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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.
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