Customer Support Representative - Escalations [Contract]
Outschool
Posted: January 21, 2026
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Quick Summary
Customer Support Representative - Escalations [Contract] is a remote position that requires a customer support representative to handle customer inquiries and resolve issues via phone, email, and chat. The ideal candidate should have excellent communication and problem-solving skills, as well as the ability to work independently and manage multiple tasks simultaneously. The role involves providing top-notch customer service and ensuring a high level of customer satisfaction.
Required Skills
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 1M 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 Customer Support team, you will help ensure every parent, teacher, and learner in the Outschool community has a great experience. We’re hiring multiple Customer Support Representatives who will become experts in Outschool’s inner workings, primarily handling customer support conversations via chat and email. We’re looking for people with strong investigative, decision-making, and writing skills who can work independently to resolve complex, sometimes ambiguous issues in a fast-paced environment.
Core Responsibilities:
• Provide high-quality product support to parents and teachers, primarily via chat and email
• Resolve customer inquiries with empathy, clarity, and sound judgment
• Handle more complex or sensitive support situations, escalating internally when appropriate
• Follow established workflows while adapting to new products, tools, and policies
• Take on additional CX-related tasks as needed to support team operations
Desired Experience & Skills:
• Quick learner with a passion for Outschool
• Strong written communication skills with a customer-first mindset
• Comfortable working independently and making decisions within defined guidelines
• Thrives in a fast-changing environment, with a track record of adapting to new products and features
Nice to Have:
• Experience in K–12 education
• Startup experience
• Bachelor degree
• Background in escalated support or QA of customer interactions
• Technical aptitude or experience supporting software products with complex workflows
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 $20 - 25.
• Hours are flexible within daytime US based hours and will include 1 weekend day.
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, retirement plans.
• Health & Wellness: Comprehensive medical, dental, vision, disability, and life insurance — plus fertility/family planning coverage and access to ModernHealth 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.
If you require a reasonable accommodation to participate in the job application or interview process, please contact [email protected].
Benefits packages are included for full-time employees only. Please note benefits and perks may vary for employees based outside of the US and Canada.
Full-time employees must be a citizen or legal residents 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 else where 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 (this is not typical at all). 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.