My work is mostly under NDA currently. Can I send links to Flintos/Layervault?

Totally, just explain that in your application.

Also, how does the trial process typically work?

First off, it's a paid trial. You'll be working one-on-one with the designer in charge of hiring on a product-related project. It typically involves doing a round of research, sketches or wireframes, higher fidelity mockups of some kind, and then an html/css/js optional prototype. Throughout each round you'll present your work and your decisions and receive feedback.

Designers are integrated into project teams. For the most part, there's only one designer per team (some teams are gaining second designers now as we grow). Most of our collaboration happens via a slack channel for design, and our internal design blog. We try to collaborate or ask for feedback pretty frequently.

Our schedules are very flexible. Since we are international, we have people working pretty much whenever. Most people opt to work during the regular workday wherever they are (9-5, or in my case, generally 10-6), but there's opportunity to flip around your schedule to suit your working habits, as long as it doesn't negatively interfere with your ability to get your work done.

Automattic is always hiring UI Designers: http://automattic.com/work-with-us/user-interface-designer/

The job's a little different depending on the team you join, but the job description is a good indicator of what we're looking for. Happy to answer any questions about the application/trial process and what it's like being a designer at Automattic.

Plus, we're remote, so you can work from anywhere. :)

The site is using WordPress.com, so there's not really a great way to add the text over the featured image without putting it in the image itself.