Support Escalations Specialist (6-Month Contract)

Remote (U.S.); San FranciscoRemotePosted 5 weeks ago

Role Overview

Outschool is hiring a Support Escalations Specialist (6-Month Contract). This is a contract remote role, with the team based in (U.S.); San Francisco. Full responsibilities, required qualifications, and the apply link are listed in the description below.

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Job description

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.

About The Role:

As part of the CX team, you'll handle escalated tickets from parents and teachers - the ones without an obvious answer, where you'll be making independent judgment calls without a playbook for every situation. You'll also occasionally handle Trust & Safety escalations, which can include sensitive content. We're looking for someone with strong investigative, decision-making, and writing skills who thrives on resolving complex, ambiguous issues in a fast-paced environment.

We prioritize candidates based in the San Francisco Bay Area. That said, we are open to candidates outside the Bay Area based on experience and fit.

Core 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 Experience & Skills:

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

Nice to Haves:

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

Hours and Compensation:

Outschool recruits across the U.S. and Canada. This role is anticipated to work 35-40 hours per week, with an anticipated hourly rate of $25.00.

Benefits:

This is a contract role. As a contractor, benefits are not included; however, a full benefits package would be available if converted to a full-time employee.

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 recruiting@outschool.com.

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.

About Outschool

Outschool

outschool.org

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Frequently Asked Questions

How do I apply for the Support Escalations Specialist (6-Month Contract) position at Outschool?

Use the Apply button above to submit your application directly to Outschool. Most applications take less than 5 minutes if your resume and contact details are ready, and you'll be routed to the employer's official application system to finish.

Is the Support Escalations Specialist (6-Month Contract) role at Outschool remote?

Yes. This is a remote role. The team is based in (U.S.); San Francisco, but the position itself does not require relocating to that office.

What does a Support Escalations Specialist (6-Month Contract) at Outschool earn?

Outschool has not disclosed a salary range in this posting. Many employers share specifics later in the interview process; you can also ask during a recruiter screen if compensation transparency is important to you.

When was the Support Escalations Specialist (6-Month Contract) role at Outschool posted?

This role was posted on June 13, 2026 (40 days ago). It's still listed as actively hiring; we re-confirm openings against the source system multiple times per day and remove closed roles.

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