Context

While consulting for a large company that was considering Atlassian tools, I noticed a big problem. They needed to train 120,000 people across different countries, but the only option was classroom training for just 12 people at a time. Atlassian quoted $6.5 million for this training, which seemed absurd. This gap between what companies needed and what was available sparked an idea that would shape the next five years of my career.

Challenge

The problem went beyond just logistics. Big companies were adopting Atlassian tools, but the training approach was creating a real bottleneck. We needed to rethink how people learn new software in large organizations. Without better training, companies risked poor adoption, wasted time, and ultimately failed implementation projects.

Approach

I used my experience in both technical work and teaching to create something new. Learn for Jira (L4J) delivered training right inside the Jira interface where people were actually working. At first, I did a lot of the work myself – product management, writing content, testing, customer support, and more. This hands-on approach was exhausting but gave me insights I couldn't have gained any other way.

As we grew, I focused on making learning fit naturally into users' daily work. We beat Atlassian University by keeping our content fresher, making it more engaging, and covering topics they didn't touch. We had to constantly adapt as both Jira and our customers' needs evolved.

Over time, I learned when to wear multiple hats and when to focus. Each role helped me understand how our product affected real people, but I also learned when to step back and let others take ownership as we grew.

Outcomes

L4J successfully solved a real problem, giving large organizations a way to train people efficiently right within Jira. We built versions for both Data Center and Cloud, and gained loyal customers who appreciated our approach. Eventually, I was able to focus just on product strategy rather than doing everything myself.

But perhaps what I learned most was recognizing when the market had changed. In 2021, Atlassian poured resources into improving their training platform. Our small team couldn't keep competing effectively anymore. Despite having an app customers loved and a cloud version nearly ready, I recommended we retire the product – putting the company's long-term health above my personal attachment to something I'd built from scratch.

Key Takeaways