Principal Product Designer

The Role

We're building a deeply AI-enabled product that will give every college student an unfair advantage in the moments that matter most. The audience is massive. Every undergraduate in the country is a potential user, and this product is being built from the ground up to establish product-market fit at that scale.

It is the single most transformative initiative in the company: zero-to-one, live in market, and moving fast. We're looking for the person who will own the design and product strategy.

This is not a traditional product design role. We need someone who operates at the intersection of product strategy, design craft, and AI-first delivery: a person who can determine which problems are worth solving, turn that into a plan the team can build, and bring it to life through design, rapid prototyping, and real user testing. You'll own the full loop, from student insight to shipped experience.

You will report directly to the Chief Product Officer.

What you'll do

Strategy & product direction

• Use quantitative and qualitative data to deeply understand the way students are using our products, and to find opportunities for improvement
• Use a variety of techniques (one-on-one user interviews, rapid prototypes built with AI coding tools, and whatever else works) to validate and invalidate a wide breadth of ideas quickly and cheaply
• Be an influential storyteller. Help people understand why you've chosen what to build next, with evidence, while staying genuinely open to their input and incorporating it to improve on your plans

Design craft & quality

• Build the design language system (components, patterns, and tokens) that lets our AI coding tools (Claude and others) produce excellent software at speed
• Set the bar for design quality and help your teammates understand why it matters. Design is something we all care about here, and everyone's work should reflect that
• Audit what ships against what was designed, so the promise of quality always lands for the end user

Delivery & engineering partnership

• Work closely with engineering, adapting the product as we learn what's technically feasible, where the real constraints are, and where the opportunities lie; you're responsible for the end experience, not just the spec
• Drive the pace and improve the process as we go, always looking for ways the team can work better as a whole. Warp speed is your comfort zone, and you're allergic to inefficiency
• You have a strong bias toward shipping, and the judgment to know when to hold

Required Qualifications

• 10+ years of experience, comfortable in both product strategy and product design at Senior IC caliber in each; credible in a Staff PM or Staff Designer role at any top-tier product company
• A portfolio that demonstrates both strategic thinking (why we built this, what tradeoffs we made) and strong visual and interaction design craft
• Experience owning product direction and making roadmap decisions
• Experience building 01 products; you're energized by ambiguity, not paralyzed by it
• Fluency with a design tool (Figma or similar): you can go from idea to polished design quickly
• Fluency with vibe coding tools: you can prototype working software yourself, fast
• Comfort with data: you know how to read a funnel, interpret an A/B test, and use quantitative signals alongside qualitative research
• Collaborative by nature: you'd rather ship something great with a team than build alone
• An excellent designer and builder who genuinely loves solving problems for users
• Willing to stand behind your decisions and change your mind when the evidence demands it
• A track record of shipping consumer products that moved business metrics, not just products that shipped

Preferred Qualifications

• Experience with AI or agent-based products: you understand the design challenges of proactive, AI-driven UX
• Experience designing consumer products used by millions
• Experience in fast-moving or early-stage environments

How we work

We've refactored our product development lifecycle for the age of AI. The way we validate ideas, build prototypes, and ship software is meaningfully different from how most teams still work: tighter loops, no unnecessary ceremonies or documentation (just enou

Skills

A/B Testing, Artificial Intelligence (AI), Documentation, Integrated Circuit (IC) Design, Metrics, Problem Solving Skills, Process Improvement, Product Design, Product Development, Product Lifecycle, Product Shipments, Product Strategy, Qualitative Research, Rapid Prototyping, Refactoring, Resolve Customer Issues, Software Prototyping, Strategic Planning, Team Player, User Interface Design, User Interface/Experience (UI/UX)

About the Company

Chegg, Inc.