Support Escalations Specialist (6-Month Contract)

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.