Leading an Enterprise Training & Enablement Initiative

I identified critical training gaps, advocated for technical enablement resources, and established a dedicated onboarding team that shipped a new LMS in under three months.

Challenge

I was the product designer for a feature-heavy CMS application, working within a program of 10+ product teams all assigned to different enterprise applications. My CMS application had a steep learning curve with complex workflows, creating barriers to user success in a high-stakes government environment with real human downstream impacts. Despite consistently shipping new features and improvements, we were experiencing low adoption rates for new functionality.

Even more concerning, users were repeatedly requesting features that we had already shipped. This pattern suggested a fundamental disconnect between our development efforts and user awareness, indicating that our feature-heavy CMS application wasn't effectively communicating its evolving capabilities to users in a high-stakes government environment with real human downstream impacts.

Insight

Through user feedback and engagement analysis, I hypothesized that the core issue wasn't with our features themselves, but with insufficient training and communication surrounding new feature launches.

Key findings revealed:

• Low engagement with announcements: Teams and email notifications about new features had poor open and engagement rates
• Information overload: Users admitted they couldn't keep up with the constant stream of feature announcements across all applications
• Communication fatigue: Users had stopped reading their emails about product updates entirely

The rapid pace of development across 10+ product teams meant users were constantly receiving updates and improvements, but had no effective way to stay informed about changes that directly impacted their daily workflows.

First-slice Solution

To test our hypothesis about technical enablement, we developed a super lean solution that we could ship quickly and measure immediately. We added a dismissible notification bubble directly in our application interface to point out a new feature, which linked to a job aid that I created.

This minimal viable solution was designed to:

• Catch users' attention within their existing workflow
• Provide contextual information exactly when and where they needed it
• Link to practical guidance they could reference immediately if desired

We shipped this solution within a week and immediately saw increased interactions with the new feature, validating our approach to in-application guidance and contextual training materials.

Opportunity

Armed with this successful proof-of-concept and compelling data, we expanded our research to understand the full scope of the problem. I gathered historical adoption metrics for previously shipped features and compiled user quotes and survey requests that illustrated widespread lack of user awareness across the program.

I pitched program leadership and stakeholders on a comprehensive suite of onboarding and technical enablement tools. Our proposed approach was to:

• Use our CMS application as a pilot to develop scalable, modular training components
• Ship solutions incrementally and measure success at each step
• Distribute proven techniques and reusable components to the other 10+ product teams
• Foster cooperative efforts between technical product teams and the business's internal training teams

Business investment

Our pitch was so successful that instead of limiting the initiative to piloting with the CMS product, the client decided to invest fully in a dedicated technical enablement team to work across 10+ product teams. The business recognized the strategic value of my insights and dedicated resources specifically to this initiative.

Rather than starting small with one application, client leadership wholeheartedly accepted the broader vision. I was selected as the founding designer for this new team and immediately dove into a three-month discovery and framing period to investigate program-wide training challenges, moving beyond my previous application focus.

User Research

During the comprehensive discovery phase, I conducted 22 user interviews with stakeholders, end users in different roles, and supervisors. This research revealed that training gaps extended far beyond feature awareness—the problems were systemic and deeply embedded in how the organization approached user enablement.

Key Research Findings

Trainers lacked technical confidence: For various reasons, trainers were not comfortable with the technology and could not effectively train users on the case management system and other essential enterprise applications.

Problematic staging environment: The staging environment used for training was incredibly difficult to use for both trainers and trainees. Trainees often arrived at training sessions only to discover they couldn't access the staging environment at all.

Incomplete training scenarios: The staging environment lacked the ability to take a case through its entire lifecycle, forcing trainers to make do with imperfect cases when demonstrating essential job functions.

Systemic training gaps: The problems went beyond just feature awareness—trainers were struggling to effectively instruct users on the suite of enterprise applications that were essential to their daily jobs.

Solution

Based on our research findings, we designed and shipped a functional and scalable Learning Management System in three months that addressed each major pain point we had identified.

The LMS enables trainers to:

Create and manage classrooms with dedicated training environments

Verify learner access to crucial systems before training begins

Assign realistic practice cases that could be taken through complete workflows

Manage assignments and track trainee progress through essential job functions

Key Features

Classroom Management: Streamlined interface for trainers to organize and manage training cohorts

Access Verification: Built-in tools to ensure trainees can access necessary systems before training sessions begin

Custom Staging Case Templates: Practice cases designed to demonstrate full workflows and essential job functions at the click of a button

Assignment Tracking: Progress monitoring tools for both trainers and supervisors

Learner Portal: Simple, streamlined way for learners to access their classrooms and assignments

Impact

Leading this strategic initiative demonstrated the power of identifying systemic problems and advocating for comprehensive solutions at the organizational level. What began as diagnosing adoption issues for a single application ultimately resulted in transforming how the entire program approaches user enablement.

Key achievements:

Successfully pitched leadership to create an entirely new product team from a single application insight

Established scalable training infrastructure serving 10+ cross-functional teams

Delivered a working LMS in just 3 months that addressed core training challenges

Created sustainable frameworks for ongoing technical enablement across the program

Improved trainer confidence and effectiveness through better tools and environments

This project demonstrated my ability to identify problems at the product level, validate solutions through rapid experimentation, and scale insights into organizational change that addresses systemic challenges across complex enterprise environments.