Principal Software Engineer

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

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.

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 [email protected].

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.