Full-Time
Director of Infrastructure Engineering
Outschool
1,001-5,000 employees
Online marketplace for live K-12 classes
Compensation Overview
CA$220k - CA$275k/yr
No H1B Sponsorship
Remote in USA + 1 more
More locations: Remote in Canada
Remote
Fully remote outside the San Francisco Bay Area; Bay Area-based employees work in the office part of the week.
US Citizenship, Canada Citizenship Required
 DevOps & Infrastructure (1) |
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- You have deep infrastructure expertise and familiarity with common modern infrastructure technologies.
- You understand platformization and have experience building principled, efficient, usable, and maintainable platform components.
- You have experience as an engineering manager in a fast-paced startup or growth-stage company, including managing engineers across multiple sites.
- You have a strong technical judgment and a track record of leading engineering teams that ship impactful systems quickly and iteratively.
- You have strong organizational and people leadership skills and exceptional hands-on development skills.
- You are experienced in owning and driving engineering roadmaps, collaborating with cross-functional partners, prioritizing initiatives, aligning with business objectives, and ensuring timely, high-quality execution.
- You have 10+ years of software engineering experience.
- You have 5+ years of engineering management experience leading medium-sized teams, including performance management, career development, and people logistics.
- You have a strong background in infrastructure and platform engineering, including expertise with AWS, Postgres, Kubernetes, Redshift, Terraform, and CloudWatch.
- You are familiar with AI-native development paradigms and taking teams through AI transformations.
- You can oversee multiple parallel projects from planning through execution and on-time delivery.
- You can align team goals with business objectives and contribute to strategic planning.
- You have experience recruiting, hiring, and onboarding software engineers.
- You have strong written and verbal communication and stakeholder management skills.
- Lead, mentor, and grow a multi-site team of 5-10 engineers while remaining hands-on with architecture, technical direction, and day-to-day development.
- Establish short-term deliverables and long-term strategies across the entire infrastructure stack, including infrastructure upgrades, platformization, and AI enablement.
- Partner cross-functionally with Product, Design, Data, Marketing, and Operations to deliver systems and experiences.
- Partner with senior leadership to align on strategy, metrics, and priorities.
- Champion technical excellence and a culture of high ownership while providing mentorship, feedback, and support for engineers’ professional growth.
- Drive adoption of AI-development principles and agentic engineering workflows across the team.
- 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.
Outschool is an online learning marketplace that connects families with live, interactive classes for children ages 3 to 18. It offers a wide range of subjects—from core academic topics to arts and crafts—through live sessions taught by experienced educators. Parents browse and enroll their children in classes, which are billed per class and generate commission income for the platform. Classes can be on-demand or scheduled as afterschool activities, providing flexible options to supplement traditional schooling or homeschooling. Outschool differentiates itself with a diverse catalog of classes and a marketplace model that scales by recruiting a broad network of teachers and offering a variety of subjects and formats. The company aims to expand access to flexible, high-quality education and support both students and teachers by growing its catalog and improving the platform for learning in K-12 contexts.
Company Size
1,001-5,000
Company Stage
Series D
Total Funding
$240.3M
Headquarters
San Francisco, California
Founded
2015
Get referred to Outschool
See people who can refer or advise you
Simplify's Take
What believers are saying
- June 3, 2025 OpenEd Academy partnership adds thousands of families and $100 credits.
- January 14, 2026 Mars event expanded nationally, strengthening brand and free acquisition.
- May 2026 showcase programs and August engineering hiring keep engagement and product momentum visible.
What critics are saying
- Outschool cut 18% in July 2022 and 25% in December 2022, showing demand volatility.
- Leadership transition on February 6, 2026 signals instability while competitors like Sora and OpenEd move faster.
- If paid-class demand weakens again, Outschool's marketplace model loses liquidity and educator supply.
What makes Outschool unique
- Outschool still offers 140,000 classes, spanning tutoring, hobbies, and microschool partnerships.
- Andy Chiu joined engineering in August 2026, signaling investment in personalization and platform quality.
- The OpenEd Academy and KaiPod deals embed Outschool inside alternative-school ecosystems.
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Benefits
Shared Financial Success - Competitive salaries, stock options and a 401(k) 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 provide employees with online access to coaching and therapy sessions through our partner, Modern Health.
PTO and Family Benefits - 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 expensable weekly meals, virtual events, expensable home office setup, and internet allowance.
