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.About The Role:
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.
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.
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.
Core Responsibilities:
- 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.
- 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.
- Audit and test AI-driven support flows, experimenting with improvements that boost automation and customer satisfaction.
- 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.
What Success Looks Like:
- AI resolution, satisfaction, and utilization rates steadily improve.
- Product launches are consistently supported by accurate, AI-ready documentation.
- Agents and customers trust LLM-powered support to provide clear, reliable answers.
- AI systems and documentation stay accurate and effective through regular tuning and iteration.
Skills & Experience:
- Clear writing ability to make complex information easy to understand
- Strong attention to detail and accuracy
- Independent, self-starter mindset with initiative
- Curiosity and enthusiasm for AI/LLMs, with a drive to learn quickly
- Customer empathy and strong people skills
Outschool recruits across the US and Canada, and sets employee salaries to reflect local compensation and cost of living. The anticipated annual salary for this position is $70,000-$95,000.
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.
- 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.
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