Escalations Specialist

Customer Experience Representative

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.

• 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

• 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

• 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

• 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.

• 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.

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, retirement plans.
• Health & Wellness:
  Comprehensive medical, dental, vision, disability, and life insurance — plus fertility/family planning coverage and access to Modern Health coaching & therapy.
• PTO & Family Benefits:
  Generous PTO and family leave policies.
• Hybrid & Remote-Friendly:
  Outschool has a distributed team across the U.S. and Canada and a new office in San Francisco. Bay Area–based employees work in the office part of the week and receive commute-related benefits. Team members outside the Bay Area remain fully remote, with support for expensable home office setup, internet, and weekly meals to stay connected no matter where you are.
• Lifelong Learners:
  Annual budgets for professional development and DEI learning; budgets for children to take Outschool classes.
• Community Impact:
  Outschool matches employee donations to eligible charities and supports Outschool.org's nonprofit programs.

Outschool is an equal opportunity employer. We view diversity as a moral imperative and competitive advantage. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We plan and structure our interviews to directly assess skills and experience.