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 donating $3M to Outschool.org non profit programs.
Growth & Insights and Company News
6 month growth
↑ 0%1 year growth
↑ 0%2 year growth
↑ 0%2026 Eddy Awards: Innovator of the Year - Daniel J. Lowe. Daniel J. Lowe is the 2026 Innovator of the Year. The Eddy Awards, presented by OpenEd and Outschool, recognize the people and resources advancing open and alternative education. The Innovator of the Year award honors someone who has created something new that meaningfully improves the homeschool experience for families beyond their own. Seven seperate families nominated this man. They all said some version of the same thing: he built a tool that changed how OpenEd, Inc. do school. One family put it simply: "We were ready to give up on homeschooling until Daniel created this." The tool. Daniel built Course Tracker, a free tool that homeschool families use to organize and track their children's education. It helps parents manage courses, assignments, grades, and progress across the sprawl of curricula, co-ops, and self-directed learning that makes up a homeschool life. He built it because his family needed it. Then he gave it away. No premium tier. No paywall. No monetization. Just a tool the community needed, built by someone who understood the problem because he lived it. That's why seven families wrote his name on a nomination form - not because of a marketing campaign or a viral post, but because the tool quietly solved a real problem. The story behind it. Daniel and his wife homeschool six kids across multiple curricula. The question that kept coming up: how much work does each child need to finish each week to actually finish the school year on time? His brother's advice - the same advice most homeschool families get - was to just do what you can and let unfinished work carry over. That approach put his wife on the edge of quitting. She didn't know when enough was enough for the day. She worried the kids were falling behind. The uncertainty was wearing them out. So Daniel built a spreadsheet. It tracked each child's curriculum and auto-adjusted week by week - if a child got ahead, the workload spread out; if they fell behind, it redistributed. Then he and his brother turned it into a simple website so it could be used from a phone during a real school day. Kids could log in, pick their subject, track their points, and submit work for approval. The rule was simple: hit your daily goal before 3 p.m. and video games are fair game. The stress disappeared when the work was gamified. That was 2018. They've finished their curriculum in the last week of the school year every year since. In Daniel's words. "I am thrilled that the Homeschool CourseTracker is being recognized for its role in enhancing the 'self-paced,' 'parent-defined' homeschooling learning experience. This recognition strengthens my commitment to helping parents be confident and successful in managing their children's homeschool experience." Charlie Deist Charlie Deist (aka "the OpenEd newsletter guy") is the editor of OpenEd Daily and Head of Content at OpenEd, where he curates compelling thoughts, trends, and tools for parents rethinking education. When he's not writing or wrangling content calendars, he's tending to a small homestead in rural Northern California, where he lives with his wife, four kids, and a rotating cast of cows, pigs, and chickens. Most of his best ideas come while hauling feed buckets or chasing animals that found a new way to escape. Join 20,000+ families receiving curated content to support personalized learning, every school day.
Outschool x MDRS: bringing space science to life for learners. Outschool has partnered with the Mars Desert Research Station (MDRS) to deliver an unforgettable Mars live event for families - connecting kids with the kind of hands-on exploration and real scientific thinking that fuels future innovators. Learn more: https://outschool.com/articles/mars-live-event
Outschool is excited to announce that Andy Chiu will be joining as Head of Engineering in August.
Enrolled Students to Receive $100 in Free Outschool Credits for 2025–26 School YearSAN FRANCISCO, June 3, 2025 /PRNewswire/ -- Outschool, the leading K–12 online learning platform, has partnered with OpenEd Academy, a newly launched accredited private school, to provide incoming students with up to $100 in free Outschool credits. This partnership brings thousands of live, interest-based classes and tutoring opportunities to OpenEd Academy families, broadening access to flexible, personalized learning experiences
Outschool Calls for More Personalized Learning Choices as Survey Shows Overwhelming Desire for Educational Reform, as well as Parental Fears about the Use of AI in EducationSAN FRANCISCO, March 26, 2025 /PRNewswire/ -- A new survey from leading online education platform Outschool, conducted by ResearchScape International in March 2025, reveals that while parents across the U.S. are divided about eliminating the Department of Education, they are overwhelmingly united in their belief that the traditional education system is failing to meet their children's needs. The survey polled 1,065 U.S. parents of children aged 5-18, highlighting an apparent demand for more personalized learning and greater parental control over their children's education