Support Escalations Specialist (6-Month Contract)

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-Fr