In order to best visualize our merchants without using photography, I developed a couple of libraries/systems/tools to draw people. I created them as tools to better serve our designer base so that I'm not the only person who can execute. We use these in product, email, and web.
Following are samples made using the portrait tool.
Portraits sometimes can feel too detailed. For instances where simplicity and scale are needed, I've devised a tool to build people at a smaller scale that works in the same way as the portrait builder.
Buildings are a great way to represent businesses and merchants. By building out a series of building which are inhabit the same universe, it is easy to mix and match to create the scene that best represents the higher concept.
All Hands Deck Covers
This project is an ongoing collaboration with Square's Comms Design team. We designed a new deck for the company all hands. My cover illustrations demonstrate how Square's products live in the real world in abstract ways. Each cover represents a different season, which we then switch quarterly. Summer, Autumn, Winter, with Spring coming soon.
Tools in practice
I built out our illustration library to be easily editable. The tools I've created have been used by other teams to create work which mimics my style. Because of this, I am able to build tools instead of making dozens of one-off illustrations. By empowering other designers, we make better work.
The Caviar engineering and design teams took my illustrations, made a couple of their own, and built this interactive game for the 404 page.