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.