Director of Engineering
outschool • Remote (U.S. & Canada)
Posted: May 27, 2026
Job Description
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.
Additional Content
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.