Improving Engagement & Discoverability


Hightail, a feedback and project management tool for creative agencies and teams.

Role & Responsibilities

As the product designer on the core features team, one of my responsibilities is improving metrics on customer engagement. For this project, specifically, I found solutions for increasing the percentage of Spaces with comments.

The Problem

Since 2015, Hightail has been in the process of migrating customers from a legacy product to our new collaborative Spaces product. The habits of customers on the legacy product were primarily sending and downloading files, while our new product was focused on teamwork and collaboration on those files.

Prior to the migration, 15% of collaborative projects, called Spaces, contained at least one comment. Once the migration began, however, this number dipped to 5% as legacy customers entered the Spaces platform.

2016 was devoted to easing this migration and converting legacy send-and-download customers to share-and-collaborate Spaces customers. One of these projects was adding general commenting to files, where before we only allowed users to comment on specific regions on a file.


Before this project began, commenting required users to have moderate familiarity with the product and its UI. A user would start a comment by clicking directly on the image.

File commenting before in empty state

For first-time users, the act of commenting was clear in the empty state (above) because of the helper text in the comment bar.

However, if comments already existed on the file (below), the only signal that a comment could be created was that the user’s cursor changed on hover over the file. This, of course, was a problem as more and more first-time users entered the platform.

File commenting before

Final Design

Detailed process write-up in progress

The images below show a solution that improved our engagement numbers as measured by percentage of Spaces with comments. By allowing customers to make general, non-region-specific comments on a file and always exposing a comment box, the affordance for creating a comment became clear, especially to first-time users.

Within a month of release in late 2016, The percentage of Spaces with comments increased from 5% and returned to the pre-migration level of 15%, with continued signs of increase.

File commenting after in empty state
File commenting after