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Contentsquare

Remote · North America

Staff Product Designer, AI

Prototyping Lead / Staff Full-time Remote
Who can apply
United States
Employment
Full-time
Posted
How to apply
On Contentsquare’s own site
At Contentsquare
3 live remote roles
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About the role

Contentsquare works with 3,000+ enterprise and mid-market brands on data from 1.3 million websites. We've raised $1.4bn to build the platform, and G2 rates us a Leader across ten enterprise categories. Sense is our agentic layer on top of that: ten years of cross-customer behavioural data, an AI analyst, a chat and visual-stories interface, and a memory and object model underneath both.

This role leads design for Sense's core AI surfaces as a product in its own right, not a feature downstream of someone else's roadmap. That means owning strategy and vision for this surface, not just shipping against a brief. Most of what you're designing here has no reference pattern to draw from yet; part of the job is defining and sharing these patterns.

What you'll do

  • Own design for Sense Analyst, the object model, and the inline visualisations it returns, from problem framing through to shipped detail.

  • Lead the experience strategy and vision for this product surface, and shape its roadmap alongside Product Management.

  • Work from the data model up: what counts as a persistent object, how memory and context carry across sessions, and how that surfaces to the person using it.

  • Set the quality bar for AI-generated output on these surfaces: what "trustworthy" and "good" look like, and how that gets versioned and evaluated with engineering.

  • Partner with engineering on customer facing agentic workflows and how AI-generated output gets versioned and trusted.

  • Work alongside the other designers building the AI-native parts of the product: review each other's work, push each other's thinking, and help less-senior designers on the team build judgement in this space.

What You'll Bring

  • Staff-level product design experience, most of it in B2B SaaS, ideally analytics or workflow tools where users make decisions from complex information.

  • Hands-on design experience shipping AI or agentic features yourself: chat interfaces, generative output, memory or personalization, human-AI trust patterns.

  • Ability to reason about the data model underneath an interface

  • An extensive track record of shipping zero-to-one work in ambiguous problem spaces, with a clear line from that work to business outcomes, not just user outcomes.

  • Strong collaboration and facilitation skills :you can bring engineering, PM, and other designers to a shared decision, not just present finished work.

  • Leadership and influence.

  • Experience designing for LLM and AI experiences, including prompt engineering.

    • Nice to have:

  • Designing for enterprise or executive personas.

  • Prototyping in code to test an interaction model before it's built.

  • A background in analytics, attribution, or behavioural data products.

Skills

Prototyping LLM

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