Support Escalations Specialist (USA & Canada)

Outschool’s mission is to inspire kids to love learning. We achieve this by linking learning to kids’ interests, connecting them with other classmates who share their passions, and giving them the autonomy to pick their own paths. Our small group classes meet over live video chat with teachers who celebrate their unique strengths and empower all learners to develop confidence and a strong sense of self.

We’re also focused on removing barriers for historically underserved learners who face systemic challenges to their success. is a nonprofit that partners with homeschooling co-ops, community-based organizations, and schools across the U.S. to provide marginalized communities with access to virtual and hybrid learning experiences.

We believe that diversity drives learning. To meet our mission, we encourage, support, and celebrate different ideas, perspectives, and backgrounds. As a fully distributed (remote) team, we challenge one another to find the most effective way to empower learners, teachers, and parents. Your name, race, religion, gender, nationality, sexual orientation, and age are not barriers; they are why we want to work with you. We invite talented and creative candidates who value the importance of nurturing a child’s boundless curiosity to join us on this journey.

The pandemic has been challenging for families all over the globe. We acted quickly and worked together to provide quality resources to learners, parents, and teachers in the past year. As communities worldwide rethink their approach to education, Outschool will continue to innovate and provide kids with unique opportunities to explore their passions.

Outschool has been named Fast Company’s most innovative EdTech company in the world, and one of the top ten best startups for women from ElphaOutschool has also been one of BuiltIn’s Best Remote Places to Work for the last two years and has appeared on Y Combinator’s Top Companies list for the last three years. 

The Role

As part of the Support Escalations team, you will play a central role in enhancing the Outschool customer experience. Your primary focus will be to minimize ticket escalations and identify opportunities to increase efficiencies in our support workflows. By collaborating with our outsourced team of agents and harnessing the power of AI, you’ll aim to reduce the percentage of escalated tickets. Your critical thinking skills will be crucial in pinpointing opportunities for the Support team to become more efficient, ultimately providing top-tier service. Your contributions will be instrumental in shaping a seamless educational experience for our community while optimizing support operations. 


  • Provide email support to parents and educators with complex and escalated product issues 
  • Reduce the percentage of escalated tickets by developing strategies to tackle recurring challenging issues at their root, ensuring that similar cases can be efficiently handled by our outsourced team or AI in the future 
  • Play an active role in training our outsourced agents handling escalated cases 
  • Apply critical thinking to identify opportunities for enhancing the efficiency of workflows and processes for escalated tickets 
  • Advocate for reducing friction in the customer experience by proactively identifying and surfacing pain points 


  • Demonstrated experience as a top performer in customer support, specializing in reducing ticket escalations and driving operational efficiencies
  • Proven ability to handle complex and escalated customer issues with a track record of finding solutions that minimize escalations 
  • Ability to quickly learn and demonstrate a passion for Outschool
  • Excellent verbal and written communication skills
  • Thriving in a rapidly shifting dynamic environment, track record of keeping up with product changes and evolving support processes 

Outschool recruits across the US and Canada, and sets employee salaries to reflect local compensation and cost of living. For New York and California candidates, as well as candidates based in Seattle, WA the salary range for this role would be $75,000-$90,000 USD.

For Washington candidates outside of Seattle, as well as Colorado candidates, the salary range for this role would be $67,500-$81,000 USD.


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, and investment plans that make saving for retirement easier.

•Health & Wellness: Comprehensive health, dental, vision, disability, and life insurance coverage options for employees and their families. Our medical benefits include fertility and family planning coverage. We also provide employees with online access to coaching and therapy sessions through our partner, ModernHealth. 

•PTO & Family Benefits: PTO and family leave enable our team to take the time that we need to recharge, relax, and spend time with family and friends. 

•Fully Distributed: With a team distributed across the US and Canada, we create a remote culture through expensable weekly meals, virtual events, expensable home office setup, and internet allowance.

•Lifelong Learners: Annual budgets to self-direct our professional development as well as DEI learning. There’s also a budget for employees’ learners to take classes on Outschool! 

•Community Impact: Outschool matches employee donations to established charities and has committed to support’s non-profit programs.

Benefits packages are included for full-time employees only.

Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada.