Support Escalations Specialist (6-Month Contract)

Outschool; San Francisco (CA); Hybrid; USD 28,413 - 40,467; Part time

Benefits offered by this job

Competitive salaries

Stock options

Comprehensive health insurance

PTO and family leave policies

Annual wellness stipend

Job summary

Outschool is seeking a Customer Experience Specialist to join their team in San Francisco. In this role, you'll handle escalated tickets from parents and teachers, requiring excellent judgment and decision-making skills. Your ability to communicate effectively will be crucial, especially when dealing with sensitive topics. Candidates in the San Francisco Bay Area are prioritized, but all qualified applicants are welcome.

The position offers a flexible work environment with varying hours. A competitive hourly rate of $25 is anticipated, along with a range of potential perks and benefits.

Qualifications

• Strong written communication for sensitive conversations is essential.
• Ability to make decisions under ambiguous circumstances and explain reasoning clearly.
• Comfortable dealing with challenging content without derailing work.

Responsibilities

• Resolve escalated customer support tickets from parents and teachers via email.
• Investigate ambiguous situations and make sound decisions under time pressure.
• Handle Trust & Safety escalations involving sensitive content, including reports related to minors.

Skills

Strong written communication

Judgment under ambiguity

Ability to engage with heavy content

Comfortable working independently

Education

Experience in K–12 education

Job description

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.

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: ability to make a decision, explain your reasoning, and keep moving.
• Ability 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

• 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‑Friendly: Outschool has a distributed team across the U.S. and Canada and an 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 and internet 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.

If you require a reasonable accommodation to participate in the job application or interview process, please contact [e-mail].

Benefits packages are included for full‑time employees only. Please note benefits and perks may vary for employees based outside of the U.S. and Canada. Full‑time employees must be a citizen or legal resident of the U.S. or Canada and reside in U.S. or Canada, unless specifically indicated otherwise.

Once you submit your application, Outschool will process your personal data to evaluate your candidacy for employment. Unless specifically indicated otherwise, we hire employees only in the U.S. and Canada. Applicants elsewhere should be aware that we may discard your application upon submission or we may ask if you would like us to retain it later should there be consideration. If you are selected for interviewing, your data will be shared with interviewers and personnel involved in that process. If not hired, your application will be retained for one year in case there is another suitable role. You may opt out of this at any time. Please see our Employee/Applicant Privacy Notice for more detailed information. If applicable, as you progress through the process, we will be clear about what information is being asked for and what happens with that information.