Customer Support Representative-Escalations

Outschool • Canada, KY

2h • $20 - $25 • Hybrid

About The Position

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.

Requirements

• 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 Haves

• 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

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

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Number of Employees: 101-250 employees