Support Escalations Specialist (6-Month Contract)

Outschool

20h•Remote

About The Position

As a Support Escalations Specialist on the CX team, you will be responsible for handling escalated tickets from parents and teachers. These tickets often lack obvious answers, requiring independent judgment calls without a predefined playbook. You will also occasionally manage Trust & Safety escalations, which may involve sensitive content. The role demands strong investigative, decision-making, and writing skills, and a capacity to resolve complex, ambiguous issues in a fast-paced environment. Outschool's mission is to inspire kids to love learning by offering flexible and engaging online learning experiences as a supplement and alternative to traditional education, connecting learners with a global community of teachers and peers.

Requirements

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

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

Benefits

Competitive salaries
stock options
retirement plans
Comprehensive medical, dental, vision, disability, and life insurance
fertility/family planning coverage
access to ModernHealth coaching & therapy
Generous PTO
family leave policies
commute-related benefits (for Bay Area–based employees)
support for expensable home office setup, internet, and weekly meals (for remote team members)
Annual budgets for professional development and DEI learning
budgets for children to take Outschool classes
Outschool matches employee donations to eligible charities
supports Outschool.org’s nonprofit programs