Support Escalations Specialist (6-Month Contract)

OutschoolSan Francisco, CA
Hybrid

About The Position

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.

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
  • Annual wellness stipend
  • Access to coaching & therapy
  • Pet wellness plans
  • Generous PTO and family leave policies
  • Support for expensable home office setup and internet
  • Annual budgets for professional development and DEI learning
  • Budgets for children to take Outschool classes
  • Outschool matches employee donations to eligible charities and supports Outschool.org’s nonprofit programs
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