Learning & Enablement Lead - Product Adoption & Training

City Wide Property Services, Inc.; California (MO); On-site; USD 110,000 - 150,000; Full time

Job summary

City Wide Property Services, Inc. is seeking a Product Specialist to own and continuously improve the end-to-end learning experience across City Wide Plus+ and its applications.

You will design learning journeys for field employees, managers, and clients, and establish standards, certifications, and governance for training. You will collaborate with Product, Engineering, Operations, Client Success, and Leadership, creating multimedia content, SOPs, onboarding programs, and data-driven enablement

Qualifications

• The ideal candidate is passionate about education, process improvement, technology adoption, and leveraging AI-powered tools to deliver impactful learning experiences that support organizational growth and operational excellence.

Responsibilities

• Own and continuously improve the end-to-end training and learning experience within City Wide Plus+.
• Design role-based learning journeys tailored to field employees, coordinators, managers, executives, vendors, and clients.
• Establish training standards, certification paths, completion tracking, and content governance frameworks.
• Leverage AI-driven learning tools and analytics to increase engagement, adoption, and knowledge retention.
• Develop scalable training programs aligned with business processes, workflows, and operational best practices.
• Create and maintain SOPs, process documentation, job aids, knowledge base articles, assessments, and reference materials.
• Partner with business stakeholders to ensure documentation remains accurate as platform capabilities evolve.
• Build and manage a centralized knowledge ecosystem that supports self-service learning and operational consistency.
• Design, produce, and maintain engaging training content including videos, tutorials, walkthroughs, simulations, and micro-learning modules.
• Script, record, edit, and publish role-based product training and workflow demonstrations.
• Apply instructional design methodologies and adult learning principles to maximize adoption, usability, and retention.
• Utilize AI-powered content creation tools to streamline training development and updates.
• Lead training initiatives that support new product releases, workflow changes, and operational improvements.
• Deliver live workshops, webinars, office hours, and hands-on learning sessions.
• Develop change management and reinforcement strategies to drive user adoption and process compliance.
• Monitor training effectiveness and identify opportunities for continuous improvement through user feedback and analytics.
• Design and deliver scalable onboarding experiences for new City Wide Plus+ clients.
• Create guided product adoption programs, embedded learning experiences, and self-service training resources.
• Partner with Client Success teams to improve activation, adoption, retention, and overall customer experience.
• Develop training strategies that help clients maximize platform value and operational efficiency.
• Collaborate closely with Product, Engineering, Operations, Marketing, and Client Success teams to support platform adoption initiatives.
• Translate user feedback, training insights, and adoption metrics into recommendations for product enhancements.
• Support user acceptance testing (UAT), release readiness, communication plans, and feature rollout strategies.
• Help define and implement native training, onboarding, AI assistance, and enablement capabilities within City Wide Plus+.
• Track training completion, adoption trends, user engagement, and knowledge gaps.
• Develop metrics and reporting to measure the effectiveness of training programs and enablement initiatives.
• Use data-driven insights to optimize learning experiences, improve operational performance, and increase product utilization.
• Identify opportunities to automate, personalize, and scale learning through AI and modern enablement technologies.

Job description

City Wide Property Services, Inc. is seeking a Product Specialist to own and continuously improve the end-to-end learning experience across City Wide Plus+ and its applications.

You will design learning journeys for field employees, managers, and clients, and establish standards, certifications, and governance for training. You will collaborate with Product, Engineering, Operations, Client Success, and Leadership, creating multimedia content, SOPs, onboarding programs, and data-driven enablement