Principal Software Engineer
outschool • Remote (U.S. & Canada)
Posted: May 19, 2026
Job Description
The Role
Outschool is looking for a Principal Software Engineer to help build key products using an agentic-first development approach. You'll contribute to building innovative 0-to-1 products, and act as a critical lead to push forward Outschool’s AI development transformation. While this is primarily a deep individual contributor role, you will also have the opportunity to step into light leadership and people management responsibilities as needed.
This is an ideal opportunity for someone who is deeply enthusiastic about building with AI, and deeply passionate about shipping real education impact for millions of families. This is also an exciting opportunity for someone who can go deep into product building in a new space, and who can also go wide to be a force-multiplier for the entire engineering organization to advance our AI posture.
Core Responsibilities:
- Act as a critical contributor to developing key products from Outschool, participating and demonstrating exemplary proficiency in domain understanding, user empathy, engineering design, system quality, and cross-functional collaboration
- Execute true 0-to-1 efforts with an innovative and action-oriented mindset, embracing ambiguity as an opportunity rather than a challenge
- Lead Outschool’s AI-native development transformation both as a cross-team lead and as a deep IC who leads by example
- Take on people management responsibilities as needed, like day-to-day support, performance management, and career development
- Act as a senior engineering leader to shape Outschool’s engineering culture and processes, particularly with an AI angle
- Contribute to hiring by helping identify, interview, and onboard strong engineering talent
- Participate in stand-ups, sprint planning, retros, production deployments, and on-call rotations
Desired Experience & Skills:
- 10+ years of software engineering experience
- Proficiency in full-stack development: TypeScript, React, Node.js, GraphQL, and PostgreSQL
- Proven track record of demonstrating proficiency in AI-native development, and leading teams into it
- Senior technical leadership: you've set direction, made architectural calls, and raised the bar for a team
- Experience with or strong interest in people management: you're a natural mentor who invests in the growth of those around you
- Strong communication and collaboration skills: you can translate technical complexity into clarity for engineers, product partners, and leadership alike
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 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: $216,750 - $270,000
US Tier 2: $184,238 - $229,500
US Tier 3: $162,000-202,500
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
Outschool is looking for a Principal Software Engineer to help build key products using an agentic-first development approach. You'll contribute to building innovative 0-to-1 products, and act as a critical lead to push forward Outschool’s AI development transformation. While this is primarily a deep individual contributor role, you will also have the opportunity to step into light leadership and people management responsibilities as needed.
This is an ideal opportunity for someone who is deeply enthusiastic about building with AI, and deeply passionate about shipping real education impact for millions of families. This is also an exciting opportunity for someone who can go deep into product building in a new space, and who can also go wide to be a force-multiplier for the entire engineering organization to advance our AI posture.
Core Responsibilities:
- Act as a critical contributor to developing key products from Outschool, participating and demonstrating exemplary proficiency in domain understanding, user empathy, engineering design, system quality, and cross-functional collaboration
- Execute true 0-to-1 efforts with an innovative and action-oriented mindset, embracing ambiguity as an opportunity rather than a challenge
- Lead Outschool’s AI-native development transformation both as a cross-team lead and as a deep IC who leads by example
- Take on people management responsibilities as needed, like day-to-day support, performance management, and career development
- Act as a senior engineering leader to shape Outschool’s engineering culture and processes, particularly with an AI angle
- Contribute to hiring by helping identify, interview, and onboard strong engineering talent
- Participate in stand-ups, sprint planning, retros, production deployments, and on-call rotations
Desired Experience & Skills:
- 10+ years of software engineering experience
- Proficiency in full-stack development: TypeScript, React, Node.js, GraphQL, and PostgreSQL
- Proven track record of demonstrating proficiency in AI-native development, and leading teams into it
- Senior technical leadership: you've set direction, made architectural calls, and raised the bar for a team
- Experience with or strong interest in people management: you're a natural mentor who invests in the growth of those around you
- Strong communication and collaboration skills: you can translate technical complexity into clarity for engineers, product partners, and leadership alike
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 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: $216,750 - $270,000
US Tier 2: $184,238 - $229,500
US Tier 3: $162,000-202,500
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.