Principal AI Engineer

Summary

Join Outschool as a Principal Engineer to spearhead the development of an AI-powered educational assistant. You will design and build this intelligent agent from the ground up, leveraging existing educational content and data. This role requires strong technical leadership and experience in building production AI applications, particularly with LLMs and conversational interfaces. You will lead technical implementation, establish responsible AI development patterns, and mentor engineers. The ideal candidate possesses strong product intuition, a user-centric approach, and aligns with Outschool's company culture. Based in the SF Bay Area or open to frequent in-person time in San Francisco is required.

Requirements

• Current Staff or Principal Engineer with proven track record building production AI applications
• Demonstrated ability to lead 0->1 product development in fast-paced environments
• Experience building consumer-facing AI features, particularly with LLMs and conversational interfaces
• Strong technical breadth across full stack development, data processing, and AI systems
• Track record of building reliable, scalable products from concept to production
• Track record of being scrappy and hands-on a growth stage company
• History of building and scaling engineering teams
• Strong product intuition and user-centric approach to development
• Demonstrated excitement for AI application development
• Ability to think from first principles in new domains
• Experience working directly with product leadership to shape technical direction
• Clear judgment in balancing rapid iteration with scalable foundations
• Learning By Doing : Embraces risk, tries new approaches, and learns from setbacks
• Biased To Action : Makes quick, decisive choices while maintaining high standards
• Hands On : Takes initiative, dives into details, and removes obstacles to maintain momentum
• Engaged : Works with intense focus and connects actively with teams and responsibilities
• Opinionated : Expresses strong perspectives while remaining open to new ideas/information
• Company First : Prioritizes overall success above individual preferences

Responsibilities

• Design and build our AI-powered educational assistant from the ground up, iterating rapidly on core features
• Create scalable systems that effectively utilize our rich educational content across video, text, and user interaction data
• Lead technical implementation of AI features while maintaining a strong user-centric focus
• Establish patterns for responsible AI development, testing, and monitoring
• Guide and mentor engineers in building AI-powered features
• Partner closely with product leadership to evolve our AI strategy and roadmap

Benefits

• Competitive salaries, stock options, and investment plans that make saving for retirement easier
• Comprehensive health, dental, vision, disability, and life insurance coverage options for employees and their families. Our medical benefits include fertility and family planning coverage. We also provide employees with online access to coaching and therapy sessions through our partner, ModernHealth
• PTO and family leave enable our team to take the time that we need to recharge, relax, and spend time with family and friends
• With a team distributed across the US and Canada, we create a remote culture through expensable meals, virtual events, expensable home office setup, and internet allowance
• Annual budgets to self-direct our professional development as well as DEI learning. There’s also a budget for employees’ learners to take classes on Outschool!
• Outschool matches employee donations to established charities and has committed to support Outschool.org’s non-profit programs