Senior Learning Designer, Math at Outsmart

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 You'll work with a highly talented and collaborative team to develop Outsmart's math learning experience from curriculum architecture through content creation, assessment design, and learner feedback loops. You'll work closely with product managers, engineers, and fellow learning designers to build rigorous, engaging, and scalable math courses that bring joy back to learning. As an AI-native company, you'll also shape how AI tools and data insights are woven into curriculum development, content generation, and continuous improvement. Who You Are - Advanced degree in Mathematics, Applied Mathematics, or Math Education. - 3+ years designing college-level mathematics curriculum (online or hybrid experience a plus) - Deep pedagogical content knowledge across the math sequence — algebra through calculus, statistics, and beyond - Proven experience building technology-enabled learning experiences in collaboration with product and engineering teams - Fluency with education technology and AI-assisted content workflows - Familiarity with learning standards and frameworks (e.g., CCSS, NCTM practices, mastery-based progression) - Strong communicator who can translate pedagogical rationale for non-technical audiences - Bonus: experience with adaptive learning systems, A/B testing educational content, or app-based course design What You’ll Work On - Math curriculum end-to-end — course architecture, learning outcomes, sequencing, and mastery-based progression from intro through advanced - Assessment strategy — formative and summative assessments that accurately measure mathematical proficiency and inform course iteration - Interactive content and tooling - AI-assisted content pipelines - Data-informed iteration — interpreting qualitative and quantitative learner data to identify gaps, improve engagement, and drive efficacy - Cross-functional collaboration — working with Product, Engineering, and Learning Design to ship technology-enabled math experiences on schedule What Helps You Succeed - You thrive in ambiguity and are energized by building from scratch - You balance academic rigor with startup pragmatism — you know when to ship and iterate - You think like a product builder, not just a subject-matter expert — you care about the learner experience at every click - You take ownership without being asked and surface risks early - You're excited about AI's role in education and know where human judgment is non-negotiable - You care deeply about access and the students behind every learning outcome Salary Range: $100K–$170K Perks - Competitive salary and equity - Healthcare for you and your dependents (medical, dental, and vision) - Parental leave for any full-time employee who has been with us for at least 6 months (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.