I started at HubSpot in 2010 as an Inbound Marketing Consultant, spending 6-8 hours a day on screen-sharing calls with our customers to teach them how to use our inbound marketing software to generate traffic, leads, and customers for their own businesses. I worked with companies ranging from cloud computing technologies to hotels in the Berkshires, but no matter their industry, one thing was clear: they needed a better way to learn to use the software with minimal hand-holding.
At the time, one of our high priority goals was to reduce customer churn by getting them to use our stickiest features. Yet no documentation or tutorials existed—customers depended on time-intensive 1:1 calls with their IMC to get set up and learn to make the most of our software’s functionality. Eager to optimize this onboarding process and improve usage, I spent nights and weekends building out the first iteration of HubSpot’s documentation until I turned it into a full-time role as a User Experience manager.
My documentation was easy to follow, using concise language organized by section headers and supplemented with annotated screenshots. When we’d launch a new feature, my colleagues would say “We need Diana arrows for this!” These step-by-step, detailed instructions made the onboarding process as foolproof as could be.

I also created the first iteration of a knowledge base called the HubSpot Learning Center, using HubSpot itself as its CMS. This is where we homed all the documentation I wrote and maintained, along with product update announcements and our latest group webinars.
Screenshot courtesy of the Wayback Machine.
As our software’s functionality quickly expanded, our documentation library was growing, and we needed an easier way for customers to search for an exact topic. So I pioneered the HubSpot Help Center, using Salesforce’s CRM to host this documentation since they had more robust search functionality.
Screenshot courtesy of the Wayback Machine.
I also expanded our documentation to include tutorials on inbound marketing methodologies, offering tips beyond our software’s functionality. Here’s one example article, which you can find on the Wayback Machine here.


Before I moved to HubSpot’s marketing team (as Head of International Marketing; I helped launch their first international office in Dublin), I also introduced the use of animated GIFs into the documentation to better illustrate functionality where appropriate.
While I can’t share detailed customer retention numbers, we did successfully increase usage of those sticky features and reduce customer churn over this time. And the Help Center, documentation methodology, and stylistic choices I pioneered are still in use at HubSpot to this day, which is exciting to see whenever I take a peek!