Contract

Support Escalations Specialist

Outschool

Outschool

1,001-5,000 employees

Online marketplace for live K-12 classes

Compensation Overview

$25/hr

Remote in USA + 1 more

More locations: San Francisco, CA, USA

Hybrid

Bay Area employees work in the office part of the week; others may remain fully remote.

Category
Customer Experience & Support (1)

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Responsibilities
  • Resolve escalated customer support tickets from parents and teachers, primarily via email
  • Investigate ambiguous situations and make sound decisions under time pressure
  • Handle occasional Trust & Safety escalations, which may involve sensitive content including reports related to minors, self-harm, or abuse
  • Communicate outcomes clearly and with care, including when the answer isn't what the customer hoped for
  • Share useful context and feedback from your ticket work with the broader CX team
Desired Qualifications
  • Strong written communication, especially for difficult or sensitive conversations
  • Judgment under ambiguity: you can make a decision, explain your reasoning, and keep moving
  • Able to engage with occasional heavy content without it derailing your work
  • Comfortable working independently in a remote, fast-paced environment
  • Experience in K–12 education
  • Startup experience
  • Prior experience with escalated support tickets
  • Prior exposure to Trust & Safety, content moderation, or other judgment-heavy work

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

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Simplify Jobs

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

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
Opened
Mar 26th, 2026
2026 Eddy Awards: Innovator of the Year - Daniel J. Lowe.

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
Jan 23rd, 2026
Outschool x MDRS: Bringing Space Science to Life for Learners

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
Aug 26th, 2025
Outschool Welcomes Andy Chiu as Head of Engineering

Outschool is excited to announce that Andy Chiu will be joining as Head of Engineering in August.

PR Newswire
Jun 3rd, 2025
Outschool Partners With Opened Academy To Expand Access To Personalized Learning

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

PR Newswire
Mar 26th, 2025
New Survey Finds Parents Divided On Eliminating Department Of Education But United In Desire For Change And Interest In Education Savings Accounts (Esas)

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