Learning & Enablement Specialist (AI & Automation) -100% Remote

Company Description: Hyly.AI is the multifamily industry’s premier Intelligence Fabric™, integrating Artificial, Business, and Human Intelligence into a single system designed to drive operational growth. By transforming raw data into actionable decisions and measurable results, Hyly.AI enables scalable operations without the need for additional resources. Founded in 2010, Hyly.AI has over a decade of experience in simplifying complex processes for multifamily leaders, helping them optimize efficiency and increase ROI. Trusted by 4 out of the top 5 NMHC managers, Hyly.AI empowers teams to focus on building meaningful communities rather than handling repetitive, manual tasks.

Role Description: What You'll Do You'll own learning systems that scale knowledge across Sales and CSM teams. This isn't about scheduling training sessions - it's about building AI-powered infrastructure that identifies gaps, creates assets proactively and makes learning self-service. Manage & Evolve S.Academy (Hyly's AI-Powered LMS).

Job Responsibilities:

Manage & Evolve S.Academy (Hyly's AI-Powered LMS) Maintain current operations: Ensure courses run smoothly, troubleshoot issues, and support learners in real-time Drive Phase 2 evolution: Build the admin interface, create AI-generated tutorials, and develop self-service capabilities for team-created courses Target: Q4 2026 - S.Academy becomes the single source of truth for product and process learning, with 80% reduction in manual L&D intervention

Proactive Knowledge Asset Creation (Client-Facing Teams) Proactively create and refresh client-facing enablement assets for Sales, CSM, Support, and Marketing Build assets in multiple formats based on real questions and upcoming launches: ◦ Refresher courses (S.Academy modules) ◦ Interactive demos (Storylane or similar) ◦ Quick tips (micro-learning, job aids, talk tracks) Use automation (Notion AI agents, n8n workflows) to detect recurring questions and product changes, then generate draft updates Maintain a lightweight prioritization model based on client impact, ticket volume, etc. AI-Powered Learning Automations Create Notion AI agents that generate first drafts of standard assets (FAQs, process guides, quick reference cards) Develop AI-assisted content templates that reduce asset creation time by 50% Knowledge Asset Creation Write clear, actionable knowledge base articles, integration guides, and process documentation Design learning experiences (courses, workshops, self-guided materials) for CSM and Sales teams Maintain and update existing assets to reflect product changes and evolving team needs L&D Best Practices Research Stay current on learning science, instructional design, and AI-enabled education trends Test new tools and approaches (AI tutors, adaptive learning, microlearning platforms) Apply research findings to continuously improve S.Academy and Hyly's learning ecosystem

Must-Have Qualifications:

5+ Years Learning & Development Experience Proven track record supporting Sales and/or Customer Success teams specifically Experience managing an LMS and driving the adoption of learning systems Portfolio demonstrating successful proactive knowledge asset creation → adoption → measurable improvement cycles Advanced AI Fluency (4/5 Minimum) Claude: Skilled with Projects, extended conversations, and Artifacts for content generation ChatGPT: Proficient with custom GPTs and advanced prompt engineering Perplexity & Gemini: Comfortable using for research and knowledge synthesis You should be comfortable designing AI workflows, not just using pre-built tools LMS Management Experience Hands-on experience administering and evolving a learning management system Comfort with both the learner experience and the technical/admin backend Bonus: Experience building AI-enhanced learning platforms Education: Bachelor's Degree, 3.2+ GPA Demonstrates strong foundational learning ability and discipline • Relevant fields: Instructional Design, Education, Psychology, Communications, or related

Preferred (Nice-to-Have) Qualifications: n8n automation experience: You've built workflows that connect systems and automate repetitive tasks Storylane or similar demo tools: You can create polished product walkthroughs and interactive demos Python or JavaScript coding knowledge: You can read/modify scripts to customize automations and learning tools