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Educator Experience Lead

Remote (U.S. & Canada)

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: 

Outschool is home to a global community of independent educators who create transformative learning experiences for kids and teens. We’re seeking an Educator Experience Lead to champion this community - helping educators feel confident, supported, and aligned as they grow on the platform.

In this role, you’ll lead the full educator journey—from onboarding and communications to programming, sentiment tracking, and internal advocacy. You’ll develop scalable processes and strategies that help educators thrive, and surface their voices to shape product, content, and platform evolution. Your work will be essential in strengthening trust, surfacing educator insights, and empowering educators to meet the evolving needs of Outschool learners around the world.

Core Responsibilities: 

  • Educator Communications & Feedback: Lead all educator-facing communications, including newsletters, platform updates, and help content. Track educator sentiment through tools like NPS and CSAT, and turn insights into action. Set the tone, timing, and messaging strategy to keep educators informed and engaged.
  • Educator Advocacy & Product Collaboration: Bring the educator perspective into conversations with Product, Design, and Marketing. Stay close to the educator experience—understanding class creation, tools, and challenges—and help shape improvements that make teaching on Outschool easier and more rewarding.
  • Onboarding & Early Success: Create clear, helpful onboarding experiences that guide new educators to their first successful class. Work closely with Product to embed onboarding best practices directly into the platform.
  • Community & Professional Learning: Design and manage programs that build community and support educator growth—from onboarding through long-term engagement. Empower experienced educators to lead and mentor others. Run scalable events, forums, and initiatives that foster connection and retention.

Experience & Skills

  • 5+ years in customer success, community management, education programming, or related roles (experience working with educators is a plus)
  • Strong communication skills—written, verbal, and strategic—with a deep empathy for educator needs.
  • Experience collaborating with Product and Design teams to improve user-facing tools, workflows, or in-product experiences.
  • Skilled in leveraging qualitative and quantitative data to drive program strategy.
  • Comfortable navigating cross-functional environments and advocating effectively for user perspectives.
  • Bonus: Background in teaching/education as well as experience working with authoring tools, CRM platforms, or in-product support design.

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 annual salary range for this role is $140,000 -$200,000. For Washington candidates outside of Seattle, as well as Colorado candidates, the salary range for this role is $125,000 -$180,000.


We use Covey as part of our hiring and / or promotional process for jobs in NYC and certain features may qualify it as an AEDT. As part of the evaluation process we provide Covey with job requirements and candidate submitted applications. We began using Covey Scout for Inbound on March 21, 2024.

Please see the independent bias audit report covering our use of Covey here.

Outschool Cares:

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.
  • 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: We create a remote culture through expensable 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 Outschool.org’s non-profit 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 recruiting@outschool.com.
 
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.

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