Support Escalations Specialist

About the company

Outschool’s purpose is to help children develop a genuine love of learning. In a world that changes quickly, the standard education model often falls short of the varied and shifting needs of young learners. Outschool addresses this by offering flexible, engaging learning experiences that can complement or replace traditional schooling. Through a global online community of teachers and learners, the platform makes education more personalized, lively, and human.

Since launching its live online class marketplace in 2017, Outschool has grown substantially. It first gained traction with secular homeschool families, then expanded into enrichment learning for a broader audience. Since 2019, the business has grown 16x. After the pandemic, the platform expanded further into academic learning, added AI capabilities, and started building a larger international community. The company has supported more than 1.5 million learners and generates over $100 million in annual bookings.

Outschool values ambitious, curious, and driven people who are willing to challenge themselves, take calculated risks, and grow quickly. The team is focused on making a meaningful difference in education and seeks individuals who want to help learners approach the future with curiosity, resilience, and a lasting love of learning.

About the role

This position sits within the Customer Experience team and focuses on handling escalated support cases from parents and teachers. These are the requests that do not have straightforward answers, so the work requires independent judgment and the ability to make decisions without a fixed playbook. You may also occasionally work on Trust & Safety escalations, including highly sensitive situations.

The company gives preference to candidates located in the San Francisco Bay Area, though applicants outside the area may also be considered depending on experience and overall fit.

What you'll do

• Manage complex support tickets from parents and teachers, mainly through email.
• Assess unclear situations and choose an appropriate resolution under time constraints.
• Support occasional Trust & Safety cases that may involve sensitive material, including reports tied to minors, self-harm, or abuse.
• Explain decisions and outcomes clearly, including when the resolution is not the one the customer expected.
• Pass along relevant insights and recurring themes from case work to the wider CX team.

What we're looking for

• Excellent written communication skills, especially for delicate or difficult conversations.
• Strong judgment when facts are incomplete or ambiguous.
• The ability to make a call, explain the reasoning, and move forward efficiently.
• Comfort handling occasional emotionally heavy content without losing focus.
• Ability to work well on your own in a remote, high-pace environment.

Preferred background

• Experience in K–12 education.
• Prior startup experience.
• Background handling escalated support cases.
• Exposure to Trust & Safety, content moderation, or other roles that require careful judgment.

Hours and compensation

This role is expected to require 35 to 40 hours per week. The anticipated pay rate is $25.00 per hour.

Benefits and contract details

This is a contract position, so standard employee benefits are not included. If the contractor later converts to a full-time employee, a full benefits package would then be available.

Benefits and culture

• Competitive pay, stock options, and retirement plans.
• Medical, dental, vision, disability, and life insurance coverage.
• Annual wellness stipend, coaching and therapy access, and pet wellness support.
• Generous paid time off and family leave.
• Remote-friendly structure with a distributed team across the U.S. and Canada, plus a San Francisco office.
• Bay Area employees work in the office part of the week and receive commute-related support.
• Employees outside the Bay Area remain fully remote and can receive support for home office setup and internet expenses.
• Annual learning budgets for professional development and DEI education, plus funding for children to take Outschool classes.
• Matching gifts for eligible charities and support for Outschool.org nonprofit programs.

Equal opportunity and hiring notice

Outschool is an equal opportunity employer and considers diversity a moral responsibility and a business strength. Hiring decisions are based on relevant skills and experience, and the company does not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

If you need a reasonable accommodation during the application or interview process, you can contact recruiting@outschool.com.

Benefits are available only to full-time employees, and offerings may differ for employees outside the U.S. and Canada. Full-time employees must be citizens or legal residents of the U.S. or Canada and live in the U.S. or Canada, unless stated otherwise.

Application and data notice

When you apply, Outschool will use your personal information to assess your candidacy. Unless otherwise stated, the company hires employees only in the U.S. and Canada. Applicants elsewhere should note that their application may be discarded on submission, or the company may ask later whether it can be retained if a future match is being considered. If you are invited to interview, your data may be shared with interviewers and others involved in the process. If you are not hired, your application may be kept for one year in case another suitable role opens up. You can opt out at any time. Additional details are available in the Employee/Applicant Privacy Notice. As the process continues, the company will clarify what information is requested and how it will be used.