategy and vision for this product surface; shape roadmap with Product Management - Work from the data model up: define persistent objects, how memory and context carry across sessions, and how these surface to users - Set quality bars for AI-generated output: define what "trustworthy" and "good" look like, and how output gets versioned and evaluated with engineering - Partner with engineering on customer-facing agentic workflows and AI-generated output versioning and trust mechanisms - Collaborate with other designers building AI-native product parts: review work, push thinking, and mentor less-senior designers in this emerging space Requirements: - Staff-level product design experience, primarily in B2B SaaS, ideally in analytics or workflow tools where users make decisions from complex information - Hands-on design experience shipping AI or agentic features: chat interfaces, generative output, memory/personalization, human-AI trust patterns - Ability to reason about the data model underlying an interface - Extensive track record shipping zero-to-one work in ambiguous problem spaces with clear connection to business outcomes, not just user outcomes - Strong collaboration and facilitation skills; ability to bring engineering, PM, and other designers to shared decisions - Leadership and influence - Experience designing for LLM and AI experiences, including prompt engineering Nice to have: - Experience designing for enterprise or executive personas - Prototyping in code to test interaction models before build - Background in analytics, attribution, or behavioral data products

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