Staff Product Designer, AI

Contentsquare•Pittsburgh, PA

About The Position

Contentsquare is hiring a Staff Product Designer to lead design for Sense’s core AI surfaces as a product in its own right. Sense is an agentic layer built on Contentsquare’s cross-customer behavioural data, including an AI analyst, chat and visual-stories interface, and an underlying memory and object model. The role owns the experience strategy and vision for this product surface and shapes its roadmap alongside Product Management. Much of the work has no established reference pattern, so the designer will help define and share new patterns. The designer will own Sense Analyst, its object model, and the inline visualisations it returns, from problem framing through shipped detail. The role involves deciding what constitutes a persistent object, how memory and context carry across sessions, and how they appear to users. The designer will establish quality standards for AI-generated output and partner with engineering to version and evaluate it, while collaborating with other designers and helping less-senior team members develop judgement in this area. Contentsquare describes itself as a global experience analytics leader with a presence across 15 offices and more than 3,000 enterprise and mid-market brand customers. The company offers hybrid and remote work policies, a generous paid time-off policy that varies by location, lifestyle allowance, and stock options for full-time employees. Additional benefits vary by country.

Requirements

Staff-level product design experience, mostly in B2B SaaS; analytics or workflow tools involving complex information are ideal.
Hands-on experience shipping AI or agentic features, such as chat interfaces, generative output, memory or personalization, and 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 a clear connection to business outcomes.
Strong collaboration and facilitation skills, including bringing engineering, Product Management, and designers to shared decisions.
Leadership and influence.
Experience designing LLM and AI experiences, including prompt engineering.

Nice To Haves

Experience designing for enterprise or executive personas.
Prototyping in code to test an interaction model before it is built.
Background in analytics, attribution, or behavioural data products.

Responsibilities

Own design for Sense Analyst, the object model, and the inline visualisations it returns, from problem framing through shipped detail.
Lead the experience strategy and vision for the product surface and shape its roadmap alongside Product Management.
Define persistent objects, how memory and context carry across sessions, and how these are presented to users.
Set quality standards for AI-generated output and work with engineering to version and evaluate it.
Partner with engineering on customer-facing agentic workflows and how AI-generated output is versioned and trusted.
Collaborate with other designers working on AI-native product areas, review work, challenge ideas, and help less-senior designers build judgement in this space.

Benefits

Career development and mentorship.
Social events and philanthropic activities.
Competitive benefits.
Virtual onboarding, a hackathon, and opportunities to interact with teammates and global colleagues on- and offsite.
Hybrid and remote work policies.
Generous paid time off; policy varies by location.
Lifestyle allowance.
Country-based Culture Crews that coordinate employee activities.
Stock options for every full-time employee.
Employee Resource Groups.
Additional benefits tailored to each country.