Director of Engineering, Outschool
$195-325k
+ Stock options. Salary dependent on location. For candidates in Canada: $220,000 - $275,000 CAD annually
Online interactive classes for children
Be an early applicant
Online interactive classes for children
1001+ employees
Be an early applicant
$195-325k
+ Stock options. Salary dependent on location. For candidates in Canada: $220,000 - $275,000 CAD annually
1001+ employees
Company mission
To inspire kids to love learning by linking learning to kids’ interests, connecting them with others who share those interests, and giving them the autonomy to pick their own path.
Role
Who you are
- 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
Desirable
- 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
What the job involves
- 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
- 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
Our take
Schooling has undergone some massive changes in recent years, with the needs of institutions and individuals changing quite radically. One company rising to meet these needs is Outschool, that operates an online platform for extracurricular classes.
Aimed at homeschooled students, Outschool saw a boom in business due to the pandemic in 2020, going on to achieve Unicorn status in 2021. Interestingly, though, it had already enjoyed swift growth and a place in Y Combinator years before lockdown began, and it has maintained an encouraging level of growth in the years since.
The hope of Outschool, and the tele-teaching sector at large, is that hybrid online/offline learning is here to stay - and interest in alternative education is certainly growing. With lucrative investment at its back, the company remains committed to empowering parents and students with a variety of flexible and personalized learning opportunities.
Steph
Company Specialist at Welcome to the Jungle
Insights
-5% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Oct 2021
$110m
SERIES D
Apr 2021
$75m
SERIES C
Total funding: $240.3m
Company benefits
- Share Financial Success: Stock options and a 401k that makes saving for retirement easier
- Health and 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 offer an additional wellness stipend and more resources related to mental and physical wellness
- PTO and Family Leave: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 virtual events as well as stipends for meals, remote work, and internet allowance. We offer an additional stipend for home office setup
- Lifelong Learners: Annual budget 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 501c3s, and has committed to supporting Outschool.org’s non-profit programs
Leadership
Andy Chiu
(CTO)Former VP of Engineering at Instacart. Spent 15 years at Google, ultimately as Senior Director of Software Engineering.
Xueyan Wang
(COO)Executive Member at enrich. Spent 9 years at Coursera, ultimately as SVP of Services and Business Operations. Also worked at Google for 9 years.
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