Transforming the system while it’s still running.

Oracle Expenses was one of four products chosen to lead Oracle’s next-generation design shift, picked for its reach: more than 100,000 people across 369 companies. In one interview, an administrative assistant told us she didn’t know what half the receipts were for, so she’d google it or go back and ask. That friction showed up everywhere.

I started as the only designer and grew the group to five designers, a creative technologist, and a research partner. We worked on two tracks at once, keeping the live product healthy while building the next one. On the live product, I designed hands-on alongside the team as we cut navigation from 26 entry points to 18 and added in-line and batch editing, and I worked directly with Oracle’s compliance team to drop requirements that slowed people down, like a written description for every taxi ride. For the next generation, built on Redwood, I designed and directed automation across submission, approval, and real-time machine-learning audit. That work produced two granted patents and was featured in the Oracle OpenWorld 2019 keynote.

Some AP teams were keying in as many as 30,000 invoices a month, about 65 per clerk per day at three minutes each. Telemetry showed 70% of specialists left the old landing page right after logging in. I led four designers and a researcher, ran weekly workshops so the team could learn AP from the experts, and we interviewed 17 specialists to find out what the tool was missing.

I directed the rebuild of the landing page into a hub, designing alongside the team, with prioritized work queues, faceted search, analytics, and quick actions, and invoices matched to a purchase order now fill themselves in. Manual entry time dropped by half. I also pushed to redesign the invoice itself, which reaches 1.7 million customers a year, as a low-cost way to put Redwood in front of all of them. The expense emails got the same treatment, since everyone at Oracle saw them.

Most of Oracle’s products were still being built feature by feature, and the complexity showed. At the SVP of Design’s request, I spearheaded an effort to change that, ran it, and recruited a small group to work with me. Together we created a two-part framework that has teams define the user’s goal and what success looks like before anyone designs a screen. I co-presented it live to more than 1,000 designers, PMs, and engineers, then ran working sessions and office hours with 18+ product teams who wanted to go deeper. Its patterns fed into the Redwood design system, and the framework still lives publicly on Oracle’s Clarity of Purpose site.

It changed how teams talked to each other. As one designer put it, having user goals in a crit “shifts the focus from ‘I don’t like that’ to ‘that’s not achieving the goal.’”

Redwood was Oracle’s next-generation experience and brand design system, and the most visible piece of a company-wide renewal. It started from a simple belief that enterprise users are people, and the tools they use at work should feel as easy and enjoyable as the apps on their phones. Oracle’s existing UX stretched a few patterns across too many scenarios, gave rare advanced tasks the same weight as everyday ones, and looked dated next to modern mobile. Redwood took all of that on across brand, marketing, sales, physical spaces and product UI.

My small team helped shape Redwood’s early direction. I art-directed and helped draw the storyboards the branding team used as a starting point for the look that followed, with its warm red and chocolate brown, the custom Oracle Sans typeface, and textures drawn from data. I also worked closely with the components team on many of Redwood’s interaction patterns, from larger pieces like interaction panels down to details like reordering the fields in the currency selector so they matched how people already think about entering money. Redwood debuted at OpenWorld 2019 and became the foundation for flagship experiences including Expenses, HR, procurement and oracle.com.