Director of Infrastructure Engineering

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 1.5M 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 hiring a Director of Infrastructure Engineering to lead our Infrastructure and Platform team, whose mission is to accelerate innovation and deliver operation stability through a combination of robust infrastructure, principled platformization, and empowering DevX.

You'll own hard problems, from deep-diving into a full infrastructure stack, to up-leveling DevX, to establishing automations, to hardening security, to evolving systems to be AI-native, to developing platform components. You will succeed with both strong organizational and people leadership skills, as well as exceptional hands-on development skills.

You might be a great fit for this role if:

• You are a deep infrastructure expert familiar with all common modern infra technologies, and you thrive in diving into details
• You understand platformization, and have deep experience building platform components that are principled, efficient, usable, and maintainable
• You have experience as an engineering manager in a fast-paced startup or growth-stage company, and enjoy supporting teams through change and scale, including managing engineers across multiple sites
• You bring strong technical judgment and a track record of leading engineering teams that ship impactful systems quickly and iteratively
• You’re passionate about education, access, and user experience, and motivated by a mission-driven environment
• You enjoy balancing technical decision-making with coaching, and you’re committed to building inclusive, high-performing teams
• You excel at owning and driving engineering roadmaps; collaborating with cross-functional partners to prioritize initiatives, align with business objectives, and ensure timely, high-quality execution

Core Responsibilities:

• Lead, mentor and grow a multi-site team of 5-10 engineers while remaining hands-on with architecture, technical direction, as well as day-to-day development
• Establish both short-term deliverables and long-term strategies across Outschool’s entire Infrastructure stack, including identifying and investing into opportunities for infra upgrade, platformization, and AI enablement as appropriate
• Partner cross-functionally with Product, Design, Data, Marketing and Operations to deliver an exceptional systems and experiences
• Partner with senior leadership to align on strategy, metrics and priorities
• Champion technical excellence and a culture of high ownership, providing mentorship, feedback, and support for the professional growth of engineers on your team
• Drive adoption of AI-development principles and agentic engineering workflows across the team

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
• Strong background in infrastructure and platform engineering, including deep expertise with AWS, Postgres, Kubernetes, Redshift, Terraform, Cloudwatch, and more
• Familiar with AI-native development paradigms and understands how to take teams through AI transformations
• Demonstrated ability to oversee multiple parallel projects from planning to execution and on time delivery
• Ability to align team goals with business objectives and contribute to strategic planning
• Experience in recruiting, hiring, and onboarding software engineers
• Excellent communication and stakeholder management skills, both written and verbal

Other Considerations:

• Experience in EdTech or building products for learners, educators, or families
• Experience with infrastructure upgrades, migrations, and consolidations
• 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. In addition to base compensation, this role is eligible for equity and benefits. Additional details are provided during the interview process.

For Canadian-based candidates, compensation range for this role 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, New York City, and Seattle Metro

US Tier 2: All California excluding San Francisco Bay Area, 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 - $357,500

US Tier 2: $221,000 - $303,875

US Tier 3: $195,000 - $268,125

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, and retirement plans
• Health: Comprehensive medical, dental, vision, disability, and life insurance
• Wellness: Annual wellness stipend, access to coaching & therapy, and pet wellness plans
• PTO & Family Benefits: Generous PTO and family leave policies
• Hybrid & Remote-Friendly: Outschool has a distributed team across the U.S. and Canada and an 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 and internet 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.