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.
About the Role
We're seeking an exceptional engineering leader to drive technical innovation and transformation, with a special focus on AI/ML-driven personalization and recommendations for our marketplace. The ideal candidate will either have experience transforming engineering cultures or building high-performance engineering organizations from the ground up. This role combines hands-on technical leadership with strategic vision to scale our platform and drive significant business impact. This role will report into the Head of Outschool/CEO.
At Outschool, we’ve decided to take an unconventional approach to titles that aligns with our values and is more focused on impact above status - this role would typically be called a VP or SVP of Engineering and we are looking for candidates who bring that level of experience to the role. You can read more about our titling philosophy here.
Key Responsibilities
- Lead technical strategy and hands-on development of AI/ML capabilities, focusing on personalization and recommendations
- Drive engineering excellence through mentorship, best practices, and quality standards
- Transform or build engineering culture focused on learning, innovation, and high performance
- Scale technical operations while maintaining agility and innovation
- Architect and implement core platform capabilities
- Establish data-driven performance metrics aligned with business objectives
- Foster deep collaboration between engineering, product, and design teams
- Build and retain world-class engineering talent
- Drive technical decisions that create competitive advantages
- Lead evaluation and modernization of technical stack
About You
You're a technical leader who combines deep engineering expertise with strong cultural leadership. You have a track record of either transforming engineering organizations or building high-performing teams from scratch. You're hands-on, strategic, and passionate about using technology to drive business impact.
Required Experience & Skills
- Deep expertise in AI/ML, particularly recommendation systems and personalization
- Strong coding abilities and system design experience
- 10+ years engineering leadership experience
- Led engineering organizations of 30+ people
- Track record of successful product launches in consumer marketplaces or consumer software is critical
- Experience scaling technical platforms
- Proven ability to attract, develop and retain exceptional talent
- Strong technical decision-making capabilities
- Excellence in stakeholder communication and management
- Preference for SF/Bay area or a willingness to travel regularly for in-person time with our team
How We Work
Our Values
Our organization is built on three core values that shape everything we do:
Learning By Doing
We value learning by doing, using startup methods, which inherently means embracing risk and change. We look to the future rather than holding onto the past. We are positive, bold and resilient to setbacks. We hone our craft by trying new approaches and learning together.
Scaling For Impact
We value scaling to grow our impact for many more learners. Achieving scale requires building a large, profitable, global business to enable our mission for the long-term. We use our scale to better understand, and sustainably serve, the broad and diverse needs of all learners.
Disrupting The Status Quo
We value disrupting the status quo in service of our mission. The status-quo education system is unacceptable to us, so we are willing to embrace challenge, discomfort and even controversy in service of fast progress. We make hard decisions, take ownership and bias towards action.
Our Leadership Principles
These core values manifest in how we work every day:
Learning By Doing
- Embrace experimentation and calculated risks
- Learn through rapid iteration and feedback
- Stay resilient through setbacks
- Focus on continuous improvement
Scaling For Impact
- Build for growth while maintaining quality
- Make data-driven decisions
- Think strategically about long-term scalability
- Balance speed with sustainability
Drive Change & Innovation
- Push boundaries in technical solutions
- Challenge status quo when needed
- Maintain strong opinions, loosely held
- Embrace and drive transformation
Hands-On Leadership
- Actively participate in technical discussions
- Deliver high-quality output
- Remove obstacles for the team
- Maintain attention to detail
Company First
- Prioritize long-term company success
- Make decisions aligned with strategic goals
- Focus on collective impact
- Build for the greater good
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!
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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
[email protected].
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.