Thimble
Design Research Case Study
Research that made one of Thimble's hardest steps simpler.
Contractors often need an Additional Insured on their policy to win a job, and many struggle to complete it. I tested two versions of the flow to decide what shipped.
Adding an Additional Insured, listing someone else on a Certificate of Insurance so a client will hand over a job, is one of the more confusing requests a first-time Thimble user runs into. To find out whether more visual guidance would help, I ran usability testing across three professional segments, comparing two versions of the same flow: one with a visual aid previewing the certificate, one without.
Who We Tested
Participants for this research came from a range of professional working segments: events & entertainment, consultants & freelancers, and handyman & contractor professions.
Chart: breakout of participants by professional category
The Baseline Flow
The first prototype was a step-by-step, progressive-disclosure flow for adding an Additional Insured, with no visual aid. Typically the user will have received instructions to add this as part of their coverage before they can take on the job.
Prototype 1: with no visual aid
Additional Insured Experience
Most participants were adding an Additional Insured for the first time, several arrived at Thimble specifically because they'd searched for how to do it. Only one was a recurring user who'd done it before without instructions.
Chart: how often participants had done this before
Instructional Format
Asked how they normally receive instructions from whoever's requesting the Additional Insured, the groups responded with a variety of ways they’d typically receive instructions to handle Additional Insureds on an insurance policy for a job.
Chart: how participants normally receive instructions
Group Sentiment for Prototype 1
Sentiment from the test group ran heavily positive, words such as "easy," "simple," "streamlined," "smooth," featured prominently against a much smaller handful of "confusing" or "stuck." The friction that did surface: checkbox language, and "Certificate Holder" reading as confusingly similar to "Additional Insured."
Chart: sentiment word distribution
Testing the Visual Aid
The second prototype integrates the visual aid directly into the experience, alongside the same step-by-step progressive disclosure approach from the first prototype. The visual aid is a preview of the Certificate of Insurance itself, shown to the user through the Additional Insured flow. It resembles the final output, and matches what's often provided to the user as a sample document in advance.
Prototype 2: with visual aid included
Measurement of Visual Aid Helpfulness
Reaction split almost evenly. One camp didn't see the point, the flow was already clear without it. The other wanted exactly that reassurance: a way to check the certificate without scrolling, and a confidence boost before submitting.
Chart: if the group found the visual aid helpful
Prototype vs. Current Experience
Measured against participants' current experience elsewhere, the visual-aid prototype read clearly positive: "better," "easier," "direct," with "wordy" the only real knock.
Chart: sentiment vs. current experience
This can be done in literally 20 seconds, whereas the other process took me maybe 5 minutes, that's tremendous time saving right there.
Deciding Factors
Asked to choose outright, most participants preferred Prototype 2, the version with the visual aid. Thimble shipped it: it cost nothing to include, and it mattered to the participants who did want that confidence check before submitting.
Chart: prototype experience preference
The Verdict
However they responded to the visual aid, participants were emphatic comparing either prototype to how they'd done this before, phone calls, generic platforms, waiting on hold.
Chart: Thimble prototypes vs. competitors, plus prior-provider experience
It's just handling one part of the policy at a time, so I don't have to call anybody
I just wanna go quick, quick, an image, done.
never as easy as Thimble.
Conclusion: One Step, Repeat Customers
Simplifying this one step brought customers back: we saw repeat policy purchases from it. That was one slice of the design practice I built at Thimble, and the imitators followed: other insurance platforms copied the UX I defined.