[All remote jobs](https://jobicy.com/jobs.md)[![Superside logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/01/WRILS-210104060359-501693.jpg)](https://jobicy.com/company/superside.md)[Superside](https://jobicy.com/company/superside.md) # AI Enablement and Learning Specialist Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/superside.md)ShareRemote from[EMEA](https://jobicy.com/job-region/emea.md)SalaryUndisclosedDepartment[Education & E-learning](https://jobicy.com/categories/education.md)EmploymentContractExperienceSeniorPublished20 Oct 2026Apply before19 Nov 2026Listing views34Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Superside is hiring a contractor to build AI-enabled learning operations and practical enablement solutions for a distributed workforce. The role combines learning experience design, knowledge management, LMS administration, workflow automation, and experimentation with Claude-supported resources. The specialist will independently turn ambiguous learning goals into scalable onboarding, content, reporting, and knowledge solutions. Success depends on strong systems thinking, technical curiosity, clear asynchronous writing, and stakeholder partnership across the company. This is a remote EMEA role in a fast-paced, high-trust environment. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 4/5IndependentCollaborative AI insightThe position requires independently translating broad learning objectives into reliable AI and automation workflows while maintaining usable knowledge systems. It demands both learner-centered judgment and enough technical fluency to prototype, launch, and improve cross-functional solutions. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$85,000US market range (per year)$65k–$110k0$121.00k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No employer compensation is disclosed. The displayed figures are estimated annual USD market compensation for a mid-level to senior AI-enabled learning and enablement specialist working remotely in EMEA; the annual cadence is inferred from the professional contractor role context. ## Core skills Skills and capabilities most closely associated with this opportunity. [Learning enablement](https://jobicy.com/jobs?search_keywords=Learning%20enablement.md)[Knowledge management](https://jobicy.com/jobs?search_keywords=Knowledge%20management.md)[Artificial intelligence](https://jobicy.com/jobs?search_keywords=Artificial%20intelligence.md)[Claude](https://jobicy.com/jobs?search_keywords=Claude.md)[Workflow automation](https://jobicy.com/jobs?search_keywords=Workflow%20automation.md)[Learning management systems](https://jobicy.com/jobs?search_keywords=Learning%20management%20systems.md)[Sana LMS](https://jobicy.com/jobs?search_keywords=Sana%20LMS.md)[Notion](https://jobicy.com/jobs?search_keywords=Notion.md)[Asynchronous onboarding](https://jobicy.com/jobs?search_keywords=Asynchronous%20onboarding.md)[Instructional design](https://jobicy.com/jobs?search_keywords=Instructional%20design.md)[Learning content development](https://jobicy.com/jobs?search_keywords=Learning%20content%20development.md)[Process improvement](https://jobicy.com/jobs?search_keywords=Process%20improvement.md)[Stakeholder management](https://jobicy.com/jobs?search_keywords=Stakeholder%20management.md)[Technical troubleshooting](https://jobicy.com/jobs?search_keywords=Technical%20troubleshooting.md)[Written communication](https://jobicy.com/jobs?search_keywords=Written%20communication.md) Sample interview questionsHow would you evaluate an AI-powered learning idea before investing in a full implementation?I would define the learner problem, intended outcome, audience, risks, and success metrics first. I would then build a small prototype, test it with representative users, assess quality and reliability, and compare the measured benefit against maintenance effort before scaling it. Describe how you would improve a fragmented learning knowledge base. I would audit the existing content for ownership, accuracy, duplication, audience, and usage. Then I would create a clear information architecture, define templates and governance, assign content owners and review dates, and use search-friendly naming and links so people can find trusted information quickly. How would you automate onboarding in an async-first company? I would map the new-joiner journey and identify repeatable triggers such as a start date, team assignment, or system access. I would automate enrolments, timed reminders, progress tracking, and manager notifications while retaining clear human escalation paths for exceptions and questions. What safeguards would you use when creating Claude-supported learning resources? I would set clear use cases, provide approved source material, avoid exposing sensitive information, and establish review criteria for accuracy, tone, and bias. I would also document prompt patterns, monitor user feedback, and keep a human review step for material that affects policy, compliance, or critical decisions. How do you manage priorities when stakeholders have competing learning requests? I clarify the business outcome, learner impact, urgency, scope, dependencies, and