Support Escalations Specialist (6-Month Contract)

Role Summary

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.

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

Requirements

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.