Support Escalations Specialist (6-Month Contract)
About this role
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.
Company at a glance
Outschool is an online learning marketplace built around kids' actual interests, not a standardized curriculum or a system that decides what they should learn when.
We connect families with live and self-paced classes across thousands of subjects, taught by teachers who chose this path because they love what they teach. Whether your kid is exploring something brand new, doubling down on a passion, or learning in a way that works for their brain, we're here to make that possible.
We work with families pursuing every kind of alternative education: homeschoolers, ESA families, hybrid learners, and parents building something custom. We work with neurodivergent kids. We work with kids learning at their own pace. We work with families who've tried traditional school and want something different.
The best learning happens when kids are curious. When a teacher is genuinely excited about what they're teaching. When a parent trusts their instincts about their child's education. We're here to make that easier. Follow us to see what families are building, what teachers are creating, and what we're learning along the way.
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