Principal Product Designer

Outsmart is a mission-driven, early-stage startup reimagining higher education for the age of AI by creating an entirely new collegiate experience that expands access and opportunity. Backed by $38M from top venture firms including Khosla Ventures, Forerunner, DST Global Partners, and Lightspeed, the company is led by former Duolingo executives and a founding team that also includes Emmy Award winners. With a strong culture centered around high-impact, detail-oriented team members, Outsmart is already seeing significant traction, generating 1–5 million weekly organic views on social media.

As a Principal Product Designer at Outsmart, you’ll help shape an entirely new kind of college experience from the ground up. You’ll lead design for major areas of the product, working closely with Product, Engineering, and leadership to turn complex problems into simple, intuitive, and delightful experiences for students.

This is a hands-on leadership role. You’ll spend most of your time designing, prototyping, and shipping, while also helping guide other designers, raise the quality bar, and evolve how the design team works as Outsmart grows.

• Experienced product designer and design leader who has shipped exceptional consumer products and managed other designers

• Combines strong product thinking with excellent visual and interaction design skills

• Comfortable moving between big-picture product strategy and the smallest details of an interaction

• Gives clear, constructive feedback, develops designers, and creates an environment where great work can happen

• Comfortable with ambiguity, moves quickly, and brings structure to problems without adding unnecessary process

• Genuinely curious about AI, actively using new tools to prototype, explore, and rethink how products and design teams can work

• Lead end-to-end design for major areas of the Outsmart student experience

• Turn ambiguous product problems into clear strategies, flows, prototypes, and polished experiences

• Partner closely with Product and Engineering from early exploration through launch and iteration

• Mentor and manage designers, helping them grow while raising the quality of their work

• Lead critiques and create a culture of thoughtful, direct, and productive feedback

• Help establish design processes that allow a small team to move quickly and maintain a high quality bar

• Use research, data, experimentation, and rapid prototyping to inform product decisions

• Evolve Outsmart’s design system and overall product language

• Help grow the design team and shape its culture as the company scales

• 8+ years of product design experience, with significant experience designing consumer-facing digital products

• Previous experience managing and developing product designers

• A portfolio demonstrating exceptional product thinking, interaction design, and visual craft

• Experience owning complex products or major product areas from strategy through launch

• A strong track record of shipping products used by real customers at meaningful scale

• Excellent Figma and prototyping skills, with a willingness to stay deeply hands-on

• Strong collaboration with Product and Engineering, including comfort navigating technical and business constraints

• Experience using AI tools to accelerate design, prototyping, and exploration

• Strong communication skills and the ability to influence product direction across disciplines

• High standards for craft paired with the judgment to know when to ship and iterate

• A low-ego approach to leadership, collaboration, critique, and feedback

• Bonus: experience with consumer education, social, gaming, or other highly engaging products