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.

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 - $325,000

US Tier 2: $221,000 - $276,250

US Tier 3: $195,000 - $243,750

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.

Benefits & Culture:

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, retirement plans.
• Health & Wellness: Comprehensive medical, dental, vision, disability, and life insurance — plus fertility/family planning coverage and access to ModernHealth coaching & therapy.
• PTO & Family Benefits: Generous PTO and family leave policies.
• Hybrid & Remote-Friendly: Outschool has a distributed team across the U.S. and Canada and a new 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, internet, and weekly meals 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.

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. Please note benefits and perks may vary for employees based outside of the US and Canada.

Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada, unless specifically indicated otherwise.

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.