Brought SysAid's first self-serve Advanced trial to a traditionally sales-led product

SysAid is an enterprise ITSM platform that has grown entirely through direct sales for its whole history. Every new customer started with a sales conversation, a demo, and a procurement cycle. The product had never had to make a first impression on its own.

License Manager Advanced is a module within SysAid that discovers SaaS applications running across an organization and surfaces cost savings. The business wanted to introduce a PLS motion as a first step toward full PLG: a free 14-day trial that lets prospects evaluate the product autonomously, get to value on their own terms, and then make a qualified, informed call to sales. The immediate goal was self-serve evaluation, not self-serve conversion — but the longer-term direction is a fully product-led growth model.

The design problem was unusual: you can't interview trial users before they've used the product. There's no discovery phase with them. You design, you launch, and you watch what happens in the recordings.

I led design across three parallel workstreams: the trial start experience, the in-trial limitation UI, and the trial end and expiry experience. The core tension in all three was the same: the product's value is discovery. Finding SaaS applications your organization didn't know it was running. The trial had to demonstrate that value clearly without giving it away fully. Show enough to create urgency; not so much that there's no reason to upgrade.

The harder part of the job wasn't the UI. Sales needed to believe the trial wouldn't bypass them: it would generate better-qualified leads, not self-serve conversions that skipped the conversation entirely. That required showing the sales team the design logic: the trial reveals the problem, but sales closes the solution. Aligning marketing on who the trial was targeting, and what message prospects would arrive with, was a major workstream alongside the product design itself.

Getting users to connect their environment is step one. Getting them to enrich the data (adding license counts, cost information, and reviewing discovered apps) is what actually makes the product valuable during the trial window. We used UserFlow to bridge that gap without requiring a support rep or onboarding call.

Once the application scan completes and the user lands on the Applications table, UserFlow triggers a contextual tooltip: "Your applications are ready. Discover how to manage your applications and optimize costs with a brief 1-minute walkthrough." The user can accept or dismiss. If they accept, a guided side panel walks them through the remaining enrichment steps in sequence, with contextual tooltips pointing to the exact fields they need to fill in.

The design logic: the more data a user puts into License Manager during the trial, the more accurate their savings estimate, and the stronger the upgrade case. UserFlow was the mechanism for nudging users toward that enrichment at the right moment, with the right framing, without interrupting the core experience.

Traditional user research requires access to users before they experience the product: interviews, usability tests, observation sessions. For a trial, that's impossible. The trial IS the first experience. There's no one to interview before it exists.

The primary research tool was session recordings: watching real trial users navigate the product after launch. Where they hesitated. Where they dropped off. What they actually clicked versus what the design expected them to click. Every recording session fed directly into the next design decision.

This constraint shaped the design philosophy. Build something that works before you fully understand the user, then iterate fast on what you see. The post-launch feedback cycle was part of the design process from the start, not an afterthought added once the product was live.