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

In this role, you’ll be at the forefront of the AI that powers Outsmart’s applications. As an early member of the engineering team you’ll play a critical role in setting the tone for Outsmart’s technical culture including setting standards for algorithmic quality, scalability, and AI-first development. You will work on both generative and discriminative use cases, focusing on content generation at scale, gamification, benchmarking and analytics, multi-modal behavior classification from mobile signals, and continuously modernizing Outsmart’s SDLC.

Who You Are

10 + years experience in hands-on AI/ML role
Deep and proven experience with agentic engineering
Experience shipping AI-first applications at scale
Experience using AI effectively to contribute cross-platform
Demonstrable sense of Product, QA, and DevX
Ability to work autonomously in a fast‑paced environment

What You’ll Own

Co-ownership of AI-first SDLC
MCP/ML tooling
Contribute to prompting standards across the engineering team
Define and enforce benchmarks for AI applications
Work with Product and Engineering leadership to define AI roadmap
Own end-to-end deployment and maintenance of AI systems

What Helps You Succeed

Craftsmanship and Extreme Ownership
Open-mindedness
Frequent, direct, honest, kind communication
Demonstrable adoption of AI in all aspects of work
Track record of shipping in an environment of high-performance
User obsession

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.

Staff Applied AI Engineer