Staff Product Designer, AI

Contentsquare; Pittsburgh (Allegheny County); Hybrid; USD 120,000 - 190,000; Full time

Benefits offered by this job

Stock options

Hybrid/remote work policy

Generous paid time off

Lifestyle allowance

Employee Resource Groups

Job summary

Contentsquare seeks a Staff-level Product Designer to lead Sense Analyst design, owning the object model and inline visualisations end-to-end. You will shape the experience strategy and roadmap with Product Management, starting from the data model and extending to cross-session memory and context.

You’ll define the trust and quality standards for AI outputs, collaborating with engineers and other designers.

Qualifications

• Staff-level product design experience in B2B SaaS, preferably analytics or workflow tools.
• Hands-on design experience shipping AI or agentic features such as chat interfaces and memory.
• Ability to reason about the data model underneath an interface.
• Track record of shipping zero-to-one work in ambiguous spaces with business impact.
• Strong collaboration and facilitation skills across engineering, PM, and design.
• Experience designing for LLM/AI experiences, including prompt engineering.

Responsibilities

• Own design for Sense Analyst, the object model, and inline visualisations from framing to shipped detail.
• Lead experience strategy and vision for this product surface and shape its roadmap with PMs.
• Work from the data model up: memory, context, and persistence across sessions.
• Set quality bar for AI-generated output and versioning with engineering.
• Partner with engineering on customer-facing agentic workflows and trust.
• Collaborate with other designers on AI-native parts of the product and coach junior designers.

Skills

Staff-level product design

AI/LLM design

Collaboration & facilitation

Leadership

B2B SaaS experience

Data-model reasoning

Job description

Contentsquare is the all-in-one experience intelligence platform designed to be easily used by anyone who cares about digital journeys. With our flexible and scalable platform, organizations quickly get a deep understanding of their customers’ whole online journey.

We are a global leader in the experience analytics space, with a growing presence across 15 offices worldwide. We’re here to stay—and we’re looking for team members who are excited to drive impact and help us scale even further.

Our aim is to create an inclusive workplace where everyone learns and succeeds. Contentsquare has built a community of individuals who are daring, understanding, and deliberate. We invite you to join us in making the complex simpler—for our customers, their customers, and each other.

Important note: Be careful of scammers pretending to be from Contentsquare. We will never ask for money or contact you through random texts. Any communication from our in house Talent Acquisition team will only ever come from our contentsquare.com or @contentsquare-ext.com domain. For more information, visit our careers blog.

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.

Why you should join Contentsquare

We invest in our people through career development, mentorship, social events, philanthropic activities, and competitive benefits. We are always assessing the perks we offer to ensure we’re aligned with the employees’ needs.

Here are a few we want to highlight:

• - Virtual onboarding, Hackathon, and various opportunities to interact with your team and global colleagues both on and offsite each year
• - Work flexibility: hybrid and remote work policies
• - Generous paid time‑off policy (every location is different)
• - Lifestyle allowance
• - A Culture Crew in every country we’re based in to coordinate regular activities for employees to get to know each other and bond outside of work
• - Every full‑time employee receives stock options, allowing them to share in the company’s success
• - We have multiple Employee Resource Groups, that offer a safe space for individuals who share common identities, life experiences, or allyship to connect, support one another, and passionately advocate for the issues close to their hearts
• - And more benefits tailored to each country

Contentsquare is an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to sex, gender identity or expression, sexual orientation, race, color, religion, national origin, disability, protected veteran status, age, or any other characteristic protected by law.

Your personal data is used by Contentsquare for recruitment purposes only. Read our Job Candidate Privacy Notice to find out more about data protection at Contentsquare and your rights. You can exercise your rights by using our dedicated Data Subject Rights Portal here.

Your personal data will be securely stored in our hosting provider’s data center in Oregon (US west). We have implemented appropriate transfer mechanisms under applicable data protection laws.

Contentsquare may use AI‑assisted tools to help review and screen applications. All decisions involving hiring are made by human reviewers, and your personal data will be processed in accordance with our Candidate Privacy Policy.