The Big Problem

Growth was stagnating in Hightail’s main product: file sharing and creative collaboration. My team’s objective was to expand the feature set to capture more of our user’s workflow with the goal of increasing subscription renewals.

Talking to Users to Learn How They Use Hightail

Hightail’s users were creative agencies who used our tool to collaborate on large media files. When interviewing our users, the PM and I learned Hightail was used as a companion with other products - design tools such as Photoshop and Illustrator and project management tools such as Asana and Basecamp. The workflow involved a lot of copying/exporting and pasting from one tool to another. Removing friction from this process was the opportunity we were looking for.

Two Approaches - Bring Hightail to Where They Work, and Bring Their Work to Hightail

Our main value prop, creative collaboration, was used primarily by our ‘Maker’ persona (the production artist, designers and videographer). Then we looked at who made the purchasing decision on tools - the Project Manager. By asking ourselves “What would be a compelling benefit for Project Managers?” we decided on a two-pronged approach: Streamline the Maker’s work by building a plugin for Adobe products (thereby speeding up production time), and building project management features inside Hightail to support the Project Manager’s work.

Bring Hightail to where they work with an Adobe Plugin.

Bring their work into Hightail by building project management tools into the product. This image shows the To-do feature

What would make a Project Manager’s life easier?

PM and I went back to our customers to learn more about the Project Manager’s role - specifically how they used their tools. We identified 3 features that would take care of 80% of the use cases they used in Asana or Basecamp:

1. To-Dos - Assign tasks to team members
2. Approvals - Work needs to go down an “Approval chain” before it could be shown to clients
3. Discussions - Single source of truth for decisions, team communication, and project-level file sharing

Approvals

Discussions

Flowchart to show how discussions is integrated into the rest of the platform

User testing during the design process

Design Mentorship

I led design on the Discussions, To-do’s and Approvals on our main desktop platform, but we also had work on the mobile apps (both Android and iOS), and the Adobe integration. These were taken on by the 2 other designers on the team. I communicated the goals and design vision to ensure a consistent end-to-end experience, as well as mentored and gave feedback when needed.

Company Impact

Shortly after the launch we were acquired by Opentext in 2018