These past couple months, I’ve been determined to get Cushion back on track after a much-needed “sabbatical”. Now that I have longterm stability from a full-time job (my team is hiring!), I’m also determined to do it the right way instead of blindly building new features and hoping that more people use it. I recently added analytics to help measure my changes and learn how Cushion hooks people. Unfortunately, a few years ago, I removed Cushion’s onboarding in favor of plopping them into the app with my fingers crossed and hoping for the best. Now, I’m eager to bring it back, but with the intention of being more thoughtful this time.

Over the years, Cushion has had a variety of flavors when it comes to onboarding. Originally, there was the step-based onboarding, which in hindsight actually worked really well. Then, I switched to an in-app checklist, which fell short because many of the items didn’t apply to certain users’ needs. At some point along the way, when I wasn’t writing as much about the process, I removed onboarding entirely and replaced it with suggestion links in each section. The idea was to remove any friction between the user and using the app. If they needed guidance on where to start, the suggestions are there for them in the relevant sections. It’s not an entirely bad idea, but because the suggestions are simply external links to support docs, the experience isn’t as ideal as something like an interactive, in-app guide.

Along with easing people into Cushion, the other reason I want to bring back onboarding is to learn more about the folks who are signing up. A while back, I had an idea to set up “profiles” where people could indicate relevant info about themselves, like whether they’re new to freelancing or a longtime veteran, or whether they’re a designer, a developer, a writer, etc. The end-goal was to send out an annual “census” about the freelance world—back when I envisioned Cushion having hundreds of thousands of users.

I still like the idea, but now I’m realizing that these profiles could also help Cushion reshape itself to guide people better. Rather than a one-size-fits-all approach, Cushion could emphasize certain parts of the app based on your profile. In parallel, I could learn from the profiles and potentially discover if a specific type of freelancer is hooked by Cushion the most. That could then guide me in shaping Cushion’s roadmap. I’m sure there are plenty of folks reading this and rolling their eyes at how obvious it is, but again, when you’re heads-down building features all day, you forget that assumptions and intuition can only get you so far. It’s okay to have assumptions, but it’s better to have a way of testing them and results to back them up.

Aside from using these profiles to inform how I should improve Cushion, I’m also simply curious—I love getting to know the people who use Cushion. Believe it or not, whenever I chat with a user in support, I often check out their website to see their work. Sometimes, I’m even familiar with it already! This angle of Cushion makes it much more than an app to me. Sure, I’m building a business that makes money, but I’m also building connections to these people—especially the ones who’ve been with Cushion since the start. I’m so grateful to be able to do this for a living.