CloudWatch Application Insights was expanding its monitoring capability to support complex enterprise applications with multiple workloads, such as Java and SQL applications running across EC2 environments. The initial product request was to add more form fields to an existing single-workload onboarding flow, but the setup experience already had significant friction, with a 57% drop-off from Step 2 to Step 3 and another 10% drop before completion.

As UX Designer, I reframed the work from a UI addition into a broader onboarding redesign. I conducted a heuristic evaluation, analyzed Darkroom data to identify drop-off patterns, and used the findings to align Product and Engineering on the need for a more customer-centered setup flow. I also ran user testing to understand customer mental models, collaborated with the CloudWatch team to align with its design language, and tested different messaging approaches around workload detection failures.

The redesigned onboarding experience launched with multi-workload support and improved setup clarity for complex monitoring use cases. Within two months, Step 2 completion increased by 16%, with around 2,500 users interacting with the flow bi-monthly. The work helped the team move beyond “adding fields” toward deeper CX thinking, and led to earlier UX involvement in CWAI’s 3-year vision, including GenAI, Console One, EC2, and AWS Cost Optimizer integrations.