Principal AI Engineer

The Company

Outschool’s mission is to inspire kids to love learning. In our fast-changing world, the traditional educational system struggles to meet the diverse and evolving needs of young learners. Outschool reimagines this system, offering flexible and engaging learning experiences as a supplement and alternative to traditional education. By connecting learners with a global community of teachers and peers through our online platform, we make learning personal, dynamic, and deeply human.

We've made significant strides since launching our marketplace of live online classes in 2017. Finding initial success with secular homeschoolers, we then expanded to enrichment learning to meet the needs of a wider audience, growing our business 16x since 2019. Post-pandemic, we have evolved our platform to power academic learning, incorporated AI, and have begun to grow our international community. We're proud to have served over 1M passionate learners with more than $100M in annual bookings.   Driving disruptive, positive change in education is rewarding and hard. Outschool team members are encouraged to challenge themselves, take risks, and grow in their careers. We look for talented people whose sense of urgency, innate curiosity, and determination to drive impact will help Outschool achieve outsized results in pursuit of our mission. We invite you to be part of an ambitious team dedicated to ensuring every learner can navigate the future with curiosity, resilience, and a love of learning.

Outschool has been named Fast Company’s most innovative EdTech company in the world, and one of the top ten best startups for women from Elpha. Outschool has also been one of BuiltIn’s Best Remote Places to Work for the last two years and has appeared on Y Combinator’s Top Companies list for the last three years. 

The Role

We're seeking a Principal Engineer to lead the development of Outschool's AI-powered educational assistant - imagine interacting with an infinitely empowered school principal who can understand, guide, and enhance learning experiences. You'll create an intelligent agent that leverages our unique assets: thousands of hours of educational video, rich lesson transcripts, detailed learner preferences, and extensive marketplace interaction data. As we're pioneering new territory in AI-powered education, you'll need to think from first principles and be comfortable with 0->1 product development.

We are looking for candidates based in the SF/Bay Area or those who are open to frequent in person time in San Francisco. 

Key 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

What We're Looking For

Technical Leadership & Experience

• 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

Product & AI Focus

• 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

Cultural Alignment

• 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

Impact You'll Have

• Pioneer new applications of AI in educational technology
• Build systems that make expert educational guidance accessible to all
• Shape the future of human-AI interaction in learning environments
• Build and lead a team of engineers focused on AI innovation

#LI-Remote

We use Covey as part of our hiring and / or promotional process for jobs in NYC and certain features may qualify it as an AEDT. As part of the evaluation process we provide Covey with job requirements and candidate submitted applications. We began using Covey Scout for Inbound on March 21, 2024.

Please see the independent bias audit report covering our use of Covey here.

OUTSCHOOL CARES:

At Outschool, we believe that taking care of one another enables us to do our best work. To us that means:   •Shared Financial Success: Competitive salaries, stock options, and investment plans that make saving for retirement easier. •Health & Wellness: 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 & Family Benefits: PTO and family leave enable our team to take the time that we need to recharge, relax, and spend time with family and friends.  •Fully Distributed: 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. •Lifelong Learners: 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!  •Community Impact: Outschool matches employee donations to established charities and has committed to support Outschool.org’s non-profit programs.     Outschool is an equal opportunity employer. We view diversity as a moral imperative and competitive advantage. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We plan and structure our interviews to directly assess skills and experience.    If you require a reasonable accommodation to participate in the job application or interview process, please contact recruiting@outschool.com.   Benefits packages are included for full-time employees only. Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada.   Once you submit your application, Outschool will process your personal data to evaluate your candidacy for employment. Unless specifically indicated otherwise, we hire employees only in the U.S. and Canada. Applicants else where should be aware that we may discard your application upon submission or we may ask if you would like us to retain it later should there be consideration (this is not typical at all).  If you are selected for interviewing, your data will be shared with interviewers and personnel involved in that process. If not hired, your application will be retained for one year in case there is another suitable role. You may opt out of this at any time. Please see our Employee/Applicant Privacy Notice for more detailed information. If applicable, as you progress through the process, we will be clear about what information is being asked for and what happens with that information.