Caring.com

Caring.com was started in 2007 by Andy Cohen and two co-founders after caring for his mother through terminal cancer and finding no single place that told a family what to do next. By 2009 it had a caregiver resource center, a directory for assisted living and home care, and a growing community. It also had the problem every content startup gets at that stage: a lot of good features that had each been built on their own, so the site felt like six sites. I came in as the first senior design hire to fix that without stopping the company to do it. The company closed a $10M Series B that November, while the rebuild was already underway.

A redesign without a launch day

The obvious move was a site-wide relaunch. It was also the wrong one: a relaunch takes a year, freezes the roadmap, and bets the company’s traffic on a single day. So we redesigned the whole site anyway, just not all at once. I built the style guide and the pattern library first, then rebuilt the product one piece at a time as features shipped in the normal sprint rhythm: the homepage, search, the provider listings, articles, the community, the emails. Halfway through, the company bought Gilbert Guide, a senior-housing directory, and that came into the same system too, instead of living as a seventh site. The homepage got the deepest rework, because that’s where a caregiver decides whether this site is for them; it became more personal to the person’s situation, and repeat visits went up. Fifteen months later every page had been redesigned and the site spoke one visual language, and nobody outside had to notice a relaunch, because there wasn’t one. In aggregate it was a redesign. It was just a de-risked one.

The audience

The person on the other end is a daughter in her fifties, at work, on her lunch break, trying to find memory care for her father in a town she doesn’t live in. Every design decision started there: fewer choices per screen, plain words, phone numbers you can find, and nothing that looks like it’s selling. The 2010 Alzheimer’s guidance tool, which walked a caregiver from symptoms to what to do next, was the clearest expression of that. Caring Candles was the other one: friends and relatives could light a candle for someone and leave a message on a wall for them. It sounds like a small thing to build. It ended up driving a ton of traffic and got itself a sponsor.

What the people there said

Sean Ross is an exceptionally talented and very disciplined designer with an eye for simple, easy-to-use interfaces and the ability to design towards a unified, consistent, and intelligible site experience while working on a disparate set of site components. At Caring.com, he arrived to a site whose feature set was excellent but highly silo-ed and was able, over the course of many different projects of varying size, to establish a much more consistently patterned UI and visual style, but without the cost, deliberation, and risk involved in a site-wide redesign. Sean is an intelligent and insightful participant in the process of product definition, one who cares about the big picture and the granular details. He is a responsive colleague who knows not just how to make things pretty but also how to get things done. And he’s frequently totally hilarious.

— Tim Sullivan, Director of Product Management, Monami

As a product manager, I need my creative director to be a lot of things: a great collaborator, understanding and interested in the customer, the application capabilities and the engineers; I need this person to be flexible, handle feedback well, listen and work off others’ ideas effectively, handle office dynamics well, and of course be the most creative guy in the room. Sean is all this and more. From mock ups to iterations to final design to working with the engineers on implementation, he does excellent work. He’s also a really wonderful guy. I would work with Sean again in a heartbeat.

— Laurel Lee, Senior Staff Product Manager, Plenty

Sean has a great creative eye and developed a consistent and better style guide in a short amount of time. His strong point of view is complemented by an ability to collaborate and a great sense of humor.

— AJ Kohn, Owner, Blind Five Year Old

Sean is a talented and capable designer, and did some great work for us at Caring.com. I’d definitely recommend him for design projects!

— Andy Cohen, founder and CEO, Caring.com

What happened

Caring.com kept growing on that system, took Intel Capital’s money in 2010, was a Webby Official Honoree and a Red Herring Top 100 company in 2013, after my time, and was acquired by Bankrate in 2014 for $54 million. It’s still running; it changed hands again in January 2026. The lesson I use most from it: a design system is a way to redesign a product without anyone having to approve a redesign.