About

Design Outcomes is the working notebook of a Design Executive in practice. I'm Leonardo De La Rocha, and this site is where I publish the actual work of running a design organization, in real time, in two formats.

Articles run long. Full-length pieces on the decisions, the frameworks that survived contact with reality, and the tradeoffs that turn out harder than they looked on paper. The work I want to think through carefully and put on the record.

Field Notes run short. Annotated reads on the tactics other teams are getting right, with notes on what makes them worth studying. The kind of entry you'd find scribbled in the margin of a real notebook.

The goal is to share the practice openly, in the moment, without the distance of polish. No sponsors. No popovers. Just the work.

The design itself is meant to be read, too. A quick tour.

The masthead "DO" logo tips its hat to Ben Barry, designer and co-founder of the Facebook Analog Research Lab, whose blackletter mark for that team set a bar for what a design org's flag could look like. Mine borrows the spirit of that work.

Hero illustrations are drawn in a Risograph style: two inks on cream paper, with all the registration drift, edge wear, and pinhole specks the medium asks for. Each one is bespoke to the article it announces. The cover should argue for the piece, not just decorate it.

The articles carousel cycles through them the way a Riso ticks through prints, one sheet at a time.

Field Notes (the section) is a wink at Field Notes (the notebook). Each card is a pocket notebook, kraft band and all, the kind of object that ends up creased in a back pocket and weirdly indispensable.

The cream background is the paper. Italic serif headlines come from editorial print. All-caps sans labels come from broadsheets and gig posters. Letterpress thinking, rendered in pixels.

I'm an engineer turned designer turned design executive, roughly thirty years in, starting with graffiti and lettering in Denver and winding through Yahoo, Facebook, Intuit, Spotify, and now SimplePractice, where I'm VP of Product Design.

At SimplePractice, I lead a thirty-person design organization building the EHR platform that over 250,000 independent behavioral health clinicians use to run their practices. The work spans clinical care, revenue cycle, mobile, and an emerging AI practice. The clinicians we serve are mostly solo or small-group, which keeps the bar high: their software has to be the kind of thing one person can run a business on.

Before this, I led design for Spotify Advertising, a 64-person organization across product design, research, content design, and program management. Before that, Intuit's design system and accessibility work across TurboTax, QuickBooks, ProConnect, and Mint. And at Facebook, Creative Director for Studio X (the in-house creative team for business products) and Product Design Manager for the ads platform. The ads team was called Outcomes. I've never stopped liking that name.

A few principles I've carried across every role. Help people grow, not just finish tasks. Save time without losing sight of what people are using the tool for. Bring clarity to complex tools without flattening them. Be reliable in the way organizations actually need: predictable enough to plan around.

Outside the day job, I take freelance branding and illustration work to keep a hand in the craft, mentor on ADPList, and speak on design leadership and AI's impact on design orgs. Most recently I keynoted Upscale Conf on how new AI input modalities are reshaping the way design teams work.

I believe design is a form of tuned awareness, that leadership is posture more than title, and that the surest way to build trust with a team is to show your work. This site is me showing mine.