Staff Applied AI Engineer

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.

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.

• 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

• 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

• 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