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 1.5M passionate learners with more than $100M in annual bookings.The Role
We’re hiring a Director of Engineering to lead a strong product engineering team developing Outschool’s mission-critical products, including and in particular a new AI-powered platform that transforms how families are able to navigate the complex world of alternative education while getting reimbursed through public-funding programs. This role will be responsible both for developing 0-to-1 products from the ground up, as well as scaling user journeys on Outschool’s existing marketplace. This is a highly impactful leadership role that combines technical strategy, people leadership, and hands-on development. The ideal candidate will shape not only Outschool’s most critical products, but also our engineering culture, talent growth, as well as AI-native development models, all while delivering meaningful educational impact to millions of families.
Core Responsibilities:
- Lead, mentor, and grow a team of 5–10 engineers while remaining hands-on with architecture, system design, and technical direction
- Contribute directly to the codebase as an individual contributor, helping accelerate development velocity and establish high engineering standards
- Lead engineering strategy and execution for a brand-new, high-priority initiative
- Partner cross-functionally with Product, Design, Data, Marketing and Operations to deliver an exceptional parent experience
- Collaborate with senior leadership to align on strategy, priorities, metrics, and long-term roadmap planning
- Foster a culture of technical excellence, ownership, experimentation, and continuous growth through mentorship and feedback
- Lead adoption of AI-development principles and agentic engineering workflows across the organization
- Help define and implement modern engineering practices that leverage AI to improve developer speed and productivity, and product quality
Desired Experience & Skills:
- 10+ years of software engineering experience
- 5+ years of engineering management experience leading medium-sized teams, with demonstrated proficiency in performance management, career development, and people logistics
- Familiar with AI-native development paradigms and understands how to take teams through AI transformations
- Strong experience with full-stack development: TypeScript, React, Node.js, GraphQL, and PostgreSQL
- Experience balancing engineering leadership responsibilities with hands-on coding and technical contribution
- Proven ability to lead multiple complex initiatives from planning through execution and delivery
- Data-driven mindset with experience leveraging experimentation, A/B testing, analytics, and metrics to inform decisions
- Ability to align engineering execution with broader business and product strategy
- Experience recruiting, hiring, and scaling high-performing engineering teams
- Excellent communication and stakeholder management skills across technical and non-technical audiences
Other Considerations:
- Experience in EdTech or building products for learners, educators, or families
- Familiarity with search and discovery systems
- Background in marketplace technologies
- Experience at a fast-paced startup or high-growth company
Compensation:
Outschool recruits across the US and Canada, and sets employee salaries to reflect local compensation and cost of living.
This role is available in Canada:
The salary range for this position is $220,000 - 275,000 CAD annually.
This role is available in the following US Pay Zones:
US Tiers
US Tier 1: San Francisco Bay Area and New York City
US Tier 2: All California excluding San Francisco Bay Area, Seattle Metro, Boston Metro, Chicago Metro, Denver Metro, Austin Metro, Portland Metro
US Tier 3: All other cities and states
US Pay Zones
US Tier 1: $260,000 - $357,500
US Tier 2: $221,000 - $303,875
US Tier 3: $195,000 - $268,125
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.
- Shared Financial Success: Competitive salaries, stock options, and retirement plans
- Health: Comprehensive medical, dental, vision, disability, and life insurance
- Wellness: Annual wellness stipend, access to coaching & therapy, and pet wellness plans
- PTO & Family Benefits: Generous PTO and family leave policies
- Hybrid & Remote-Friendly: Outschool has a distributed team across the U.S. and Canada and an office in San Francisco. Bay Area-based employees work in the office part of the week and receive commute-related benefits. Team members outside the Bay Area remain fully remote, with support for expensable home office setup and internet to stay connected no matter where you are.
- Lifelong Learners: Annual budgets for professional development and DEI learning; budgets for children to take Outschool classes
- Community Impact: Outschool matches employee donations to eligible charities and supports Outschool.org’s nonprofit 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.
Skills Required
- 10+ years of software engineering experience
- 5+ years of engineering management experience leading medium-sized teams
- Familiar with AI-native development paradigms
- Strong experience with full-stack development
- Proven ability to lead multiple complex initiatives
- Experience recruiting, hiring, and scaling high-performing teams
- Excellent communication and stakeholder management skills
What We Do
Outschool is an online learning platform that empowers kids 3-18 to learn on their own terms with the widest variety of teachers, topics, and classes to suit any interest. We offer interactive, small-group classes via video that are fun and social, can be taken any time, and clubs that connect learners around their favorite topics. With Outschool, learners are free to pursue their interests, connect with others around shared passions, and build confidence through progress. Since 2015, we’ve partnered with vetted, diverse, expert teachers to give kids everywhere greater access to high-quality education. With Outschool, kids can go beyond the classroom to discover topics they love.
Why Work With Us
We exist to set learning free, to break through the barriers to education, increase access and give back control. For every kid pursuing any interest. For every parent seeking greater choice. For every teacher not satisfied with the status quo. We’re here to unleash the love of learning by reimagining what education can be.
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