Gusto Design: Evolving from designers to builders

This is the most comprehensive writeup I’ve seen yet documenting the challenges and successes of converting an entire design org to designing with AI.

Katie Kovalcin, Distinguished Designer, documents the transformation led by Gusto’s Chief Design Officer, Amy Thibodeau. So much resonates with the transformation (still underway) of our 40+ design team at Desquared: slow adoption when AI is treated as “nice to have”, designers having that “aha” moment when they ship their first PR, the CDO leading the charge with hands-on work, and much more.

After laying some of the scaffolding needed to unlock designing in AI,

Amy announced at our February design all hands that she wanted every designer to have fully transformed the way that they’re working by June 1 and for static Figma files to no longer be how we work.

There was understandably a lot of fear, uncertainty, and doubt from the design team, and some mixed feelings across R&D. Some engineers weren’t thrilled about designers being in the code and PMs were worried about moving away from a tool they had also come to rely on.

Designers were worried about how they would ensure the right experience guardrails were in place to get a good output from AI.

And yet just a few months later, the impact of this transformation was clear:

Suddenly, things were evolving at a rapid clip. It even started to feel… fun? We started to hear from designers that they now dreaded having to go back in and use Figma because they preferred this new way of working.

Fast-forward to today and (I suspect) Gusto is now trending ahead of many other design orgs. Consider what they’re doing with prototype collaboration: 

As a distributed team, being able to work together asynchronously is important to us and a meaningful limitation we still had. We closed this gap by having our AI Dev tooling team build out “shareable links” for our sandbox prototypes, so creating a PR for a prototype will give you a real link that you can send someone on your team to see your prototype.

This is a known issue across the industry. localhost is great but of course unshareable, resulting in video meets or screen recordings to share progress updates. Pointing peers to sandbox prototypes is an important unlock for designing with AI. Described later in the article is the custom commenting their team built on top of sandbox prototypes. 

I’m not done yet. There’s still more to call out.

Amy worked with our Design System leaders to reposition the team as “Builder Enablement” with a new formal mission dedicated to supporting [LLMs making good design decisions at scale] ... and extending things like the Sandbox environment, Workbench MCP, and more forward looking AI-designing workflows.

Oh, I love this. For the past decade design systems (and their teams) have largely been seen as tools of consistency and enforcement. Transitioning to teams of enablement is a brilliant path forward.

Then, there’s this:

As a designer, I was able to take on features that traditionally would have been labeled as “nice to have” and been cut for an MVP.

This is such a massive unlock. If you’ve not already fully immersed yourself in designing with AI, you will be thrilled to know that you can squeeze in work no one approved to prioritize in the roadmap, to say it bluntly. And when a fix or nice-to-have takes just 5 minutes to execute, no one will be the wiser. Correction: your users will be the wiser, for the better.

Lastly, it’s refreshing to see Katie’s perspective on craft matches mine: “Designer’s human judgement on craft is being replaced by AI,” she notes, “but using AI enables us to spend more of our time focused on where that judgement is best used.”

As a former user of Gusto at previous employers, I can vouch for what Gusto Design is doing to ship useful, delightful experiences. Brava, Amy & Katie.