Outschool

AI Enablement Specialist

Revenue & AR Accounting Manager

Engineering Manager

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Experienced Software Engineer

Outschool is seeking an AI Enablement Specialist to train, test, and fine-tune AI systems for customer support. This role involves improving AI accuracy, empathy, and resolution rates, translating product functionality into AI-ready documentation, and auditing AI-driven support flows. The ideal candidate is curious about AI, thrives in ambiguity, and is passionate about transforming customer experience through experimentation and continuous improvement of AI systems and documentation.

<h3 class="text-xl md:text-2xl font-bold mt-8 mb-3 text-gray-800">The Company:</h3><p class="my-4 text-gray-700 leading-relaxed">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.</p><p class="my-4 text-gray-700 leading-relaxed">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.</p><p class="my-4 text-gray-700 leading-relaxed">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.</p><h3 class="text-xl md:text-2xl font-bold mt-8 mb-3 text-gray-800">About The Role:</h3><p class="my-4 text-gray-700 leading-relaxed">We’re looking for someone who’s excited to be at the edge of how AI transforms customer support. We’re looking for curiosity, passion, and drive - we don’t expect candidates to come in with direct experience. If you’re curious about AI, thrive in ambiguity, and love the idea of shaping how humans and AI work together, this is an opportunity to make an immediate impact.</p><p class="my-4 text-gray-700 leading-relaxed">As our AI Enablement Specialist, you’ll train, test, and fine-tune AI systems that power our customer support. You’ll make sure product changes are captured clearly for AI, and you’ll push the boundaries of what AI can do by analyzing performance, spotting gaps, and experimenting with improvements.</p><p class="my-4 text-gray-700 leading-relaxed">The ideal candidate is energized by the possibilities of AI and passionate about experimenting to transform the customer experience. They have strong attention to detail, show initiative as a self-starter, and bring a voracious appetite for learning new skills quickly. They are comfortable with ambiguity and motivated to simplify complex problems into clear solutions for customers and AI.</p><h3 class="text-xl md:text-2xl font-bold mt-8 mb-3 text-gray-800">Core Responsibilities:</h3><ul class="list-disc list-inside my-5 pl-5 space-y-2 text-gray-700"><li class="leading-relaxed">Train and refine LLM-powered support systems to improve accuracy, empathy, and resolution rates. Use AI output and metrics to guide improvements to continuously refine LLM training data and prompts.</li><li class="leading-relaxed">Translate product functionality into LLM-ready documentation and prompts, ensuring launches are reflected in both agent resources and AI systems. Maintain ongoing documentation so it’s reliable, scalable, and optimized for LLM comprehension.</li><li class="leading-relaxed">Audit and test AI-driven support flows, experimenting with improvements that boost automation and customer satisfaction.</li><li class="leading-relaxed">Contribute to and shape the AI enablement strategy for CX systems, setting the approach for how AI and documentation work together to support customers and agents.</li></ul><h3 class="text-xl md:text-2xl font-bold mt-8 mb-3 text-gray-800">What Success Looks Like:</h3><ul class="list-disc list-inside my-5 pl-5 space-y-2 text-gray-700"><li class="leading-relaxed">AI resolution, satisfaction, and utilization rates steadily improve.</li><li class="leading-relaxed">Product launches are consistently supported by accurate, AI-ready documentation.</li><li class="leading-relaxed">Agents and customers trust LLM-powered support to provide clear, reliable answers.</li><li class="leading-relaxed">AI systems and documentation stay accurate and effective through regular tuning and iteration.</li></ul><h3 class="text-xl md:text-2xl font-bold mt-8 mb-3 text-gray-800">Skills & Experience:</h3><ul class="list-disc list-inside my-5 pl-5 space-y-2 text-gray-700"><li class="leading-relaxed">Clear writing ability to make complex information easy to understand</li><li class="leading-relaxed">Strong attention to detail and accuracy</li><li class="leading-relaxed">Independent, self-starter mindset with initiative</li><li class="leading-relaxed">Curiosity and enthusiasm for AI/LLMs, with a drive to learn quickly</li><li class="leading-relaxed">Customer empathy and strong people skills</li></ul><p class="my-4 text-gray-700 leading-relaxed"><em>The anticipated annual salary for this position is $70,000-$95,000.</em></p><h4 class="text-lg md:text-xl font-semibold mt-6 mb-2 text-gray-800">Outschool Cares:</h4><p class="my-4 text-gray-700 leading-relaxed">At Outschool, we believe that taking care of one another enables us to do our best work. To us that means:</p><ul class="list-disc list-inside my-5 pl-5 space-y-2 text-gray-700"><li class="leading-relaxed"><strong>Shared Financial Success:</strong> Competitive salaries, stock options, and investment plans that make saving for retirement easier.</li><li class="leading-relaxed"><strong>Health & Wellness:</strong> 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.</li><li class="leading-relaxed"><strong>PTO & Family Benefits:</strong> PTO and family leave enable our team to take the time that we need to recharge, relax, and spend time with family and friends.</li><li class="leading-relaxed"><strong>Fully Distributed:</strong> We create a remote culture through expensable meals, virtual events, expensable home office setup, and internet allowance.</li><li class="leading-relaxed"><strong>Lifelong Learners:</strong> 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!</li><li class="leading-relaxed"><strong>Community Impact:</strong> Outschool matches employee donations to established charities and has committed to support <a href="http://outschool.org/" target="_blank" rel="noopener noreferrer" class="text-blue-600 hover:text-blue-800 hover:underline transition-colors duration-200">Outschool.org</a></li></ul><p class="my-4 text-gray-700 leading-relaxed">’s non-profit programs.</p><p class="my-4 text-gray-700 leading-relaxed">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.</p><p class="my-4 text-gray-700 leading-relaxed">If you require a reasonable accommodation to participate in the job application or interview process, please contact <a href="mailto:recruiting@outschool.com" target="_blank" rel="noopener noreferrer" class="text-blue-600 hover:text-blue-800 hover:underline transition-colors duration-200">recruiting@outschool.com</a>.</p><p class="my-4 text-gray-700 leading-relaxed"><em>Benefits packages are included for full-time employees only.</em> <em>Please note benefits and perks may vary for employees based outside of the US and Canada.</em></p><p class="my-4 text-gray-700 leading-relaxed"><em>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.</em></p><p class="my-4 text-gray-700 leading-relaxed"><em>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 <a href="https://outschool.com/pages/privacy-Emp" target="</em>blank" rel="noopener noreferrer" class="text-blue-600 hover:text-blue-800 hover:underline transition-colors duration-200">Employee/Applicant Privacy Notice</a> 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._</p>

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