Creating a content strategy out of whole cloth

Joel Edelman
Gusto Design
Published in
5 min readNov 30, 2021

This spring, Gusto made two key decisions. First, we tripled the size of our content design team. And although Gusto is known for awesome payroll, HR, and benefits features for small businesses, we knew that we have a lot to offer businesses of larger sizes too. As a result, we recently built an entire org to focus on them.

I am the intersection of these two movements. I am the content designer for experiences designed for companies with more than 25 employees. Hi!

Welcome to Gusto, Joel

It feels great to come into a company in this context, because everyone is so happy to see you, like you’re firefighters appearing on the scene of a 5-alarm blaze. Gusto had already seen tremendous success and was about to hit the 200,000-business mark, a substantial achievement for a company of 1,400 employees.

But you’re still showing up to a fire, and the expectant looks of your new coworkers (we call ourselves “Gusties”) tell you all the story you need: Do something, anything!

Let’s see what we’ve got

As I mentioned, much of the early design work at Gusto focused on smaller businesses, and when you’re designing for a 2-person company, there are certain design decisions you make to optimize for that. These same decisions may cause a 100-person company to struggle while interacting with your experience. This extends to the words you use.

I was pleasantly surprised when I began working for Gusto that there was some UX writing documentation as well as process notes sitting on a Google Drive. Not only was there some precedent, but it meant that there was some appetite to create order from the chaos.

For me this meant doing an audit of the resources already in place. This helped me understand the current content culture at Gusto, as well as identify opportunities to improve on it and adjust it for our new design work for larger companies.

Stuff to learn — and stuff to forget

One of the biggest challenges was to provide contrast between what our colleagues knew vs. what they needed to learn. For example, companies with more employees are more likely to have people in specialized roles. Understanding their technical acumen for the areas they work in would help us know the level of detail to provide.

What’s more, we could better guess the vernacular they would be comfortable with. It doesn’t mean it is OK to use jargon for no reason, but working with different personas would allow us to create guidelines for non-writers who were creating user-facing content.

Empowering a world where everyone writes

Another thing to worry about when creating internal documentation is how inclusive it feels to other disciplines. Remember, we now have 3 content designers in a company that has since grown to more than 2,000 employees. We need to influence the writing of hundreds of designers, engineers, etc. because, for better or worse, those are our real content creators.

To address this concern, I created specific sections in the content strategy for designers and engineers, with tailored feedback and ideas that would make extra sense to them because of the nature of their day-to-day work.

Finally, I wrote a section on prioritization. After all, you want to know whether I can collaborate with you as a member of your core team, right? This section may get updated as we hire a design operations person, who will have a wider view of our roadmap during the next year.

Getting buy-in means everybody wins

After making an initial draft, I reviewed it with different types of partners. First, my fellow content designers. Despite working on experiences for smaller businesses, still Gusto’s bread and butter, they were incentivized to help me be a success, because it could help them come up with content strategies for their own product areas.

Next, I shared it with my designers. They were already used to having to write their own content, and they were quite excited to see some new documentation to make this aspect of their job easier.

Finally, I shared it with product leaders at the company, including one of the cofounders. Gusto’s culture is such that most of our leaders have dedicated office hours, and they get plopped right on to our calendars, so it’s as open an invitation as it gets. One engineering leader in particular was quite excited to see I had created a flowchart to help people understand how we could help them and what they needed to do to get that help.

Rolling it out one team at a time

After soliciting all of this feedback, I then slowly released it to the company, first to my design team, then the entire design org, and finally the product org I work with. It was a real treat to see the head of the product org dive right in and leave a comment.

The very existence of this content strategy puts our discipline on the map in the same way that the components our design system team made put them on the map. When you ask someone their opinion, even if they speak on behalf of a team, it is still one person speaking to another. But when you point people to a reference, an artifact, now you’re talking about a thing, a seemingly immovable object.

And with that you get all the benefits that come with it. This is also often the result of creating and maintaining a comprehensive style guide.

All of these references are working together to create what our head of design refers to as a floor — that is, the minimum skill necessary to write in our voice and tone. Many companies talk about empowering non-writers to write for the product, but at Gusto we actually procure tools and resources to let it happen.

Next steps include implementing the rest of the feedback I’ve received, as well as making a content strategy guide for the entire company. It’s been quite a journey, but with everyone’s support it’s been much easier than it sounds to get the content design discipline where it needs to be here at Gusto.

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Joel Edelman
Gusto Design

Content design at Gusto, Team Instinct at Pokemon Go, southpaw sitter at the dinner table