Principal Product Designer

Job Description

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.

• 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

• 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

• 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

• 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 0→1 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

• 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

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 enough to move things forward), and AI doing more of the heavy lifting on code and coordination. If that’s already how you want to work, this role is for you.

The role is hybrid. We don’t require daily in-office presence, but you should be local to either Austin, the Bay Area, or Chicago and be available for in-person collaboration during key sprints, design reviews, and customer sessions. Some weeks will be heads-down-in-the-office weeks, and a small amount of travel will be expected.

You’ll report directly to the CPO, who is one of your closest collaborators along with a technical lead. Most of your time goes to the craft: designing, prototyping, testing with students, and building with the team. You’ll be highly self-directed; no one will be managing your calendar or telling you what to work on each morning. Success will be judged by the quality of the products we build.

The base salary pay range for this position is $180,000 to $285,000.  Although this range represents the full range for the position, the actual pay will vary within this range based on geographic location, job type, professional experience, and other factors.  
In addition, Chegg offers a comprehensive benefits plan for eligible employees, including medical, dental, vision, life and supplemental life insurance, short-and long-term disability, mental health support, parental leave, paid time off, paid holidays, 401(k) with matching contributions, Flexible Spending Account (FSA) and Health Savings Account (H.S.A.) options, an Employee Stock Purchase Plan, and other benefits found at: https://www.chegg.com/about/working-at-chegg/benefits/.

Why do we exist?

Students are working harder than ever before to stabilize their future. Our recent research study called State of the Student shows that nearly 3 out of 4 students are working to support themselves through college and 1 in 3 students feel pressure to spend more than they can afford. We founded our business on provided affordable textbook rental options to address these issues. Since then, we’ve expanded our offerings to supplement many facets of higher educational learning through Chegg Study, Chegg Math, Chegg Writing, Chegg Internships, Chegg Skills, and more to support students beyond their college experience. These offerings lower financial concerns for students by modernizing their learning experience. We exist so students everywhere have a smarter, faster, more affordable way to student.

Life at Chegg: http://youtu.be/Fwf90zgaOLA

Chegg Corporate Career Page: https://jobs.chegg.com/

Chegg India: http://www.cheggindia.com/

Chegg Israel: http://www.chegg.com/about/working-at-chegg/israel/

Chegg Skills:  https://www.chegg.com/skills

 
Chegg out our culture and benefits!

http://www.chegg.com/about/working-at-chegg/benefits/

Chegg is an equal opportunity employer