Job Application for Learning Experience Lead at Outschool

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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.

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 Elpha. Outschool 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.

About The Role:

We’re on a mission to improve the quality of learning experiences across our marketplace. We’re seeking a Learning Experience Lead to define what “great” looks like in an Outschool class—and to build the systems, tools, and standards that scale that greatness across our platform.

This role sits at the intersection of instructional design, learning science, and business analysis, and is ideal for someone who thinks like a learning architect and executes like a systems strategist. You’ll lead the effort to define and enforce quality standards, reduce variance in class effectiveness, and drive improvements in learner retention, conversion, and educator performance.

You’ll work closely with cross-functional partners across Product and Data to implement high-leverage interventions that improve retention and teacher practices at scale.

Core Responsibilities:

Define Clear Quality Standards: Codify “what great looks like” in an Outschool class based on learner behavior, retention, and engagement patterns. Build frameworks and rubrics to guide the design of effective, engaging, and learner-centric experiences.
Create Scalable Evaluation & Feedback Systems: Develop systems to assess educator quality and instructional design at scale—establish educator segmentation, feedback loops, and interventions. Identify the attributes of top-performing classes and translate them into actionable recommendations and templates.
Partner on Product & Tooling for Educators: Collaborate with Product to improve the class creation flow, embedding pedagogical nudges and quality signals directly into the educator experience. Recommend UX improvements and insights delivery mechanisms that help educators continuously improve their craft.
Drive Ongoing Insights: Surface trends around class effectiveness, learner engagement, and educator impact. Use these insights to evolve quality standards and inform new content formats, categories, or instructional approaches.

Desired Experience & Skills:

5+ years of experience in learning experience design, instructional strategy, or education product/operations.
Deep expertise in online learning design, including best practices for engagement, retention, and learner success.
Demonstrated ability to build scalable systems that guide instructional quality across large educator or creator networks.
Data-fluent: You use behavioral and retention data to drive design decisions and measure outcomes.
Strong cross-functional collaboration skills; you’ve worked closely with Product, Engineering, and Data teams to shape tools and systems.
Experience in a marketplace, creator platform, or EdTech environment is a strong plus.

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.

Learning Experience Lead

The Company:

Outschool Cares:

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