Discovery
I spent the first two weeks prototyping all of the key flows the team wanted to explore. After that, I wanted to support the team by checking some of the product assumptions I'd made about enterprise customer needs against reality. But it wasn't obvious how I might do this, we hadn't signed any large corporate accounts yet so there was no one to interview.
I reached out to my design mentors at Google Ventures to think about how to approach user testing or research for enterprise buyers. In consumer work, I had a good pipeline for people to come in and work with prototypes, but none of this would work for a CTO type.
In the end we decided to work with the sales team as a proxy for more direct research.They were speaking directly to new CTOs, CMOs, and franchise owners each week. During the third and fourth week I created demos of the prototype flows I was exploring and asked the sales team to share these videos with potential enterprise leads.
After that, I learned the sales team didn't use the website with these leads and would often send custom powerpoints pitch decks via email and would go over them with sales leads during the call. I reached out to the sales team to see if I could offer design help with their pitch decks. Normally, this work would be outside of my role... but it helped me get into a learning loop with the sales process and better understand the buyers we were designing the product for.
The demo videos of the prototypes were a big hit and helped sell the product. At the same time I got a better understanding— via the sales team— of the enterprise problem space and types of people who would be using these new tools. Some franchise owners & corporate admins spent time doing more hands-on, troubleshooting type work and visited a different location each day of the week. Others mostly delegated and wanted local control with just enough constraints to keep things running smoothly.
With our current small & medium business customers, my access to customer insights was naturally more direct. I already had a good understanding of the pain points, but I worked with the customer success team to set up open-ended interviews to better understand their workflows. One finding was that many managers used their mobile app during peak hours and used the desktop version of the web app in the office during off hours. I decided I wanted to double-down on our idea to build UIs that focused on specific interactions for differentiated roles, to include different contexts of use for the same user. I started wireframing and prototyping new flows to create a more seamless handoff to the desktop version to mobile. I also began to explore the idea optimizing the mobile app for quick fixes that were temporary overrides to core settings, while some of the more permanent and consequential changes could be done on a laptop after closing time.