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.
What You’ll Be Doing
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.
Who You Are
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
What You’ll Own
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
What Helps You Succeed
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
Salary Range: $175,000–$225,000.
Perks
Competitive salary, equity, and benefits
Healthcare for you and your dependents (medical, dental, and vision)
Parental leave for any full-time employee (birthing, non-birthing, and adoptive parents)
15 PTO days per year, a winter break, and 12+ paid company holidays per year
Remote work days
Lunch provided in-office daily
Working with super talented people who want to make a difference in the world
Outsmart is committed to building an equitable and inclusive workplace and is proud to be an equal opportunity employer. We consider all qualified applicants for employment regardless of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, disability, age, veteran status, or any other characteristic protected by applicable law.