expected effort for each request. I make trade-offs visible through a prioritization framework, align on the highest-value work, and communicate delivery expectations and alternatives early in writing. Opportunity details ## About this role. Superside is reinventing how its people learn, and we’re looking for someone to help bring that vision to life in practical, AI-powered ways. As an AI Enablement and Learning Specialist, you’ll join the Learning Enablement and Transformation team. You’ll work closely with the person leading our learning strategy, turning goals and ideas into working solutions: Claude-supported resources, automated workflows, and well-organized knowledge that people can actually find and use. You’ll also keep the systems and knowledge behind our learning programs in good order, so everything runs smoothly with little manual effort. This isn’t a traditional L&D role. If you love working with information, enjoy building with AI and automation tools, and care about how people learn, you’ll feel at home here. You’ll work independently, from ideas and open problems rather than step-by-step briefs, in a fully remote, ambitious, async-first team. ### What you’ll do * Research practical, AI-powered ways to deliver on our learning goals, and recommend what’s worth implementing. * Prototype Claude-supported learning resources and automations, and turn the best ones into working solutions. * Build and launch new learning initiatives, from first idea to something people use. * Run and improve async onboarding, so new joiners get a smooth, mostly automated experience. * Organize and maintain our learning knowledge, so it’s easy to find, trust and keep up to date. * Automate enrolments, reminders, tracking and reporting across our learning systems. * Look after our learning systems and tools such as Sana LMS, Notion, Claude so they stay reliable and easy to use. * Create learning content when needed, such as short modules, guides and resources. * Work with stakeholders across the company to understand their learning needs and turn them into practical solutions. ### What you’ll need to succeed * Strong experience organizing and managing knowledge: structuring information, keeping it current, and making it easy to use. * Hands-on experience building with AI, and a real curiosity about what’s possible next. * Experience with workflow automation tools and a comfort with the technical side of things. * A systems mindset: you see how the pieces connect, and you follow through until it works. * Comfort solving problems from ambiguity, turning an idea or a rough goal into a clear plan. * A people-first approach: you think about the learner and their experience, not just the tool. * Experience in learning and development, HR, enablement, or a related field is a plus, though it’s not the centre of the role. * Experience with learning platforms (such as an LMS) is a plus. * Ability to create clear, simple learning content and communications. * Proactive and independent: you don’t wait for step-by-step instructions. * Great written communication in English, and comfort working async in a remote team. ### Compensation ### Additional Information Why Join us? Superside’s vision is to create equal opportunities globally by accelerating the world’s transition to online work. With that in mind, we’re building a fully remote company that attracts people where they are. Remote-first. Customer-led. Remote isn’t just a perk; it’s how we deliver better for customers. We are fully committing to our customers by hiring top talent and collaborating seamlessly across time zones. Global team, local impact. Join a community of 60+ nationalities working across time zones, cultures, and disciplines, all aligned on doing great work for great brands. High performance, low ego. Work in a fast-paced, high-trust environment where feedback is direct, growth is constant, and kindness leads collaboration. Impact meets opportunity. We’re in the sweet spot — big enough to be stable, small enough for you to shape what’s next. Your ideas will matter here. Grow fast. Lead well. You’ll gain mentorship, take on real responsibility, and grow your career while helping us disrupt a global industry. About Superside Superside is the leading AI-powered creative company that quickly and cost-effectively enhances in-house functions. We help over 500 ambitious brands get great creative concepts done at scale. Built to be an extension of in-house teams, we unbottleneck marketing and creative teams so they can move faster and drive more reliable creative performance. Superside is a fully remote company with over 700 team members working across 60+ countries and 13 timezones. Learn more at [superside.com](http://superside.com) Diversity, Equity and Inclusion We’re an equal-opportunity company. All applicants will be considered regardless of ethnicity, appearance, religion, gender identity, sexual orientation, national origin, veteran or disability status. Show more [Apply now >](https://jobicy.com/jobs/156074-ai-enablement-and-learning-specialist.md) > Annual salary information is not provided for this position. 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